Welcome back I'm Matt chemist today we're going to be discussing why we need specific vitamins how they work from a biochemical perspective and we're going to explain the various roles that vitamins can play in our cells what are vitamins and why are they called vitamins vitamins are small organic molecules which our body needs to be able to carry out its regular cellular processes vitamins are precursors which Become cofactors and coenzymes these are used in enzymatic processes processes involving enzymes when were vitamins discovered when vitamins were discovered they were thought to be vital amines although this
is a misnomer as several of the vitamins are actually not in fact amines for example let's start with the first vitamin vitamin A vitamin A has no nitrogens in it therefore not an amine thanks biologists vitamins are essential micronutrients that our body needs to Survive how you might ask we'll discuss this in great detail in the video essential nutrients can't be synthesized by our bodies either not at all or at least not insufficient quantities and therefore vitamins must be obtained through our diet I really like to use specific words like vitamin instead of they but
we're going to say vitamin like a billion times in this video so I'm sorry ahead of time the initial discovery of vitamins occurred in 1910 When umataro Suzuki a Japanese scientist discovered thiamine vitamin B1 as a complex of several B vitamins in following years more vitamins were discovered and what we classify as a vitamin has changed over the years while vitamins were only relatively recently discovered a little over 100 years ago it's been long known that we need to eat specific types of food regularly in our diet in order to stay healthy there are two
main groups of vitamins Water-soluble ones and fat soluble ones water-soluble vitamins include the B vitamins B1 B2 B3 B5 B6 B7 B9 and b12 another water-soluble vitamin is Vitamin C in addition to the water-soluble vitamins we also have fat soluble vitamins these include vitamins K e d and a in general fat soluble vitamins can be stored in the body and they're less likely to cause a deficiency and more likely to cause toxic City due to hypervitaminosis an excess of vitamins In the body since these are fat soluble they take longer for our body to eliminate
so unnecessary over consumption of fat soluble vitamins is something you want to avoid in the case of water-soluble vitamins these are more likely to be deficient in the body as the body is readily able to eliminate any excess in the urine our water-soluble waste removal system see you guys so far it all makes sense it's less likely that water-soluble vitamins Are going to be present in toxic levels since our kidney is able to eliminate them so rapidly water-soluble vitamins aren't stored in the same way with the exception of vitamin B12 which is stored in the
liver we often refer to different vitamins such as Vitamin K as one vitamin some vitamins can actually occur in a variety of different forms often referred to as vitamers some vitamins may be more readily absorbed and they also may be processed differently in the Body this video is sponsored by bespoke post bespoke post is a monthly membership club delivering a box of Awesome with top shelf goods from under the radar Brands it's free to join and you can skip a month or cancel anytime ninety percent of the products come from small Brands many of which
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and enter that chemist 20 at checkout or go to bespoke.com that chemist 20. that way they'll know you came from here I want to thank bespoke Post for their support of this channel the first chemical on this tier list is vitamin A vitamin A has several forms including retinol retinoic acid and Retinol different forms of the same vitamin are frequently referred to as vitamers in addition our bodies able to convert the different forms of vitamin A including retinol and retinol but not retinoic acid to the various different forms it needs for the specific biological processes
it's involved in because vitamin A is fat soluble that means that toxicity is more likely since it gets stored in the fat and it's not readily excreted the main nutritional Sources of vitamin A include animal sources such as egg yolks liver oil and meat as well as cheese and butter hey these are all fats vitamin A is fat soluble this all just makes perfect sense now in terms of absorption our body is able to absorb vitamin A as Vitamin A Esters this is cleaved by an enzyme called carboxyl esterase to form free retinol the alcohol
form of vitamin A as well as fatty acids the free retinol is reisterified in the small Intestine by an enzyme called lecithin retinal acyl transferase and this gets stored as a retinal faster in the liver remember it's fat soluble so the liver is just storing it for us while hyper vitaminosis can occur from excess vitamin A in the body the synthesis of vitamin A in our body from carotenoids such as beta-carotene is well regulated so there's no risk for hyper vitaminosis a assuming that you're a normal person with normal enzymes when consuming Beta-carotene normal levels
of the alcohol form of vitamin A retinol in the blood are able to suppress the expression of s-c-a-r-b-1 and bco1 beta-carotene 1515 Prime dioxygenase the enzyme that transforms carotene into its corresponding diol this dial gets converted to two equivalents of the resulting aldehyde and this resulting aldehyde is retinol this is the form that our body uses in our eyes now let's talk about the functions of vitamin A in The body vitamin A is used by our eyes in the protein rhodopsin rhodopsin forms an immune which is also known as a shift base with CIS retinal
this is an isomer of the fully trans retinol that our body is able to absorb the CIS form is photosensitive when our eyes receive light this is detected by the CIS retinol that's bound to the rhodopsin when the light is detected this causes a chemical reaction to occur where the CIS alkene is photochemically converted to The trans-alkene once the all trans product forms this is released by rhodopsin and it's reconverted back into the CIS form this is the specific part where it might be too complicated so I'll give the more complicated explanation now this is
photosensitive and upon excitation by Photon I.E the perception of light CIS retinol is converted back into trans retinal this is released by rhodopsin back into the retinal epithelium and converted back Into CIS retinol in addition to its role in the eyes vitamin A has some other biological functions including in gene regulation normal bone and teeth growth as well as normal cell differentiation when the body experiences a vitamin A deficiency which is rare it's possible to experience night blindness in addition to night blindness other effects include metaplasia keratinization bone and teeth problems as well as immunodeficiency
or Infections while you might be concerned that you have vitamin A deficiency unless you've been diagnosed by a doctor you shouldn't make any assumptions in fact it's possible to have hypervitaminosis a due to an excess of vitamin A in the diet some symptoms of acute hypervitaminosis a include headache blurry vision nausea and vomiting chronic hypervitaminosis a can lead to symptoms such as weight loss anorexia nausea and vomiting as well as Fractures there are some clinical uses of vitamin A topically it can be used to treat mild acne it's also available orally however this is only
used to treat severe cystic acne there are some other medications such as Accutane which look a lot similar to some of the beta-carotenes or vitamin A if you're interested in hearing a whole video about carotenoids in the future such as astaxanthin Accutane leave a comment down below and maybe that's something we Can do vitamin A is the single most important cause of childhood blindness in developing countries food fortification has been successful so much so that vitamin A intervention has been removed from research and into programming fortification is most prevalent as an additive in cereal and
is implemented in South Asia although its inclusion is optional in America and Canada you might have heard of this stuff before there's this product called Golden rice it's still on the market and you might be able to find it somewhere this was genetically modified to increase the amount of beta-carotene that the golden variety originally contained it's claimed to make up to 23-fold more beta-carotene than the plant originally would have as far as I know that's all bioavailable but for some vitamins they may not be in their bioavailable form you might be wondering what bioavailable means
so just because The nutrient is bound to some part of the food you eat doesn't mean that it's released later on in this video we're going to be talking about some other vitamin deficiencies where the vitamin was already there it just wasn't bioavailable so back to the golden rice while this may make more of the beta-carotene than the rice originally did it doesn't solve any of the other nutritional shortcomings that consuming a solely rice diet would have personally I don't know if this is very useful the idea of this rice was that as it has
more beta-carotene it's going to solve this vitamin A deficiency that certain places in the world suffer from usually due to Poverty or consumption of food which is lacking in vitamin A the product unfortunately wasn't a success and since it didn't sell you could say that the owners experienced a golden shower this product was developed by the Rockefeller foundation in my mind I look At the problem of vitamin A deficiency as one that you might be able to solve with local Solutions sure Gene modification could work if you want to do genetic modification of a plant
to make it produce use more of a specific vitamin I don't have any issue with that but you know what's more pragmatic probably just finding local carotenoids in the environment and teaching people to eat those carotenes exist in many different forms in the environment and a Lot of different plants can produce carotenes so if a bit of plant botany was done and suitable edible plants were identified that contained carotenoids this might be a far more pragmatic solution since you don't have to develop and distribute a new plant you can just take advantage of the carotenoids
that a local plant already produces maybe there's issues with that approach and if you have any opinions I'd love to hear them down in the comments another Interesting thing about vitamin A is that doctors have to be really careful when prescribing vitamin A to female sex patients of childbearing age as they could be pregnant and vitamin A can be teratogenic and it's an abortifacient that means that it's saying that you definitely want to avoid we've given a lot of time talking about the biology but let's talk about the chemistry of vitamin A retinol is a
polyunsaturated poly conjugated compound with a terminal Alcohol group when a synthetic chemist sees this many double Bonds in a row we know we're going to have a bad time it's quite impressive that bco1 is able to do that selective oxidation of beta-carotene a lot of the time in chemistry we have tools to selectively react with specific functional groups but nature is way better than organic chemists at doing chemistry selectively vitamin A is an important nutrient in terms of being a vitamin it plays an Important role and it's necessary in the diet I know you're probably
thinking Joey it's vitamin A we already are expecting you to put it in a tier and you're right vitamin A can go right into a tier the next chemical in this tier list is thiamine also known as Vitamin B1 some other forms of thymine other vitamers include thiamine monophosphate and diphosphate there's another chemical that has a similar name to thiamine called thymine thymine is a nucleobase In DNA synthesis thymine is different than thiamine for clarity I'll try to say thiamine as clearly as possible in North America most flour is fortified meaning that it usually has
vitamin B1 B2 B3 and B9 added to it the main nutritional sources of vitamin B1 aside from fortified flour include egg eggs non-refined whole grains yeast meat vegetables and nuts the processing of grains removes the outer layer where the vitamin B1 is contained as a consequence Of this processed flour that hasn't been fortified is deficient of the B vitamin that would be contained on the outside of the grain as such it probably isn't surprising to you that the consumption of solely white rice in your diet can lead to the development of vitamin B1 deficiency While
most flour and cereals are fortified it's possible that if you're a Celiac and you're consuming a gluten-free alternative that your flour might not be fortified so this is an Important thing to look into as you might not be getting the vitamins that you need in your diet and this is something you might want to consult the doctor about the B vitamins are water soluble that means that they're more likely to be deficient in the diet and they're less likely to cause toxicity since vitamin B1 is one of the B vitamins this is going to be
a water-soluble one for most of the metabolic reactions in our body we need To be using the phosphorylated forms of thiamine which for the most part is thiamine diphosphate the most important role of thiamine is for the product section of acetyl-coa from pyruvate acetyl-coa enters the TCA cycle and this eventually results in the production of nadh in the cytoplasm depending on the different energy sources that you consume your body can still produce energy now what do we mean when we say that well in this case the breakdown of Fats sugars and proteins all result in
the formation of alpha keto acids usually these Alpha keto acids are in the form of acyl coas and our body is able to use this to produce nadh which can be used to generate ATP earlier on I mentioned that the consumption of white rice solely could cause vitamin B1 deficiency what is vitamin B1 deficiency this is a syndrome known as berry berry there are two different types of beriberi there's dry berry berry which Involves neuropathy and there's wet berry berry which involves dilated cardiomyopathy another case where beriberi can arise is in Alcoholics if you're interested
in why vitamin B1 deficiency can occur due to alcoholism I'd encourage you to check out the recent video that we made on neurotoxins alcohol is a neurotoxin that depletes vitamin B1 and we talk about that out a little bit more in that video in terms of biological functions vitamin B1 is a Cofactor in biochemical reactions that result in the production of ATP the main role that it plays is for the transfer of two carbon units this is done with a dehydrogenase enzyme because it makes acetyl COA from pyruvate the acidyl group is the two carbon
unit of acetyl-coa additionally thymine can be used as an N heterocyclic carbine precursor in synthetic chemistry as it forms this really neat thing called a Breslau intermediate which has a ton of Synthetic utility for organic chemists when you take something like an aldehyde and treat it with a carbine such as the one that vitamin B1 forms it can form this neat thing called a Breslow intermediate this gives you the synthetic equivalent of an ACL anion and you don't have to do any sort of crazy deprotonation to generate an acyl anion in fact acyl anions aren't
actually stable which is why we have synthetic Alternatives such as the Corey seabock Reaction although we just access this for free using something we find in nature this acyl anion equivalent can be functionalized to generate a lot of different interesting products similar to how vitamin B1 is able to form a Breslau intermediate with aldehydes our body is actually able to react vitamin B1 and this enables decarboxylation reactions one example of this is the generation of acetyl-coa from pyruvate where initially the carbine is able to Attack the Ketone and the molecule can undergo a decarboxylation reaction
the resulting anion is stabilized and it can actually be drawn as a Breslow intermediate all we really did here is access an aldehyde through a decarboxylation reaction thanks to thiamine thanks biology this one's actually pretty cool when we're producing acetyl COA thymine diphosphate is used during glycolysis to produce acetyl-coa using pyruvate dehydrogenase Magnesium as well as nadh nadh is another important cofactor that we're going to get to later on when we discuss niacin this reaction generates an equivalent of nadh and this is the reduced form of NAD plus that nadh is about to be cold
Hard Cash in the electron transport chain of the mitochondria the U.S stock exchange of the cell if you're not sure what a dehydrogenase is this just involves decarboxylation as well as conjugation With COA COA is another important molecule that we're going to get to a little bit later in addition to glycolysis thymine is used in the Krebs cycle acetyl-coa is like the digital funds that are in a holding account which your cells are going to use to buy stock such as nadh this is a stock exchange after all I better have some stock analogies in
here the other cofactors and coenzymes in this process are like the People who broker the deal One example is the enzyme alpha-ketoglutarate dehydrogenase this is where the exchange happens the enzyme which is essentially The Exchange here is alpha-ketoglutarate dehydrogenase alternatively this is also used in Branch chain Alpha ketoacid dehydrogenase there is also a couple other Pathways such as the hmp shot in transketalase but we're not going to get into that since B1 is involved in the synthesis of nadh it finances the Mitochondria ATP baby let the cash flow now let's talk about the chemistry of
vitamin B1 a bit vitamin B1 has a pyrimidine ring as well as a thysolium but when this is deprotonated it forms a carbine we also have an alcohol group and this amino group take off here overall I think the chemistry of vitamin B1 makes me think it's pretty neat and when I learned about the whole formation of a Breslau intermediate you know I am a chemist after all I got super stoked About biochemistry so for that reason vitamin B1 got me hyped about biochemistry I think we could put vitamin B1 right into s tier next
we have another B vitamin riboflavin if you like yellow chemistry riboflavin is the vitamin for you foreign is trash if it's yellow it's trash and your synthesis doesn't work if your synthesis at any point goes yellow it just stops working all right confirmed Fat riboflavin comes from the root Flavio which means yellow vitamin B2 has three forms including riboflavin Flavin mononucleotide and Flavin adenine dinucleotide these are known as fmn and fadh accordingly fmn and fad are cofactors derived from riboflavin and vitamin B complexes it's possible to get your vitamin B through enriched grains such as
wheat flour although it's also possible to take B vitamin supplements Which contain lots of vitamin B2 if you want natural sources yeast eggs and mushrooms all have lots of vitamin B2 vitamin B2 enters the body bounds to albumin and first it must be cleaved by hydrochloric acid in the stomach and absorbed in the duodenum or duodenum if you prefer vitamin B2 toxicity is less likely once again this is another B vitamin and all the B vitamins are water soluble riboflavin deficiency is rare in North America this is likely because we Fortify our food some causes
of riboflavin deficiency include malnutrition such as in abject poverty anorexia nervosa and aversion from drinking milk this could be because you're lactose intolerant there's ribose Flavin and milk if you drink less milk because the milk can be damaged by UV you end up absorbing less of the B2 it's also possible that you have normal intake but you have decreased consumption this could be due to IBS Celiac disease ocps long-term barbiturate use or MADD riboflavin is also used as a yellow orange food coloring now we're going to be talking about riboflamin a little bit later on
I apologize if you're looking forward to the biochemistry here in terms of the chemistry of vitamin B2 it has this interesting Motif which is a quinox saline however it's also a teradene so technically it's a benzoterridine this is derived from GTP and it's Biosynthesized in bacteria there's also a Tetra alcohol which we call a tetral side chain and the terminal alcohol is phosphorylated to give fad and fmn I think that vitamin B2 is a little bit less cool of a vitamin there's a couple cool redox processes overall I think because vitamin B2 is fairly easy
to get enough of in your diet as long as you're eating a variety of foods or you're supplementing to make sure you get the right amount I think that vitamin B2 2 Can probably go into like d tier not a very interesting vitamin at least not yet next we have vitamin B3 vitamin B3 occurs in several different forms including in niacin niacinamide or niacinamide riboside here we have niacinamide another name for this is nicotinamide but when you hear nicotinamide you probably think nicotine and we're going to get to why that is in a little bit
there are many many sources of vitamin B3 in the diet as our body is Also able to synthesize vitamin B3 from tryptophan niacin's also added in enriched foods when you're deficient of vitamin B3 you get a disease known as pellegra the three main symptoms of pellegra include diarrhea dermatitis and dementia there's also a fourth D if you include death the most common cause of vitamin B3 deficiency is from eating only a Corn based diet where there's no niacin or tryptophan in fact tortillas actually save Latin America from Pellegra people realized that niacin is actually present
in the corn but it's not bioavailable so it was necessary to treat tortillas with base to release the niacin and make it bio available there's actually a great video for medicosis perfectionalis and I'll include a link to that in the description if you want to hear the whole tortilla story so back to the part about nicotine niacin used to go by the name nicotinic acid as we started discovering vitamins just around 100 years ago since it used to be called nicotinic acid when the government started making fortified wheat flour two conspiracy theories popped up people
thought that nicotinic acid was the same as nicotine here's a structure of nicotinic acid here's the structure of nicotine you can see that they're kind of similar but only in the sense that they have a pyridine ring and that there's something sticking off in the three position shown here so the Conspiracy theories were that people thought that the government was putting tobacco in bread the other thing that people thought was smoking gives you vitamins both of those are not true as such the AMA changed the name to niacin so that people who didn't know what
nicotine and nicotinic acid were stop thinking dumb things the United States introduced the addition of niacin to grain in 1940. it's currently produced synthetically through the Oxidation of three cyanopyridine when niacin fortification was first introduced niacin was typically extracted from natural sources such as liver and yeast usually niacin deficiency occurs due to abject poverty alcoholism and anorexia niacin seems like pretty boring right it's just a ring with an acid or an amide but it's actually really useful because niacin is used to make NAD and nadp recall these are some of the stock choices that the
Mitochondria has NAD plus and nadp plus are like the stock when the price is low and when they get converted to nadh and nadph this is like when the stock is high in value now let's talk about the chemistry of vitamin B3 overall it's pretty simple it's just got a pyridian ring and an a amide or an acid depending on which form it is so I think as a vitamin goes chemically it's pretty boring but once it's been converted to nadph or nadh it becomes way more Interesting some of the reactions that this can do
that you can see later on are really interesting so why don't we put this into s tier the next vitamin is vitamin B5 what the heck B5 do we just skip vitamin B4 yeah there used to be a bunch of other ones but somebody decided that they're not vitamins anymore and maybe that's something that we'll talk about in a future video okay vitamin B5 is also known as pantothenic acid or pantothenate you might be thinking those Are two different things one of them is an acid and one of them isn't an acid and in chemistry
and biology we often refer to acids as well as their base form by different names in this case pantothenate is just the conjugate base of pantothenic acid and it'll have essentially the same properties biologically once it gets absorbed into the body it'll get converted into the relevant forms and biology tends to figure out a lot of stuff on its own the Name literally means from everywhere so pantothenate can be found almost everywhere vitamin B5 is not Amanda food fortification in any country although most cereals are fortified with 100 of the daily value of five milligrams
another vitamer of B5 includes pantothenic acid pantothenic acid is used to make coash or COA this is different than acetyl-coa this is just the COA so the COA part of acyl COA is only able to be made using vitamin B5 This is what COA looks like and this is what acetyl-coa looks like now in terms of deficiency and toxicity for vitamin B5 both of them are extremely rare however when it comes to the chemistry vitamin B5 itself is pretty simple all it has is a couple alcohol groups in amide and a carboxylic acid however if
you look at the structure of COA I would rather become a biologist than synthesize that this one's pretty simple it is used for COA And COA is pretty cool I think this probably can go into like a tier because acetyl-coa is pretty awesome and you can't make acetyl COA without COA so we have to use vitamin B5 at least a little bit all this is really doing for almost all of its function is just as a Linker though so maybe that's actually kind of boring I'm just going to leave it there it's simpler here we
have vitamin B6 I think vitamin B6 is probably my favorite vitamin because the mechanism of its Chemical reactivity is just so incredible and we're going to be discussing it shortly vitamin B6 is found in several different foods including Meats yeast plants fish egg yolks and even more food sources there are three different vitamins of vitamin B6 including pyridoxine pyridoxamine and pyridoxyl pure oxal 5-phosphate is the main metabolically active form of vitamin B6 this is a coenzyme used in more than 140 enzymatic reactions for The metabolism of amino acids glucose as well as lipids this is
probably going to be an S tier vitamin plants actually synthesize pyridoxine as a means of protection from UVB which they are exposed to through sunlight Vitamin B6 is also used in the synthesis of chlorophyll while including vitamin B6 as a food fortification isn't mandatory in any country most cereals are still fortified with 25 of the daily value 0.5 milligrams this is also a cofactor for Transamination reactions as well as decarboxylation reactions and these are the things that get me fired up about vitamin B6 transamination is this really cool process where we start with an amino
acid as well as an alpha ketoacid this could be an alpha keto acid like we talked about earlier such as pyruvate or alpha-ketoglutarate what happens is the initial amino acid is converted into an alpha ketoacid and the alpha keto acid is converted into an amino acid this Occurs through an enzyme mediated process where the initial iminium which is stabilized by the ortho-hydroxy group is able to isomerize transferring the oxidation state of the vitamin B6 and oxidizing the amino acid to an alpha ketoacid once this new Amino version of vitamin B6 is generated it's going to
get converted back to the aldehyde one example of this would be if we converted alanine into pyruvate or similarly aspartate gets converted into Oxaloacetate often times when we see an amino acid and want to convert it to the corresponding amine vitamin B6 is also involved with these one example of this is the decarboxylation of 5-HTP into serotonin 5-HTP is just 5-hydroxytryptophan and the generation of 5-hydroxytryptophan is actually mediated by another vitamin vitamin C and we're going to be talking about that a little bit later another important biochemical process that I really want To highlight here
is that vitamin B6 is needed to synthesize vitamin B3 out of tryptophan through the kineurine process now in terms of the chemistry of vitamin B6 it's pretty cool several of the functional groups have roles in the chemistry of vitamin B6 it's essentially doing reactions that synthetic chemists can only dream of it has a pyridine ring with an aldehyde or an alcohol group and depending on the form that it's in it can do all sorts of different things This one's super duper cool this is going to go right into s tier the next vitamin is biotin
I know someone who really likes biotin don't you Garrett vitamin B7 is also known as Biotin and biotin deficiency is actually really rare since it's common in most Foods one way that biotin deficiency can occur is through the consumption of raw egg whites raw egg whites contain a protein called avidin and this is an anti-nutrient that prevents the Absorption of biotin vitamin B7 is not a mandatory food fortification the average biotin intake from Foods in other Western populations is about 35 to 70 micrograms per day indicating that most people in these countries consume adequate amounts
of biotin biotin is used for carboxylation reactions one example of this is the conversion of acetyl-coa into melon COA this is a bit weird from a chemistry perspective because for vitamin B7 to fulfill its Role it first must carboxylate one of the urea nitrogens of biotin biotin has a urea group it has a tetrahydrothiopine as well as carboxylic acid which is usually bound to stuff I don't think vitamin B7 is as cool it's got kind of a weird reaction mechanism where it gets carboxylated but overall I just don't think it's that cool of a vitamin
biotin can go right into F tier I mean there's sulfur in it and biologist Tate sulfur you might think it's just the smells but No biologists hate doing any conjugation work but I'll just either okay whatever I gave up on trying to say something anecdotal there the next vitamin is vitamin B9 also known as folic acid or folate similar to how pantothenic acid and pantothenate were two forms of the same thing folic acid and folate are similarly named when folate is consumed it's usually in its oxidized form as shown here however for it to carry
out its biochemical processes it has to be In its reduced forms dihydrofolate or tetrahydrofolate tetrahydrofolate can be abbreviated to thf and this is something that biologists frequently do unfortunately chemists also have an abbreviation thf and this is for tetrahydrofuran this means that chemists get really confused when they take a look at biopapers yes this is a really common thing I'm definitely not just talking about me thf WTF there are several different forms of folate in the Diet and it's usually found in green leafy vegetables regulations for mandatory fortification of wheat flour with folic acid are
currently in place in 53 countries similarly in Canada the mandatory fortification of foods with folic acid was introduced in 1998. according to medicosis perfectionalis who's a trained physician most doctors will almost never see patients come in with vitamin B deficiencies like someone who watches this will have a vitamin B Deficiency and I really don't want to discourage them from going to the doctor because someone for sure will be no matter what I talk about someone who's watching is somehow able to relate to the craziness in every single video in terms of function folic acid and
folate are involved with the transfer of one carbon units in DNA synthesis and cell replication tetrahydrofolate is used to transfer methyl group to vitamin B12 vitamin B12 further donates this methyl Group to sign called homocysteine and this is how our body is able to make methionine now in terms of the chemistry of vitamin B9 it has this interesting Motif called The territin Ring We briefly talked about teradian Rings earlier when we are discussing vitamin B2 riboflavin there are other roles of tetrahydrofolate in the body aside from the transfer methyl groups although we're not going to
get into this now overall I think this is a pretty basic Vitamin it isn't too too interesting but it does transfer methyl groups and that's kind of cool I guess I think we could put vitamin B9 into like C tier because it helps vitamin B12 do its job but other than that it's a bit underwhelming speaking of vitamin B12 why don't we talk about vitamin B12 this is one of the coolest B vitamins and from an organic chemistry perspective we're starting to see more and more biomimetic processes this just means a Process that mimics biology
a recent example of this is the development of sh2 catalysis which can utilize processes that mimic vitamin B12 vitamin B12 comes in several forms a couple examples include cyanocobalamin hydroxycobalamine methylcobalamine and adenosylcobalamine vitamin B12 is an important cofactor in DNA synthesis as well as fatty acid and amino acid metabolism fortification of vitamin B12 is not required in the US and Canada However New Zealand Australia and the United Kingdom require cereals in and some plant-based milk alternatives to be fortified with B12 mandatory fortification of the B vitamins produce neural tube defects by 30 to 50 percent
now in terms of the chemistry of vitamin B12 there is a lot to talk about if you think that vitamin B12 has interesting chemistry there's actually a fully recorded lecture on YouTube from Woodward himself Woodward and eschenmore Completed the total synthesis of vitamin B12 in 1972. if you want to know what a research talk was like in 1972 I'd encourage you to check out that whole video there's even a couple spicy bits in it I think because the chemistry is so so cool and I know I'm really not doing it justice in this video by
talking about it we're going to have to put vitamin B12 right into s cheer R matey have you heard of vitamin C how about ascorbic acid because that's Another name for vitamin C this is not citric acid yes citric acid starts with a C yes citric acid is found in citrus fruits but so is ascorbic acid vitamin C both are still present in citrus fruits while citric acid is present in large amounts vitamin C is actually present in relatively small amounts there are some other other forms of vitamin C aside from ascorbic acid including ascorbate
which is the base form of ascorbic acid and the oxidized form of ascorbic acid Dehydro ascorbic acid unfortunately vitamin C is destroyed in cooking and storage as well as processing so usually vitamin C needs to either be formulated or consumed fresh maybe that means you want to eat a fresh orange once in a while vitamin C is only found in fruits and vegetables especially citrus fruits in the United States vitamin C fortification is not mandatory however most Nations have adopted specific regulations with an upper and lower Limit for certain foods such as in Canada ascorbic
acid is mandatory in fruit flavored drinks infant formula diet foods meal replacements instant Foods evaporated milk milk and dehydrated potatoes hypervitaminosis C is rare since it's another water-soluble vitamin and deficiency of vitamin C causes scurvy and modern pirates can get scurvy too you might have heard before that vitamin C is effective against the common cold this was a misconception Stated by Linus Pauling and it's not true so just because you got a Nobel Prize doesn't mean you're right about everything okay now with a couple vitamins on this tier list they qualify as antioxidants vitamin C
is considered to be an antioxidant however this is one that your body can actually use to reduce oxidative stress this is one that your body literally uses inside cells and we know that this works while this is technically true it's a bit of an Oversimplification because when vitamin C reacts with free radicals it produces the oxidized form dehydro ascorbic acid the oxidized form has to be reduced back to the active form after it's been used it's actively imported into the endoplasmic reticulum of cells via glucose Transporters once it's in there it's reduced back to ascorbate
by glutathione and other thiols hey remember how earlier we were talking about nadh and nadph while nadph is the Reductant which reduces glutathione disulfide back to glutathione and glutathione is what reduces the dehydro ascorbic acid back into ascorbic acid so technically nadph is the antioxidant here and where do we get nadph from that's right the burning of energy so how do we get antioxidants we burn energy and in fact that actually makes sense if you think about it because for our mitochondria to produce energy we have to use oxygen and oxygen is an Oxidant so
to use the oxygen we have to reduce the oxygen that's why we have the electron transport chain some functions of vitamin C in cells include the hydroxylation of collagen in the rough endoplasmic reticulum this is a type of post-translational modification and when collagen is less hydroxylated it's less stable and this is what leads to some of the symptoms of scurvy specific residues of the collagen that are hydroxylated include the conversion of Proline into Hydroxyproline as well as the conversion of Lysine into hydroxy lysine now because these are protein bound this is happening to the protein
after translation after the protein has been made this is a post-translational modification you remember earlier how we were talking about dihydrofolate and tetrahydrofolate well vitamin C is also needed to reduce folate into dihydrofolate and tetrahydrofolate so vitamin B9 needs vitamin C to be able to Do its job earlier on I mentioned that vitamin C was needed to convert tryptophan into 5 HTP 5-hydroxytryptophan this is eventually needed for serotonin before undergoing decarbox isolation with vitamin B6 if we look at the oxidized form of vitamin C you'll recognize that it looks cursed AF here we have a
one two three tricarbonyl and that's so crazy that one of the alcohol groups is able to like come around and attack and form this thing Called a lactol the other carbonyl is just like yeah sure cool I'll also add water to me in fact why don't I add water to both of these and even open back up again so that's pretty cursed vitamin C cursed starts with a C vitamin C is going to go right into C tier there is one other thing I didn't mention here vitamin C also resembles this cool acid called squareic
acid which is literally a square and while you might think Square acid is pretty cursed I still Think that dehydro ascorbate is way more cursed up next we have vitamin D also known as calciferols the D vitamins technically aren't even vitamins what vitamin D can be synthesized in adequate amounts by most mammals if they get enough sunlight so it's not technically essential and therefore isn't technically a vitamin instead it can be considered a hormone with activation of the vitamin D pro hormone resulting in the active form calcitriol which then Produces effects via nuclear receptors in
multiple locations vitamin D is mostly just a signaling molecule that our body uses as a hormone some vitamers if you can call them that for vitamin D include lumosterol ergocalciferol which is vitamin D2 colocalciferol which is vitamin D3 as well as some other forms vitamin D2 and D3 are the important ones that we need to consider in humans especially vitamin D3 in the early 1900s nearly 80 percent of children suffered From lowered bone density also known as rickets and a solution was proposed feeding Cod Liver to cows cod liver is rich in vitamin D and
feeding the cows the Cod Liver increase the amount of vitamin D in milk which thus decrease the occurrence of rickets this is something that's still done through several different ways sometimes this is introduced through the feed other times it's done through injections or another way can be done is through UVB Irradiation from the Sun or artificial lighting the vitamin D and feed can either be plant or fungi based ergocalciferol or alternatively it could still be animal-based cholecalciferol in terms of toxicity the toxicity of vitamin D is actually rather rare it usually occurs due to supplementing
with high doses of Vitamin D rather than getting sunlight in terms of the biochemistry vitamin D is used for managing calcium levels and it's a Ligand for the Vitamin D receptor which is a way to regulate DNA expression now in terms of the chemistry of Vitamin D it kind of looks like a steroid molecule that was smacked so hard that it ripped one of the Rings open because that's exactly how it's made initially we have Pro vitamin D3 this is excited by UVB and undergoes a retro deal zalda reaction forming this triene this triene is
able to undergo a thermal isomerization rearranging the position Of the double bonds through an in-like reaction and the resulting vitamin D3 is able to be oxidized to calcitriol through two enzyme mediated steps calcitriol is a polyunsaturated trial and aside from that there's not too much to say other than it use to be a steroid vitamin D is a signaling molecule overall I think it's probably one of the more boring ones so we can put it into D tier and I swear guys I'm not just putting them in the letter that they Start with even though
some of them are but okay that has happened a couple times but that's okay you're patient because you're an S to your viewer next we have vitamin E vitamin E isn't actually one molecule it's a whole bunch of molecules when I was growing up we had this vitamin E cream that we would sometimes use when we had dry skin in my opinion it never really did anything it just made my skin gross and oily and guess what that's because vitamin E is a Fat soluble vitamin there's several different vitamins of vitamin E and these are
called Taco ferals you might have heard of vitamin E before in the form of vitamin E acetate sometimes people have added vitamin E acetate to Vapes and this is a really terrible idea because vitamin E acetate is something tolerated in food when eaten but when smoked or when heated to very high temperatures this can form something called ketine and ketine is extremely Toxic so you're creating this very toxic ketine gas in your lungs when vaporizing by vitamin E acetate this is a really terrible idea make sure you're not vaping any vitamin E acetate please please
please please please don't do that you might be wondering why is anybody dumb enough to do that well it turns out that vitamin E has similar physical properties to THC so sometimes people will try and make weed Vapes Cheaper by cutting it with vitamin E Acetate this is really dangerous and absolutely nobody should be doing this vitamin E comes from fruits vegetables nuts seeds and Seed oils deficiency of vitamin E is actually very rare it's worth noting though that there's a serious drug drug interaction with something called Warfarin vitamin E when it gets oxidized becomes
a quinone and in its quinone form it's an inhibitor of vitamin K dependent gamma hydroxylase this prevents your blood from Coagulating in addition Warfarin also prevents coagulation of blood so together when Warfarin and vitamin E are both being taken this can cause people to bleed too much when injured since both of them cause you to bleed more easily in most of the world vitamin E fortification is voluntary however in Canada it it's mandatory if there's a reduction in vitamin or mineral content due to processing in terms of biological importance vitamin E is one of the
other Cool ones one of the things it can do is sit around in the fatty acid membrane and react with reactive oxygen species it does this in red blood cells muscles nerves as well as in our retina this one's actually pretty clever biology initially what happens is a reactive oxygen species is able to get reduced by vitamin E to quench the radical and then the oxidized form of vitamin E is able to get reduced back by the body vitamin E is also used in the synthesis of Ubiquinone it's actually pretty cool if you look at
the oxidized form of vitamin E because this is able to oxidize ubiquinone in its ubiquinol form into ubiquinone it's oxidized form there's these two methoxy groups on the ubiquinone ring and these are electron donating groups because there's those two electron donating groups if we compare those to the methyl groups of the quinone of vitamin E the methoxy groups are just way stronger electron Donating groups so that means that TQ the oxidized form of vitamin E is actually a stronger oxidant than ubiquinone and this is why it's a favorable reaction to form ubiquinone vitamin E is
also used in the synthesis of DNA and RNA in terms of its chemistry vitamin E is actually pretty boring but the biochemistry that it does when oxidized and reduced is actually pretty clever when it gets oxidized it actually opens up the whole ring into a quinone However it can be reduced back to its closed ring form as needed vitamin E overall I think is pretty boring in terms of chemistry I think it's pretty cool that it sits around in the lipid membranes to prevent oxidation of fatty acids that's pretty cool overall I think the quinone
chemistry is pretty cool I like seeing oxidation reduction chemistry happening in biological organisms why don't we put vitamin E into B tier last but not least we have Vitamin K the Quinones it wasn't until I was working on this video that I saw the oxidized form of vitamin E and I realized how similar it was to vitamin K the only difference is that we have two methyl groups instead of a whole Benzene ring like vitamin k does vitamin E's oxidized form is a one for quinone while vitamin case quinone is a benzoquinone vitamin K stands
for coagulation it's used to help our blood coagulate bacteria in our gut produce vitamin K2 And there's technically three total vitamers of vitamin K vitamin K1 which is phylloquinone vitamin K2 which is monoquinone and vitamin K3 also known as menadion Vitamin K3 shouldn't be used in humans at least not according to health authorities in North America vitamin K fortification is not required by law in most countries for instance in the United States it's optional for food manufacturers to add vitamin K to their products similarly Canada has no Specific requirements pertaining to vitamin K fortification but
the nutrient is included in the general requirements for nutrient content claims and nutrition labeling in the European Union Vitamin K is only allowed to be added to certain types of infant formulas the K vitamins are fat soluble vitamins there are some other forms that are not found in nature which technically can't be considered vitamins vitamin K3 also known as menadion is a synthetic Compound that's sometimes referred to as Vitamin K3 this is used in the pet food industry because once it's assumed it gets converted into Vitamin K2 in the body of the animal however the
U.S Food and Drug Administration has banned this form from sale as a human dietary supplement because large doses have been shown to cause allergic reactions hemolytic anemia and cytotoxicity in liver cells now personally I think if we don't want that happening in people we Probably shouldn't be doing it in animals either or if we are doing it in animals hopefully it's not as bad for them as it is for us Vitamin K is used for carboxylation reactions specifically it's used for gamma glutamyl carboxylase where protein-bound glutamate is converted to carboxylutamic acid this is an uncommon
amino acid that's introduced into proteins by a post-translational carboxylation of glutamic acid residues one place where this modification is Found is in clotting factors and other proteins of the coagulation Cascade this modification introduces an affinity for calcium ions in the blood coagulation Cascade Vitamin K is required to introduce gamma-carboxylation of clotting factors 2 7 9 10 and protein Z overall I think Vitamin K is pretty simple it's an oxidant that our body needs for specific processes it's almost the same as Vitamin E in terms of structure I think we could probably put Vitamin K into
B tier as well so hopefully you've enjoyed this tier list about vitamins and hopefully you understand a little bit better why we need vitamins now thanks for watching and I hope you have a great day
