Talk:Adenine

Chemical structure

Adenine is a chemical with the empirical formula C5 H5 N5. This diagram is incorrect and needs to be fixed before putting back into article

This structure is incorrect. There should not be a double bond to the extracyclic amino group, but rather to the N in the ring (unless we want a bizarre resonance structure, but in that case we would need charges on the nitrogens).

Josh Cherry 21:39, 13 Oct 2003 (UTC)

I've removed the structure because, as I pointed out eight months ago, it is incorrect. Josh Cherry 14:09, 27 Jun 2004 (UTC)

So, I assume that you'll be uploading a corrected image, real soon now? ;-) Lexor|Talk 23:51, 27 Jun 2004 (UTC)

I agree with Josh. In my opinion, it is better to have no diagram than an incorrect diagram. Axl 18:58, 14 Dec 2004 (UTC)

Am I just being stupid, or is there no double bond attached to the extracylic amino group (I hope you're refering to the amino group on top of the six-membered—and aromatic, probably—ring?)? In any case, this current picture on the actual article and here on the talk page is consistent with what is in my textbook. Kr5t 02:13, 21 May 2006 (UTC)

Vitamin?

Is this a real vitamin or not? I assume it's not: It's not listed on the vitamin page, and that page is quite explicit that there are only thirteen recognized (human) vitamins. But this page is also listed under category:vitamins.

It was considered one, once upon a time, but it turns out it isn't. Kr5t 02:14, 21 May 2006 (UTC)

Diagram/content

Well, the diagram is wrong. I dont know what the right one looks like, but this doesn't have H5. Also, I think it's important to include other common biological molecues that have Adenine in them. This includes, but is not limited to NAD, NADH... yeah. Can't think of anymore off the top of my head but it's a start.

What's wrong with the structure? You mean that it doesn't have five hydrogens? It does. Two of them are implicit, according to the well established conventions for drawing structures (each of the two carbon atoms that would otherwise form only three bonds has a hydrogen substituent that's not explicitly shown).

There are tons of biochemicals that contain an adenine moiety. I don't think we should show all of their structures here. Josh Cherry 01:19, 11 Feb 2005 (UTC)

Wow, you're totally right. I don't know how I missed that, the structure is right. As to the adenine-containing biochemicals, I think it is important to at least mention some of these and link to sites about those chemicals. DavidMendoza 23:33, 20 Feb 2005 (UTC)

Just a side, note, it does have five hydrogens, three of which are implicit, not two. And by the way, if you truly think we should list all the adenine-containing compounds (including activated intermediates and nicotinamide compounds?) a category would probably be more appropriate. Kr5t 02:20, 21 May 2006 (UTC)

Part in article was wrong

In the article, it said that Adenine could form a base pair with thymine, but it also forms a base pair with uracil. Dogmanice 18:45, 19 March 2006 (UTC)

That's wrong...how? It can form a base pair with thymine, right? Besides (I don't know about what it looked like in your version) but right now, it's 100% correct. It's base pair in DNA is thymine and it's base pair in RNA is uracil.Kr5t 02:18, 21 May 2006 (UTC)

Tautomers

The diagram of adenine to the left of the text appears to inconsistent with that which appears on the right of the text (in the box with the SMILES and CAS number and other info). I recognize it as tautomers (correctly, I hope), but shouldn't we make a note of it? I hadn't even heard (read) of tautomers until earlier today, when I was studying SMILES. Kr5t 02:25, 21 May 2006 (UTC)

Chemical Structure

http://www.ca.uky.edu/agripedia/GLOSSARY/adenine.htm

Eukaryote bias in article

The way that the word cytoplasm is used in this article shows a bias against prokaryotic cells. By mentioning cytoplasm only at the RNA to protein step it suggests that the RNA is not generated in the cytoplasm but in a different structure. This is true for only a tiny fraction of all known lifeforms. Hcobb (talk) 00:08, 12 June 2009 (UTC)

Dietary Sources

I think this article should include examples of types of food that contain this vitamin. Any thoughts on that? Qbert203 (talk) 01:05, 28 February 2011 (UTC)

well I have thoughts yet I do not know if they are relevant I have read that a human typically creates then processes 90lb (45 kg) of atp continually recycling the molecular edenine core I wondered if creating a higher amount of adenine cores at a tissue would change the rate of atp recreation I have not looked this up note that most atp is regenerated from adp as well as amp Anyway I wondered if highly resilient energetic microorganisms would result from either their genes specifying higher adenine production or having adenine provided at the culture medium

If any of that is true then there could be a plausible reason that humans would supplement with adenine looking up "dietary adenine" gives a number of papers http://jn.nutrition.org/content/106/3/435.full.pdf (clifford story) suggest rats given lots of adenine get hyperuremia as well as get skinnier.

The rats fed food gained a few grams a day, the rats fed food with .75% adenine got skinnier The difference is rather noticeable It appears the adenine fed rats would weigh near half as much as the rats fed ordinary food around 83g with food "featuring" adenine compared with 178g with regular food.

rats may have weighed 94.5 g prior to feeding with food gained 6g per 24 hours * 14d = 84 grams heavier with food as well as adenine -.8g per 24 hours *14d = 11.2 g skinnier

from a human perspective adenine might cause hyperuremia as well as completely blocking gradual weight gain from feeding The rats on adenine peed about three times as much volume to get rid of the urea produced from adenine

The paper I read made adenine look like a mildly risky diet pill that could benefit women resistant to uric acid accumulations particularly people with a genetic profile like from 23andme.com (or a variety of other providers) that assures them they are resistant to gout It also suggests that vegetarians that like lentils might be particularly skinny.

The paper notes that lentils as well as peas have high adenine content http://jn.nutrition.org/content/106/3/435.full.pdf — Preceding unsigned comment added by Beanangel300 (talk • contribs) May 16, 2011

Watson & Crick image

Adenine on Crick and Watson’s DNA molecular model, 1953. The picture is shown upside down compared to most modern drawings of adenine, such as those used in this article.

Out of interest more than for scientific value, I considered adding this image of adenine from the Watson Crick model, with this caption. But then I looked on the Science Museum's flickr page from whence it came, and saw they labelled it as thymine despite the A (and the structure). This is obviously wrong, but I thought I'd mention it on here for discussion before I posted it. Assuming it is adenine, any ideas why the NH2 group at left seems asymmetrical? I presume this (and the long line at centre-left) are meant to show the hydrogen bond. Blythwood (talk) 23:39, 12 November 2015 (UTC)

Since no comment, uploading now. Blythwood (talk) 13:43, 14 November 2015 (UTC)

Assessment comment

The comment(s) below were originally left at Talk:Adenine/Comments, and are posted here for posterity. Following several discussions in past years, these subpages are now deprecated. The comments may be irrelevant or outdated; if so, please feel free to remove this section.

Changed rating to "high" as this is high school/SAT biology content. - tameeria 21:09, 18 February 2007 (UTC)

Last edited at 21:09, 18 February 2007 (UTC). Substituted at 06:42, 29 April 2016 (UTC)

Biosynthesis

I removed the following paragraph because its beginning repeated what was said in the previous paragraph, and the rest was not so much about adenine biosynthesis as about less specific ideas on the role of inosine monophosphate in relation to the other purines and carbon-based life in general. These ideas, if expressed more crisply, might be better as a part of the articles on Inosine monophosphate or Purine metabolismCharlesHBennett (talk) 19:11, 17 December 2019 (UTC)

"Both adenine and guanine are derived from the nucleotide inosine monophosphate (IMP), a class of molecular structures which have evolved into nucleic acids, the information half of the duality of functions of nucleic acids, the other half being the atomic-molecular elements which biochemically and molecular/cellular biology form the dynamic and chaotic life bearing process of organic carbon based life forms. IMP is the "template" molecular structure for nucleotides, thus the molecular structure of extant nucleic acids."