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Talk:Thioester

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The links to footnote 12 seem to be corrupt... (A pity - this is very interesting stuff - tf@dpmms.cam.ac.uk) — Preceding unsigned comment added by 222.154.72.253 (talk) 01:58, 18 August 2020 (UTC)[reply]

Does is stike anyone else that de Duve's explanation is not satisfactory? Keep in mind that the use of ATP involves several steps of enzyme catalysations(if that's a word). How would thioester be useful without such enzymes, and does it need them at all, or can it self-hydrolysize? --Alkafett 20:26, 18 Apr 2005 (UTC)

Using IUPAC nomenclature - esters are named alcohol then carboxylic acid (classically) - which would make R-S-(C=0)-R (discussed in this article) a thiolester not a thioester. Thionoester is the correct term for an R-O-(C=S)-R species - deriving its name from thione functional group ( C=S ).

I know I have seen examples in the literature (chemical and biochemical) with both thioester and thiolester being used to mean R-S-(C=0)-R - so I can understand the confusion. but i feel that this article should be alterred for clarification ----arthuc01 5.27 7th Jan 2007 (GMT)

I'm not the greatest chemistry buff, but can't a sulfhydryl containing molecule be derivatized to a thioester using an activated acyl group also? Jordanboutilier (talk) 05:29, 1 February 2008 (UTC)[reply]

A thioester, if it stably exists, is obviously matching self-dehydration to self-hydrolysis. But in de Duve's scenario for a pre-ATP energy economy, as well as with coenzyme A's need to hang onto a fatty acid, then release it, one must wonder how a single thiol can have its nucleophilicity switched on demand between two values, flipping the equilibrium as circumstances require. I have long thought that pantetheine's amides were spaced advantageously for an intramolecular charge-relay system. Merely by rotating a few of its bonds - with near-zero net free-energy change - the molecule could show a great range of pKa at the thiol. Some years ago I sought to test this by substituting simple acyl or sulfonyl moieties for the pantoyl group in pantetheine to see if the thiol's acidity responded. Since I was a lousy chemist, I never got pure products, and so confirmed nothing. Thus I believe this does not violate Wikipedia's rule against original research! Meanwhile, an online search for "pantetheine charge-relay" yields nothing germane. Clearly, though, pantetheine has some special aptitude for its office. Jahutter (talk) 22:48, 2 August 2012 (UTC)[reply]

Today I excised this part because they appear to be very specialized and barely on topic: The C-H groups adjacent to the [[carbonyl]] in thioesters are mildly acidic (more so than in esters<ref>{{Cite journal |last1=Bew |first1=S. P. |last2=Stephenson |first2=G. R. |last3=Rouden |first3=J. |last4=Martinez-Lozano |first4=L.A. |last5=Seylani |first5=H. |title=Malonic Acid Half Oxyesters and Thioesters: Solvent-Free Synthesis and DFT Analysis of Their Enols |journal=Org. Lett. |year=2013 |volume=15 |pages=3805–3807 |doi=10.1021/ol400804b |issue=15}}</ref><ref>{{Cite journal |last1=Bordwell |first1=F. G. |last2=Fried |first2=H. E. |title=Heterocyclic Aromatic Anions with 4''n'' + 2 pi-Electrons |journal=J. Org. Chem. |year=1991 |volume=56 |pages=4218–4223 |doi=10.1021/jo00013a027 |issue=13}}</ref>) and undergo [[aldol condensation]]s. This kind of reaction occurs in the biosynthesis of fatty acids.--Smokefoot (talk) 14:46, 5 July 2017 (UTC)[reply]