Talk:Dithiothreitol

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Wiki Education Foundation-supported course assignment

This article was the subject of a Wiki Education Foundation-supported course assignment, between 14 January 2020 and 7 May 2020. Further details are available on the course page. Student editor(s): Onievesl. Peer reviewers: Alexfutia, Crendonb.

Above undated message substituted from Template:Dashboard.wikiedu.org assignment by PrimeBOT (talk) 19:37, 16 January 2022 (UTC)[reply]

Reducing agent?

DTT is not actually a reducing reagent. The oxidation numbers of the sulfer atoms involved in the disulfide exchange remain constant at -1. It should be more properly stated that it attacks disulfide bonds as a nucleophile.

The vast majority of the chemistry world disagrees with you. In a disulfide, you have 4 lone electron pairs on the two sulfurs, plus the 1 pair in the bond, for a total of 10 electrons (ignoring bonding to the rest of the molecule). In the two free thiols case, you still have the 4 lone pairs, plus 2 pairs in each of the bonds to hydrogen, for a total of 12 electrons. (The hydrogens come in as H+ ions, and don't bring electrons with them.) Change in electron number absolutely implies redox chemistry. As "reduction describes the gain of an electron by a molecule, atom or ion", and since the disulfide gained electrons, it has been reduced by the action of DTT. Thus DTT is a "reducing agent", by definition. -- Tmhand 19:29, 6 July 2006 (UTC)[reply]

One should read the rules for determining oxidation numbers before posting. In a thiol attached to a carbon the oxidation number of the sulfur is always -II whereas in a disulfide it is always -I. So the reaction from two thiols to a disulfide is clearly an oxidation which absolutely justifies it being a reducing agend. Every person that has truly some understanding of chemistry will agree with this. --129.98.60.199 19:02, 17 May 2007 (UTC)[reply]

Stereochemistry

On the image, the DTT is 2R-3R at the beginning and at the final, it is 2S-3R, please change the image! Talk about L-DTT and D-DTT. Usually DTT is a DL-DTT racemic mixture, but it is important to do the difference.—Preceding unsigned comment added by 132.204.84.95 (talk • contribs)

Please correct the stereochemistry! In the structure you show the 2S-3S form, but name it 2R-3R; on the other hand the shown reaction starts from 2S-3R, which is DTE, not DTT, and arrives to 2R-3R DTT. 193.6.29.254 13:42, 11 June 2007 (UTC)Bagoston[reply]

I have commented out the image so that it is not visible, until it can be corrected/replaced. Also I have changed the infobox so that the IUPAC name matches the structure. Interestingly, at the link to the Pubchem page for this compound, the same error is there - the image and IUPAC name don't match in terms of stereochemistry. Finally, I agree that some mention of the sterechemical issues should be made in the article. I'll try to get to it soon, if someone else doesn't get to it first. --Ed (Edgar181) 14:05, 11 June 2007 (UTC)[reply]

missing figures

Fig 2 is missing. Sal7777777 14:24, 13 June 2007 (UTC)[reply]

This image was removed because it was incorrect. I have now recreated it without the errors and replaced it. --Ed (Edgar181) 15:09, 13 June 2007 (UTC)[reply]

WikiProject class rating

This article was automatically assessed because at least one WikiProject had rated the article as start, and the rating on other projects was brought up to start class. BetacommandBot 07:52, 10 November 2007 (UTC)[reply]

Possible error in reducing agent section

"The reducing power of DTT is limited to pH values below 7, since only the negatively charged thiolate form -S– is reactive (the protonated thiol form -SH is not); the pKa of the thiol groups is 9.2 and 10.1."

Shouldn't that be above 7 then (basic solution)? Adding acid would only favor the thiol form. July 2014

Copyright violation?

The entire section on "properties" and parts of other sections have identical wording to this page: https://www.usbio.net/technicalSheet.php?item=D8070

There are also other pages with identical text, most of them from suppliers of DTT, like the URL in the last paragraph. Either they are copying Wikipedia, or they are all getting the same text from the original manufacturer and copying it to their websites.

Who copied who? I'm not sure. 130.95.203.172 (talk) 01:01, 18 February 2015 (UTC)[reply]

Earwig's points to few sources:

https://osm.bio/Editor is clearly a copy of an older version of our article.
https://www.interchim.fr/ft/0/054721.pdf file is dated 2020, but earlier version might have existed, and it does not look like a copy of our text. The oldest version of the file on arhive.org is dated 2008 ([1])
https://agscientific.com/blog/dithiothreitol-aka-clelands-reagent.html is a blog entry dated 2017. The bulk of our text is dated c. 2007, so there appears to be no issue here
https://www.researchgate.net/topic/Dithiothreitol is a Q&A session dated 2017-2021, so these are most likely quotes from our article
https://agscientific.com/products/biochemicals/reducing-agents/dithiothreitol-dtt-5-g.html is a brand new page, so there is no direct issue

So, if not for #2, concerns are minor. However, #2 might be an indicator of existence of much older sources. Викидим (talk) 21:25, 12 November 2024 (UTC)[reply]

Pinging early contributors @WillowW, Chaiken, MoreTruthier, and Taekyubabo: who might remember the details of the old days. Викидим (talk) 21:35, 12 November 2024 (UTC)[reply]

Assessment comment

The comment(s) below were originally left at Talk:Dithiothreitol/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.

great article which should be high priority given that many novices will arrive here for a variety of reasons.

a few suggestions for what may be worth adding (?):

link to pages on biological regulation of redox potential in various compartments

it's excellent that you suggest TCEP as DTT alternative, perhaps links to and 1 sentence summaries of other candidate reducing agents that could be useful under various circumstances such as sodium dithionite ...

link to detailed chemistry of sulfur containing amino acids - ie what are potential reduction and oxidation products that can be derived from cysteine side chain.

Sek25 04:19, 13 August 2007 (UTC)[reply]

Last edited at 04:19, 13 August 2007 (UTC). Substituted at 13:31, 29 April 2016 (UTC)