beta-turn mimetic: synthesis of cyclic thioenamino peptides

Organic Letters
Doron Pappo, Yoel Kashman

Abstract

[reaction: see text] Following the discovery of callynormine A, a marine metabolite of a new class, the cyclic endiamino peptides, and the synthesis of compounds of this group, we have now prepared an analogue group of compounds, i.e., cyclic thioenamine peptides. The latter peptides contain the alpha-amino-beta-thioacrylamide functionality, a potential new type of beta-turn mimic. The superiority of the SH group over the NH(2) group in the reaction with enol-tosylates was demonstrated.

References

Jun 21, 2002·Organic Letters·Bas WelsRob M J Liskamp
Feb 18, 2003·Journal of Peptide Science : an Official Publication of the European Peptide Society·Peter M Fischer
Dec 3, 2003·Chemical Communications : Chem Comm·Amy L KieranJeremy K M Sanders
Jul 17, 2004·Organic Letters·Nelly BererYoel Kashman
May 26, 2005·Journal of the American Chemical Society·Doron PappoYoel Kashman

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Citations

May 26, 2011·Journal of the American Chemical Society·Landon R WhitbyDale L Boger
Jul 11, 2018·Chemistry : a European Journal·Luis M De Leon RodriguezMargaret A Brimble
May 16, 2014·Chemical Communications : Chem Comm·Dong Jin LeeEun Jeong Yoo
Jul 23, 2014·Chemical Communications : Chem Comm·Roshna V NairGangadhar J Sanjayan
Sep 29, 2021·Chemical Communications : Chem Comm·Yuanyuan FuShenlin Huang

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