beta-turn mimetic: synthesis of cyclic thioenamino peptides.
[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.
Pappo
Doron
D
School of Chemistry, Tel-Aviv University, Ramat Aviv 69978, Israel.
Kashman
Yoel
Y
D000818:Animals; D018716:Molecular Mimicry; D015394:Molecular Structure; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry*; D011161:Porifera / Q000737:chemistry; D017433:Protein Structure, Secondary
D010456:Peptides, Cyclic; C495935:callynormine A