Semisynthesis of an analogue of antitumor bicyclic hexapeptide RA-VII by fixing the Ala-2/Tyr-3 bond to Cis by incorporating a triazole cis-amide bond surrogate.
We prepared an analogue of an antitumor bicyclic hexapeptide RA-VII whose amide configuration between residues 2 and 3 was fixed to cis by incorporating a triazole cis-amide bond surrogate. This analogue was shown, by NMR studies, to take almost the same conformation as that of the minor conformer of RA-VII. It showed no cytotoxic activity.
Hitotsuyanagi
Yukio
Y
School of Pharmacy, Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan.
Motegi
Shuichi
S
Hasuda
Tomoyo
T
Takeya
Koichi
K
D000409:Alanine / Q000737:chemistry; D000577:Amides / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity; D010456:Peptides, Cyclic / Q000138:chemical synthesis / Q000737:chemistry / Q000633:toxicity; D014230:Triazoles / Q000737:chemistry*; D014443:Tyrosine / Q000737:chemistry
D000577:Amides; D000970:Antineoplastic Agents; D010456:Peptides, Cyclic; D014230:Triazoles; D014443:Tyrosine; C043548:RA VII; D000409:Alanine