Journal of the Chemical Society. Perkin transactions I p. 1749 - 1755 (1996)
Update date:2022-07-29
Topics:
Hitotsuyanagi, Yukio
Matsumoto, Yuji
Sasaki, Shin-Ichi
Suzuki, Jin
Takeya, Koichi
Yamaguchi, Kentaro
Itokawa, Hideji
RA-VII 1 was thionated with Davy reagent methyl 6 or Davy reagent p-tolyl 7 to afford novel thionopeptides, [Tyr-6-ψ(CS-NH)-D-Ala-1]RA-VII 8, [D-Ala-1-ψ(CS-NH)-Ala-2; Tyr-3-ψ(CS-NH)-Ala-4]RA-VII 9 and [Ala-2-ψ(CS-NH)-Tyr-3; Tyr-3-ψ(CS-NH)-Ala-4]RA-VII 10 in addition to known analogues [Tyr-3-ψ(CS-NH)-Ala-4]RA-VII 4 and [Tyr-3-ψ(CS-NH)-Ala-4; Tyr-6-ψ(CS-NH)-D-Ala-1]RA-VII 5. Thionopeptide 4 was reduced with nickel borohydride to give reduced peptide 11. An X-ray analysis and an NMR study revealed that compound 11 adopts a different conformation within the 18-membered-ring moiety from the predominant solution conformation of peptide 1 and of thionopeptides 4, 5, 8-10, which would explain the loss in activity of compound 11.
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