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Studies on Rubia Akane (RA) derivatives. Part 10. Backbone transformation of RA-VII, an antitumour cyclic hexapeptide, through thionation. X-ray crystal structure of [Tyr-3-ψ(CH2NH)-Ala-4]RA-VII

DOI: 10.1039/P19960001749

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 1749 - 1755 (1996)

Update date:2022-07-29

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Authors:

Hitotsuyanagi, YukioHitotsuyanagi, Yukio

Matsumoto, YujiMatsumoto, Yuji

Sasaki, Shin-IchiSasaki, Shin-Ichi

Suzuki, JinSuzuki, Jin

Takeya, KoichiTakeya, Koichi

Yamaguchi, KentaroYamaguchi, Kentaro

Itokawa, HidejiItokawa, Hideji

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Article abstract of DOI:10.1039/P19960001749

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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