Onchidin: a cytotoxic depsipeptide with C2 symmetry from a marine mollusc

Tetrahedron Letters
1994.0

Abstract

Onchidin (I) is a cytotoxic depsipeptide isolated from the pulmonate mollusc Onchidium sp. Its structure is a cycle (MeVal-Amo-Val-Hiv-Hiv-MeVal-Amo-Val-Hiv-Hiv) made of two identical halves (C30H49N3O7, MeVal-Amo-Val-Hiv-Hiv). Onchidin contains a new β-amino acid: 3-amino-2-methylact-7-ynoic acid (Amo). It has C2-symmetry and this makes one half homotopic to the other so only signals for a "monomer" can be seen in the NMR spectra. The structure and absolute stereochemistry (all S) of onchidin was determined by extensive spectroscopic analysis, selective hydrolysis and chiral GCMS.

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