Bulletin of the Chemical Society of Japan p. 2203 - 2210 (1984)
Update date:2022-08-17
Topics:
Shin
Otsuka
Triostin A, a cyclic octadepsipeptide, was synthesized with Z-D-Ser[Boc-Ala-MeCys(Bzl)-MeVal]-OH and Z-n-Ser[H-Ala-MeCys(Bzl)-MeVal]-OTce as key intermediates. The synthetic antibiotic was compared with natural triostin A in terms of chromatographic behaviors, NMR spectra, and antomicrobial activity to establish their identity. The NMR data on S,S'-dibenzyldihydrotriostin A showed that this intermediate lacking the disulfide linkage also existed as two conformers in chloroform. This observation excludes the possibility that the conformer equilibrium known to occur with triostin A is a consequence of the reversed chirality of the disulfide bond. Triostin A, a cyclic octadepsipeptide, was synthesized with Z-D-Ser left bracket Boc-Ala-MeCys(Bzl)-MeVal right bracket -OH and Z- D-Ser left bracket H-Ala-MeCys(Bzl)-MeVal right bracket -OTce as key intermediates. The synthetic antibiotic was compared with natural triostin A in terms of chromatographic behaviors, NMR spectra, and antimicrobial activity to establish their identity. The NMR data on S,S prime -dibenzyldihydrotriostin A showed that this intermediate lacking the disulfide linkage also existed as two conformers in chloroform. This observation excludes the possibility that the conformer equilibrium known to occur with triostin A is a consequence of the reversed chirality of the disulfide bond.
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