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Conformation‐Enabled Total Syntheses of Ohmyungsamycins A and B and Structural Revision of Ohmyungsamycin B
Author(s) -
Hur Joonseong,
Jang Jaebong,
Sim Jaehoon,
Son Woo Sung,
Ahn HeeChul,
Kim Tae Sung,
Shin YernHyerk,
Lim Changjin,
Lee Seungbeom,
An Hongchan,
Kim SeokHo,
Oh DongChan,
Jo EunKyeong,
Jang Jichan,
Lee Jeeyeon,
Suh YoungGer
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201711286
Subject(s) - stereochemistry , chemistry , total synthesis , amino acid , cyclic peptide , peptide , biochemistry
The first total syntheses of the bioactive cyclodepsipeptides ohmyungsamycin A and B are described. Key features of our synthesis include the concise preparation of a linear cyclization precursor that consists of N ‐methyl amides and non‐proteinogenic amino acids, and its macrolactamization from a bent conformation. The proposed structure of ohmyungsamycin B was revised based on its synthesis. The cyclic core of the ohmyungsamycins was shown to be responsible for the excellent antituberculosis activity, and ohmyungsamycin variants with truncated chains were evaluated for their biological activity.