Amycolapeptins A and B, Cyclic Nonadepsipeptides Produced by Combined-culture of Amycolatopsis sp. and Tsukamurella pulmonis

J Org Chem. 2021 Jan 15;86(2):1843-1849. doi: 10.1021/acs.joc.0c02660. Epub 2021 Jan 7.

Abstract

Two nonapeptide natural products, amycolapeptins A (1) and B (2) with a 22-membered cyclic depsipeptide skeleton, β-hydroxytyrosine, and a highly modified side chain, which were not produced in a monoculture of the rare actinomycete Amycolatopsis sp. 26-4, were discovered in broth of its combined-culture with Tsukamurella pulmonis TP-B0596. The planar structures were elucidated by spectroscopic analyses (extensive 2D-NMR and MALDI-TOF MS/MS). The absolute configurations of component amino acids were unambiguously determined by the highly sensitive advanced Marfey's method we recently developed. Additionally, the structures of unstable/unusual moieties were corroborated by chemical synthesis and CD analysis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Actinobacteria*
  • Amycolatopsis
  • Molecular Structure
  • Peptides, Cyclic
  • Streptomyces*
  • Tandem Mass Spectrometry

Substances

  • Peptides, Cyclic

Supplementary concepts

  • Tsukamurella pulmonis