An Ichip-Domesticated Sponge Bacterium Produces an N-Acyltyrosine Bearing an α-Methyl Substituent

Org Lett. 2019 Oct 4;21(19):7768-7771. doi: 10.1021/acs.orglett.9b02710. Epub 2019 Sep 16.

Abstract

The ichip (isolation chip) was employed for the first time in a marine sponge (Xestospongia muta), and a putatively new bacterial species, Alteromonas sp. RKMC-009, was isolated. Strain RKMC-009 produces a novel N-acyltyrosine (1) that is appended with a rare α-methyl substituent within the aminoacyl moiety and also exhibits Gram-positive antibacterial activity. We determined through an SAR experiment that the α-methyl is necessary for Staphylococcus activity of 1 and that it enhances Enterococcus activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alteromonas / chemistry*
  • Animals
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification
  • Anti-Bacterial Agents / pharmacology*
  • Bacterial Proteins / chemistry
  • Bacterial Proteins / isolation & purification
  • Bacterial Proteins / pharmacology*
  • Enterococcus / drug effects*
  • Microbial Sensitivity Tests
  • Molecular Conformation
  • Porifera
  • Staphylococcus / drug effects*

Substances

  • Anti-Bacterial Agents
  • Bacterial Proteins