Micromonosporamide A with Glutamine-Dependent Cytotoxicity from Micromonospora sp. MM609M-173N6: Isolation, Stereochemical Determination, and Synthesis

  • Org Lett. 2021 Oct 15;23(20):7981-7985. doi: 10.1021/acs.orglett.1c02974.
Toshifumi Takeuchi  1 ,  Masaki Hatano  1 ,  Hideyuki Muramatsu  1 ,  Yumiko Kubota  1 ,  Ryuichi Sawa  1 ,  Masayuki Igarashi  1
Affiliations
  • 1. Institute of Microbial Chemistry (BIKAKEN), 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021, Japan.
PMID: 34585936 DOI: 10.1021/acs.orglett.1c02974
Abstract

An acyldipeptide, micromonosporamide A, was isolated from the fermentation broth of Micromonospora sp. MM609M-173N6 by bioassay-guided fractionation using a glutamine compensation assay. The planar structure was elucidated on the basis of comprehensive one- and two-dimensional nuclear magnetic resonance and high-resolution mass spectrometry. The relative and absolute configuration of the entire molecule were determined using a combined approach, involving chromatographic analysis by liquid chromatography-mass spectrometry, advanced Marfey's method, and total synthesis. Micromonosporamide A exhibited glutamine-dependent antiproliferative activity.

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