Revised structure and structure-activity relationship of bisebromoamide and structure of norbisebromoamide from the marine cyanobacterium Lyngbya sp.

Hiroaki Sasaki, Toshiaki Teruya, Hidesuke Fukazawa, Kiyotake Suenaga

研究成果: Article査読

25 被引用数 (Scopus)

抄録

Novel potent cytotoxic peptides bisebromoamide (1) and norbisebromoamide (2) have been isolated from the marine cyanobacterium Lyngbya sp. The planar structure of these peptides was elucidated through the extensive application of 1D and 2D NMR techniques. The absolute stereostructure of 1 was determined by chemical degradation followed by chiral HPLC analysis. Recently, Tao and co-workers achieved synthesis of bisebromoamide, and the configuration of thiazoline moiety was revised. We re-investigated the stereochemistry of thiazoline moiety of 1. The structure-activity relationships of bisebromoamide (1) were investigated with the use of natural and synthetic analogs. Furthermore, bisebromoamide (1) potently inhibited protein kinase: the phosphorylation of ERK in NRK cells by PDGF-stimulation was selectively inhibited by treatment with 10-0.1 μM of 1.

本文言語English
ページ(範囲)990-994
ページ数5
ジャーナルTetrahedron
67
5
DOI
出版ステータスPublished - 2011 2月 4

ASJC Scopus subject areas

  • 生化学
  • 創薬
  • 有機化学

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