Solution structure of polytheonamide B, a highly cytotoxic nonribosomal polypeptide from marine sponge

Toshiyuki Hamada, Shigeki Matsunaga, Masako Fujiwara, Kenichi Fujita, Hiroshi Hirota, Roland Schmucki, Peter Güntert, Nobuhiro Fusetani

研究成果: Article査読

54 被引用数 (Scopus)

抄録

Polytheonamide B (pTB), a highly cytotoxic polypeptide, is one of the most unusual nonribosomal peptides of sponge origin. pTB is a linear 48-residue peptide with alternating d-and l-amino acids and contains a total of eight types of nonproteinogenic amino acids. To investigate the mechanisms underlying its cytotoxic activity, we determined the three-dimensional structure of pTB by NMR spectroscopy, structure calculation, and energy minimization. pTB adopts a single right-handed β6.3-helical structure in a 1:1 mixture of methanol/chloroform with a length of approximately 45 Å and a hydrophilic pore of ca. 4 Å inner diameter. These features indicate that pTB molecules form transmembrane channels that permeate monovalent cations as gramicidin A channels do. The strong cytotoxicity of pTB can be ascribed to its ability to form single molecule channels through biological membranes.

本文言語English
ページ(範囲)12941-12945
ページ数5
ジャーナルJournal of the American Chemical Society
132
37
DOI
出版ステータスPublished - 2010 9 22

ASJC Scopus subject areas

  • 触媒
  • 化学 (全般)
  • 生化学
  • コロイド化学および表面化学

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