Polyoxypeptin isolated from Streptomyces: A bioactive cyclic depsipeptide containing the novel amino acid 3-hydroxy-3-methylproline

Kazuo Umezawa, Kumi Nakazawa, Toshio Uemura, Yoko Ikeda, Shinichi Kondo, Hiroshi Naganawa, Naoko Kinoshita, Hideki Hashizume, Masa Hamada, Tomio Takeuchi, Shigeru Ohba

Research output: Contribution to journalArticle

52 Citations (Scopus)

Abstract

Polyoxypeptin, a potent inducer of apoptosis in human pancreatic carcinoma cells, was isolated from an ethyl acetate extract of a Streptomyces culture broth. Structural determination by 2D-NMR and X-ray crystallographic analysis revealed that it is a novel cyclic hexadepsipeptide containing five hydroxylated amino acids. The unusual and hitherto unreported amino acid 3-hydroxy-3-methylproline was one of them.

Original languageEnglish
Pages (from-to)1389-1392
Number of pages4
JournalTetrahedron Letters
Volume39
Issue number11
DOIs
Publication statusPublished - 1998 Mar 12

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Depsipeptides
Streptomyces
Amino Acids
Cells
Nuclear magnetic resonance
X-Rays
Apoptosis
X rays
3-methylproline
Pancreatic Carcinoma
ethyl acetate

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Polyoxypeptin isolated from Streptomyces : A bioactive cyclic depsipeptide containing the novel amino acid 3-hydroxy-3-methylproline. / Umezawa, Kazuo; Nakazawa, Kumi; Uemura, Toshio; Ikeda, Yoko; Kondo, Shinichi; Naganawa, Hiroshi; Kinoshita, Naoko; Hashizume, Hideki; Hamada, Masa; Takeuchi, Tomio; Ohba, Shigeru.

In: Tetrahedron Letters, Vol. 39, No. 11, 12.03.1998, p. 1389-1392.

Research output: Contribution to journalArticle

Umezawa, K, Nakazawa, K, Uemura, T, Ikeda, Y, Kondo, S, Naganawa, H, Kinoshita, N, Hashizume, H, Hamada, M, Takeuchi, T & Ohba, S 1998, 'Polyoxypeptin isolated from Streptomyces: A bioactive cyclic depsipeptide containing the novel amino acid 3-hydroxy-3-methylproline', Tetrahedron Letters, vol. 39, no. 11, pp. 1389-1392. https://doi.org/10.1016/S0040-4039(98)00031-8
Umezawa, Kazuo ; Nakazawa, Kumi ; Uemura, Toshio ; Ikeda, Yoko ; Kondo, Shinichi ; Naganawa, Hiroshi ; Kinoshita, Naoko ; Hashizume, Hideki ; Hamada, Masa ; Takeuchi, Tomio ; Ohba, Shigeru. / Polyoxypeptin isolated from Streptomyces : A bioactive cyclic depsipeptide containing the novel amino acid 3-hydroxy-3-methylproline. In: Tetrahedron Letters. 1998 ; Vol. 39, No. 11. pp. 1389-1392.
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