Absolute configuration of TPU-0043, a pentaene macrolide from Streptomyces sp

Yasuhiro Igarashi; Yasuko In; Toshimasa Ishida; Tsuyoshi Fujita; Takashi Yamakawa; Hiroyasu Onaka; Tamotsu Furumai

doi:10.1038/ja.2005.71

Absolute configuration of TPU-0043, a pentaene macrolide from Streptomyces sp

J Antibiot (Tokyo). 2005 Aug;58(8):523-5. doi: 10.1038/ja.2005.71.

Authors

Yasuhiro Igarashi¹, Yasuko In, Toshimasa Ishida, Tsuyoshi Fujita, Takashi Yamakawa, Hiroyasu Onaka, Tamotsu Furumai

Affiliation

¹ Biotechnology Research Center, Toyama Prefectural University, 5180 Kurokawa, Kosugi, Toyama 939-0398, Japan. [email protected]

PMID: 16266125
DOI: 10.1038/ja.2005.71

Abstract

An antifungal pentaene macrolide TPU-0043 was isolated from Streptomyces sp. TP-A0625. The absolute configuration of TPU-0043 was determined to be 2R-(n-butyl)-16-methyl-3S,5S,7S,9R,11R,13R,15S,26S, 27R-nonahydroxyoctacosa-16,18,20,22,24-pentaenoic acid, 27-lactone, by X-ray crystallography of its 13-p-bromobenzenesulfonyl derivative.

MeSH terms

Antifungal Agents / chemistry*
Antifungal Agents / isolation & purification
Macrolides / chemistry*
Macrolides / isolation & purification
Macrolides / pharmacology
Magnetic Resonance Spectroscopy
Polyamines
Streptomyces / chemistry*

Substances

2R-(n-butyl)-16-methyl-3S,5S,7S,9R,11R,13R,15S,26S, 27R-nonahydroxyoctacosa-16,18,20,22,24-pentaenoic acid, 27-lactone
Antifungal Agents
Macrolides
Polyamines