Absolute stereochemistry of immunosuppressive macrolide brasilinolide A and its new congener brasilinolide C

Kazusei Komatsu; Masashi Tsuda; Yasushi Tanaka; Yuzuru Mikami; Jun'ichi Kobayashi

doi:10.1021/jo035773v

Absolute stereochemistry of immunosuppressive macrolide brasilinolide A and its new congener brasilinolide C

J Org Chem. 2004 Mar 5;69(5):1535-41. doi: 10.1021/jo035773v.

Authors

Kazusei Komatsu¹, Masashi Tsuda, Yasushi Tanaka, Yuzuru Mikami, Jun'ichi Kobayashi

Affiliation

¹ Graduate School of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan.

PMID: 14987008
DOI: 10.1021/jo035773v

Abstract

Brasilinolide A (2) is a 32-membered polyhydroxyl macrolide with immunosuppressive activity isolated from a pathogenic actinomycete, Nocardia brasiliensis IFM0406. The absolute configurations at 26 chiral centers of 2 and its new congener, brasilinolide C (1), were determined on the basis of the spectral data of 1 and degradation products derived from 1 and 2.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Carbohydrate Conformation
Hydrolysis
Immunosuppressive Agents / chemistry*
Immunosuppressive Agents / isolation & purification
Macrolides / chemistry*
Macrolides / isolation & purification
Magnetic Resonance Spectroscopy
Molecular Structure
Nocardia / metabolism*
Oxidation-Reduction
Pyrans / chemistry*
Pyrans / isolation & purification
Stereoisomerism

Substances

Immunosuppressive Agents
Macrolides
Pyrans
brasilinolide A
brasilinolide C