Total synthesis of caminoside B, a novel antimicrobial glycolipid isolated from the marine sponge Caminus sphaeroconia

Zaihong Zhang; Chengli Zong; Gaopeng Song; Guokai Lv; Yuexing Chun; Peng Wang; Ning Ding; Yingxia Li

doi:10.1016/j.carres.2010.01.015

Total synthesis of caminoside B, a novel antimicrobial glycolipid isolated from the marine sponge Caminus sphaeroconia

Carbohydr Res. 2010 Apr 19;345(6):750-60. doi: 10.1016/j.carres.2010.01.015. Epub 2010 Jan 29.

Authors

Zaihong Zhang¹, Chengli Zong, Gaopeng Song, Guokai Lv, Yuexing Chun, Peng Wang, Ning Ding, Yingxia Li

Affiliation

¹ School of Medicine and Pharmacy, Ocean University of China, Qingdao, China.

PMID: 20170905
DOI: 10.1016/j.carres.2010.01.015

Abstract

The first total synthesis of caminoside B, a novel marine antimicrobial glycolipid isolated from the marine sponge Caminus sphaeroconia, was developed. This marine small molecule inhibitor (IC(50)=20 microM) targeting type III secretory pathway of bacterial pathogenesis was assembled in good yield via a '2+2+1' strategy based on stereocontrolled construction of the four glycosidic linkages.

Publication types

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

MeSH terms

Animals
Anti-Infective Agents / chemical synthesis*
Anti-Infective Agents / chemistry*
Glycolipids / chemical synthesis*
Glycolipids / chemistry*
Magnetic Resonance Spectroscopy
Molecular Structure
Porifera / chemistry*

Substances

Anti-Infective Agents
Glycolipids
caminoside B