Relative Stereochemistry Determination and Synthesis of the Major Chlorosulfolipid from Ochromonas danica

被引：70

作者：

Bedke, D. Karl ^{[1
]}

Shibuya, Grant M. ^{[1
]}

Pereira, Alban ^{[2
]}

Gerwick, William H. ^{[2
]}

Haines, Thomas H. ^{[3
]}

Vanderwal, Christopher D. ^{[1
]}

机构：

[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA

[2] Univ Calif San Diego, Scripps Inst Oceanog, Ctr Marine Biotechnol & Biomed, La Jolla, CA 92093 USA

[3] Rockefeller Univ, Dept Biochem & Mol Biol, New York, NY 10021 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2009年 / 131卷 / 22期

关键词：

HETERONUCLEAR COUPLING-CONSTANTS; ADRIATIC MUSSELS; NMR EXPERIMENTS; BIOSYNTHESIS; ESTERS; CHLORINATION; SHELLFISH; MOTIFS; TOXINS; LIPIDS;

D O I：

10.1021/ja902138w

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The relative stereochemistry of the major chlorosulfolipid of the chrysophyte alga Ochromonas danica, to which we have given the name "danicalipin A", is reported. The first synthesis of this lipid, via several stereospecific electrophilic additions to alkenes, serves to corroborate the stereochemical assignment made by NMR spectroscopy. The synthesis strategy described should be applicable to other chlorosulfolipids and should provide access to sufficient material for studies of the lipid's properties and function in membranes.

引用

页码：7570 / +

页数：4

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