Relative stereochemistry determination and synthesis of the major chlorosulfolipid from Ochromonas danica

D Karl Bedke; Grant M Shibuya; Alban Pereira; William H Gerwick; Thomas H Haines; Christopher D Vanderwal

doi:10.1021/ja902138w

Relative stereochemistry determination and synthesis of the major chlorosulfolipid from Ochromonas danica

J Am Chem Soc. 2009 Jun 10;131(22):7570-2. doi: 10.1021/ja902138w.

Authors

D Karl Bedke¹, Grant M Shibuya, Alban Pereira, William H Gerwick, Thomas H Haines, Christopher D Vanderwal

Affiliation

¹ Department of Chemistry, University of California, Irvine, California 92697, USA.

PMID: 19445461
DOI: 10.1021/ja902138w

Abstract

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.

Publication types

Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Lipids / chemical synthesis
Lipids / chemistry*
Molecular Conformation
Nuclear Magnetic Resonance, Biomolecular
Ochromonas / chemistry*
Stereoisomerism

Substances

Lipids

Abstract

Publication types

MeSH terms

Substances

Grants and funding