The total synthesis of 2-O-arachidonoyl-1-O-stearoyl-sn-glycero-3-phosphocholine-1,3,1'-(13)C3 and -2,1'-(13)C2 by a novel chemoenzymatic method.

Abstract:

:2-O-Arachidonoyl-1-O-stearoyl-sn-glycero-3-phosphocholine was synthesized with carbon-13 enrichment of the three glycerol carbons and the carbonyl of the stearoyl group. Phospholipase A(2) was utilized to give optically pure lyso-PC, and only 3% acyl migration occurred during reacylation with arachidonic acid anhydride. This phospholipid is an important biosynthetic precursor of arachidonic acid metabolites as well as the endocannabinoid 2-arachidonoylglycerol (2-AG), and is now available for NMR studies.

journal_name

Chem Phys Lipids

authors

Duclos RI Jr

doi

10.1016/j.chemphyslip.2009.08.001

subject

Has Abstract

pub_date

2010-01-01 00:00:00

pages

102-9

issue

1

eissn

0009-3084

issn

1873-2941

pii

S0009-3084(09)00309-0

journal_volume

163

pub_type

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