Polyprenyl phosphates: synthesis and structure-activity relationship for a biosynthetic system of Salmonella anatum O-specific polysaccharide.

Abstract:

:A series of polyprenyl phosphates with modified structure of polyprenyl residue was prepared through phosphorylation of polyprenyl trichloroacetimidates with phosphoric acid. Interaction of polyprenols with tetra-n-butylammonium dihydrogen phosphate and trichloroacetonitrile was found to represent a very efficient, simple and general method for the synthesis of polyprenyl phosphates. A procedure was developed for smooth conversion of polyprenyl pyrophosphates into the monophosphates through hydrolysis in the presence of 4-dimethylaminopyridine. The polyprenyl phosphates prepared were studied as substrates for the enzymes of Salmonella anatum O-specific polysaccharide biosynthesis. Correct stereochemistry of alpha- and beta-isoprenic units was found to be essential for substrate efficiency. At the more remote positions of the hydrocarbon chain just the presence of isoprenic units of any configuration seems necessary. Some changes in position of the phosphate group may be permissible without significant loss of substrate properties.

journal_name

Chem Phys Lipids

authors

Danilov LL,Druzhinina TN,Kalinchuk NA,Maltsev SD,Shibaev VN

doi

10.1016/0009-3084(89)90006-6

subject

Has Abstract

pub_date

1989-11-01 00:00:00

pages

191-203

issue

3-4

eissn

0009-3084

issn

1873-2941

pii

0009-3084(89)90006-6

journal_volume

51

pub_type

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