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Glycobiology Advance Access originally published online on March 12, 2009
Glycobiology 2009 19(7):715-725; doi:10.1093/glycob/cwp039
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© The Author 2009. Published by Oxford University Press. All rights reserved. For permissions, please e-mail: journals.permissions@oxfordjournals.org

The CMP-legionaminic acid pathway in Campylobacter: Biosynthesis involving novel GDP-linked precursors

Ian C Schoenhofen1, Evgeny Vinogradov, Dennis M Whitfield, Jean-Robert Brisson and Susan M Logan

Institute for Biological Sciences, National Research Council, Ottawa, Ontario, K1A 0R6 Canada

1 To whom correspondence should be addressed: Tel: +1-613-991-2141; Fax: +1-613-952-9092; e-mail: ian.schoenhofen{at}nrc-cnrc.gc.ca

Received on December 18, 2008; revised on February 17, 2009; accepted on March 7, 2009

The sialic acid-like sugar 5,7-diacetamido-3,5,7,9-tetradeoxy-D-glycero-D-galacto-nonulosonic acid, or legion- aminic acid, is found as a virulence-associated cell-surface glycoconjugate in the Gram-negative bacteria Legionella pneumophila and Campylobacter coli. L. pneumophila serogroup 1 strains, causative agents of Legionnaire's disease, contain an {alpha}2,4-linked homopolymer of legionaminic acid within their lipopolysaccharide O-chains, whereas the gastrointestinal pathogen C. coli modifies its flagellin with this monosaccharide via O-linkage. In this work, we have purified and biochemically characterized 11 candidate biosynthetic enzymes from Campylobacter jejuni, thereby fully reconstituting the biosynthesis of legionaminic acid and its CMP-activated form, starting from fructose-6-P. This pathway involves unique GDP-linked intermediates, likely providing a cellular mechanism for differentiating between this and similar UDP-linked pathways, such as UDP-2,4-diacetamido-bacillosamine biosynthesis involved in N-linked protein glycosylation. Importantly, these findings provide a facile method for efficient large-scale synthesis of legionaminic acid, and since legionaminic acid and sialic acid share the same D-glycero-D-galacto absolute configuration, this sugar may now be evaluated for its potential as a sialic acid mimic.

Key words: Campylobacter jejuni / flagellin glycosylation / legionaminic acid / neuraminic acid / sialic acid


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