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Glycobiology Advance Access published online on March 16, 2007
Glycobiology, doi:10.1093/glycob/cwm030
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© The Author 2007. Published by Oxford University Press. All rights reserved. For permissions, please e-mail: journals.permissions@oxfordjournals.org

Communications

Characterization of glycoinositolphosphoryl ceramide structure mutant strains of Cryptococcus neoformans

Ana L.S. Gutierrez2, Layla Farage2, Manuel N. Melo2, Ronaldo S. Mohana-Borges2, Yann Guerardel3, Bernadete Coddeville3, Jean-Michel Wieruszeski3, Lucia Mendonça-Previato1,2 and Jose O. Previato2

2 Instituto de Biofísica Carlos Chagas Filho, Universidade Federal do Rio de Janeiro Cidade Universitária, 21944979, Rio de Janeiro, Brasil
3 Unité de Glycobiologie Structurale et Fonctionnelle, Université des Sciences et Technologies de Lille, 59655 Villeneuve D'Ascq, France

1 To whom correspondence should be addressed; Tel: +55 21 2562 6646; Fax: +55 21 2280 8193; E-mail: luciamp{at}biof.ufrj.br

Received on February 16, 2007; revised on March 7, 2007; accepted on March 11, 2007

In fungi, glycoinositolphosphoryl ceramide biosynthetic pathway produces essential molecules for growth, viability and virulence. In previous studies, we demonstrated that the opportunistic fungus Cryptococcus neoformans synthesizes a complex family of xylose branched glycoinositolphosphoryl ceramides, all of which have not been previously reported in fungi. As an effort to understand the biosynthesis of these sphingolipids, we have now characterized the structures of glycoinositolphosphoryl ceramides from C. neoformans wild type (KN99{alpha}) and mutant strains that lack UDP-Xylose, by disruption of either UDP-Glucose dehydrogenase (NE321) or UDP-Glucuronic acid decarboxylase (NE178). The structures of glycoinositolphosphoryl ceramides were determined by a combination of nuclear magnetic resonance spectroscopy, tandem mass spectrometry and gas chromatography-mass spectrometry. The main and largest glycoinositolphosphoryl ceramide from wild type strain was identified as {alpha}-Manp(1->6){alpha}-Manp(1->3){alpha}-Manp[ß-Xylp(1->2)]{alpha}-Manp(1->4)J-Galp(1->6){alpha}-Manp(1->2)Ins-1-P-Ceramide, whereas the most abundant glycoinositolphosphoryl ceramide from both mutant strains was found to be {alpha}-Manp(1->3){alpha}-Manp(1->4)ß-Galp(1->6){alpha}-Manp(1->2)Ins-1-P-Ceramide. The ceramide moieties of C. neoformans wild type and mutant strains were composed of a C18 phytosphingosine, which was N-acylated with 2-hydroxy tetra-, or hexacosanoic acid, and 2,3-dihydroxy-tetracosanoic acid. Our structural analysis results indicate that the C. neoformans mutant strains are unable to complete the assembly of the glycoinositolphosphoryl ceramide-oligosaccharide moiety due the absence of xylose side-chain.

Key words: Cryptococcus neoformans / Cryptococcusmutants / glycoinositolphosphoryl ceramide / mass spectrometry / NMR spectroscopy / UDP-Xylose


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