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Glycobiology, 2002, Vol. 12, No. 7 409-420
© 2002 Oxford University Press

Molecular analysis of a novel family of complex glycoinositolphosphoryl ceramides from Cryptococcus neoformans: structural differences between encapsulated and acapsular yeast forms

Norton Heise2, Ana L.S. Gutierrez2, Katherine A. Mattos2, Christopher Jones3, Robin Wait4, José O. Previato2 and Lucia Mendonça-Previato1,2

2 Instituto de Biofísica Carlos Chagas Filho, Centro de Ciências da Saúde, Bloco G, Universidade Federal do Rio de Janeiro, 21944-970, Cidade Universitária, Ilha do Fundão, Rio de Janeiro, RJ, Brasil; 3 Laboratory for Molecular Structure, NIBSC, Herts EN6 3QG, UK; and 4 Kennedy Institute for Rheumatology Division, Faculty of Medicine, Imperial College of Science, Technology and Medicine, 1 Aspenlea Rd, London W6 8LH, UK

Complex glycoinositolphosphoryl ceramides (GIPCs) have been purified from a pathogenic encapsulated wild-type (WT) strain of Cryptococcus neoformans var. neoformans and from an acapsular mutant (Cap67). The structures of the GIPCs were determined by a combination of tandem mass spectrometry, nuclear magnetic resonance spectroscopy, methylation analysis, gas chromatography–mass spectrometry, and chemical degradation. The main GIPC from the WT strain had the structure Manp({alpha}1-3)[Xylp(ß1-2)] Manp({alpha}1-4)Galp(ß1-6)Manp({alpha}1-2)Ins-1-phosphoryl ceramide (GIPC A), whereas the compounds from the acapsular mutant were more heterogeneous in their glycan chains, and variants with Manp({alpha}1-6) (GIPC B), Manp({alpha}1-6) Manp({alpha}1-6) (GIPC C), and Manp({alpha}1-2)Manp({alpha}1-6)Manp({alpha}1-6) (GIPC D) substituents linked to the nonreducing terminal mannose residue found in the WT GIPC A were abundant. The ceramide moieties of C. neoformans GIPCs were composed of a C18 phytosphingosine long-chain base mainly N-acylated with 2-hydroxy-tetracosanoic acid in the WT GIPC while in the acapsular Cap67 mutant GIPCs, as well as 2-hydroxy-tetracosanoic acid, the unusual 2,3-dihydroxy-tetracosanoic acid was characterized. In addition, structural analysis revealed that the amount of GIPC in the WT cells was fourfold less of that in the acapsular mutant.

1 To whom correspondence should be addressed; E-mail: luciamp{at}biof.ufrj.br


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