Glycobiology Advance Access originally published online on September 26, 2003
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Glycobiology vol 14 no 1 pp. 1-12, 2004
© Oxford University Press 2004; all rights reserved.
Default biosynthesis pathway for blood group–related glycolipids in human small intestine as defined by structural identification of linear and branched glycosylceramides in a group O Le(a-b-) nonsecretor
2 Institute of Medical Biochemistry and 3 Swegene Proteomics Center, Göteborg University, Box 440, SE 405 30, Sweden; and 4 Glycoscience Research Centre, Auckland University of Technology, Private Bag 92006, Auckland 1020, New Zealand, and Kiwi Ingenuity Limited, P.O. Box 39373, Howick, New Zealand
Received on March 4, 2003; revised on August 31, 2003; accepted on September 3, 2003
Glycoconjugates of the GI tract are important for microbial interactions. The expression of histo-blood group glycosyltransferases governs both the expression of blood group determinants and in part the structure and size of the glycoconjugates. Using neutral glycolipids isolated from the small intestine of a rare blood group O Le(a-b-) ABH secretor-negative (nonsecretor) individual we were able to map the "default" pathway of the individual lacking ABO, Lewis, and secretor glycosyltransferases. Structures were deduced with combined analysis of mass spectrometry (MALDI-TOF and ESI-MS/MS), and 1H NMR (500 and 600 MHz). All structures present at a level >5% were structurally resolved and included two extended structures: Galß4(Fuc
3)GlcNAcß3(Galß4[Fuc3]GlcNAcß6)Galß4GlcNAcß3Galß4Glcß1Cer and Galß3GlcNAcß3(Galß4[Fuc3]GlcNAcß6)Galß3GlcNAcß3Galß4Glcß1Cer. The first, a novel component, is based on a type 2 chain and bears the Lex glycotopes on both its branches. The second, a major component, is based on a type 1 chain, which bears a 3-linked type 1 precursor (Lec) glycotope and a 6-linked Lex glycotope on its branches. This latter structure is identical to that previously isolated from plasma and characterized by MS and GC-MS but not by NMR. Structural resolution of these structures was supported by reanalysis of the blood group H–active decaosylceramides previously isolated from rat small intestine. Other minor linear monofucosylated penta-, hepta-, and difucosylated octaosylceramides, some bearing blood group determinants, were also identified. The cumulative data were used to define a default biosynthesis pathway where it can be seen that carbohydrate chain extension, in the absence of blood group glycosyltransferases, is controlled and regulated by non–blood group fucosylation and branching with type 2 Galß4GlcNAc branches.
1 To whom correspondence should be addressed; e-mail: kiwi{at}aut.ac.nz
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