Journal article
Enzymatic synthesis of N-linked oligosaccharides terminating in multiple sialyl-Lewis(x) and GalNAc-Lewis(x) determinants: clustered glycosides for studying selectin interactions
Carbohydrate research, Vol.306(3), pp.387-400
01/1998
DOI: 10.1016/S0008-6215(97)10098-2
PMID: 9648247
Abstract
Galactosyltransferase, sialyltransferase, and fucosyltransferase were used to create a panel of complex oligosaccharides that possess multiple terminal sialyl-Le(x) (NeuAc alpha 2-3Gal[Fuc alpha 1-3] beta 1-4GlcNAc) and GalNAc-Le(x) (GalNAc[Fuc alpha 1-3]beta 1-4GlcNAc). The enzymatic synthesis of tyrosinamide biantennary, triantennary, and tetraantennary N-linked oligosaccharides bearing multiple terminal sialyl-Le(x) was accomplished on the 0.5 mumol scale and the purified products were characterized by electrospray MS and 1H NMR. Likewise, biantennary and triantennary tyrosinamide oligosaccharides bearing multiple terminal GalNAc-Le(x) determinants were synthesized and similarly characterized. The transfer kinetics of human milk alpha 3/4-fucosyltransferase were compared for biantennary oligosaccharide acceptor substrates possessing Gal beta 1-4GlcNAc, GalNAc beta 1-4GlcNAc, and NeuAc alpha 2-3Gal beta 1-4GlcNAc which established NeuAc alpha 2-3Gal beta 1-4GlcNAc as the most efficient acceptor substrate. The resulting complex oligosaccharides were chemically tethered through the tyrosinamide aglycone to the surface of liposomes containing phosphatidylthioethanol, resulting in the generation of glycoliposomes probe which will be useful to study relationships between binding affinity and the micro- and macro-clustering of selectin ligand.
Details
- Title: Subtitle
- Enzymatic synthesis of N-linked oligosaccharides terminating in multiple sialyl-Lewis(x) and GalNAc-Lewis(x) determinants: clustered glycosides for studying selectin interactions
- Creators
- V H Thomas - College of Pharmacy, University of Michigan, Ann Arbor 48109-1065, USAJ ElhalabiK G Rice
- Resource Type
- Journal article
- Publication Details
- Carbohydrate research, Vol.306(3), pp.387-400
- DOI
- 10.1016/S0008-6215(97)10098-2
- PMID
- 9648247
- NLM abbreviation
- Carbohydr Res
- ISSN
- 0008-6215
- eISSN
- 1873-426X
- Publisher
- Netherlands
- Grant note
- AI33189 / NIAID NIH HHS GM48049 / NIGMS NIH HHS
- Language
- English
- Date published
- 01/1998
- Academic Unit
- Pharmaceutical Sciences and Experimental Therapeutics; Craniofacial Anomalies Research Center; Medicinal and Natural Products Chemistry
- Record Identifier
- 9984065501002771
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