Large-scale chemoenzymatic synthesis of blood group and tumor-associated poly- N-acetyllactosamine antigens

Poly- N-acetyllactosamines (pLNs) are common terminal sugars of many N- and O-linked glycan structures present in glycoproteins and glycolipids. Utilizing various glycosyltransferases, we developed new and efficient chemoenzymatic methods for the synthesis of pLNs in gram-scale. Specifically, the us...

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Bibliographic Details
Published in:Carbohydrate research 2006-07, Vol.341 (10), p.1447-1457
Main Authors: Vasiliu, Daniela, Razi, Nahid, Zhang, Yingning, Jacobsen, Nathan, Allin, Kirk, Liu, Xiaofei, Hoffmann, Julia, Bohorov, Ognian, Blixt, Ola
Format: Article
Language:English
Subjects:
Antigens, Neoplasm - biosynthesis
Blood group
Blood Group Antigens - biosynthesis
Chemoenzymatic synthesis
Fucosyltransferases - metabolism
Glycosyltransferases
Oligosaccharides
Poly- N-acetyllactosamines
Polysaccharides - biosynthesis
Polysaccharides - chemical synthesis
Sialyltransferases - metabolism
Tumor antigens
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Summary:Poly- N-acetyllactosamines (pLNs) are common terminal sugars of many N- and O-linked glycan structures present in glycoproteins and glycolipids. Utilizing various glycosyltransferases, we developed new and efficient chemoenzymatic methods for the synthesis of pLNs in gram-scale. Specifically, the use of sialyltransferases and fucosyltransferases enabled us to synthesize and purify 24 blood group and tumor-associated pLN derivatives with α-(2→3)- and α-(2→6)-linked sialic acid, as well as with α-(1→2)- and α-(1→3)-linked fucose. All synthesized derivatives were linked to a short 2-azidoethyl spacer for further modification.
ISSN:0008-6215
1873-426X
DOI:10.1016/j.carres.2006.03.043