A unique chemoenzymatic synthesis of α-galactosyl epitope derivatives containing free amino groups

Efficient separation and further manipulation

Jianwen Fang, Xi Chen, Wei Zhang, Jianqiang Wang, Peter R. Andreana, Peng George Wang

Research output: Contribution to journalArticle

28 Citations (Scopus)

Abstract

A novel chemoenzymatic approach for the synthesis of oligosaccharides containing free amino groups has been developed in which thermophilic glycosidases and a fusion enzyme containing catalytic domains of uridine-5'- diphospho-galactose 4-epimerase and α(1→3) galactosyltransferase were used. This methodology, in conjunction with a convenient purification procedure employing ion exchange chromatography, facilitates the lengthy and high-cost process of carbohydrate synthesis. The prepared oligosaccharides range from disaccharide lactosamine (1a), trisaccharide α-Gal-(1→3)-β-Gal-(1→4)- GlcNH2 (2), tetrasaccharide β-Gal-(1→4)-β-GlcNH2-(1→3)-β-Gal-(1→4)- β-Glc-N3 (7), to pentasaccharide α-Gal-(1→3)-β-Gal-(1→4)-β-GlcNH2- (1→3)-β-Gal-(1→4)-b-Glc-N3 (15). Compounds 2 and 15 are derivatives of natural α-Gal epitopes. Both of them have shown comparable activities with their natural parent compounds toward human anti-Gal IgG. This method provides a practical approach for the preparation and purification of oligosaccharides containing free amino groups, which can be further derivatized for the enhancement of biological activities.

Original languageEnglish (US)
Pages (from-to)4089-4094
Number of pages6
JournalJournal of Organic Chemistry
Volume64
Issue number11
DOIs
StatePublished - May 28 1999
Externally publishedYes

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Oligosaccharides
Epitopes
Derivatives
Purification
Galactosyltransferases
Racemases and Epimerases
Trisaccharides
Disaccharides
Glycoside Hydrolases
Uridine
Chromatography
Bioactivity
Galactose
Ion exchange
Fusion reactions
Immunoglobulin G
Carbohydrates
Enzymes
Costs

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

A unique chemoenzymatic synthesis of α-galactosyl epitope derivatives containing free amino groups : Efficient separation and further manipulation. / Fang, Jianwen; Chen, Xi; Zhang, Wei; Wang, Jianqiang; Andreana, Peter R.; Wang, Peng George.

In: Journal of Organic Chemistry, Vol. 64, No. 11, 28.05.1999, p. 4089-4094.

Research output: Contribution to journalArticle

Fang, Jianwen ; Chen, Xi ; Zhang, Wei ; Wang, Jianqiang ; Andreana, Peter R. ; Wang, Peng George. / A unique chemoenzymatic synthesis of α-galactosyl epitope derivatives containing free amino groups : Efficient separation and further manipulation. In: Journal of Organic Chemistry. 1999 ; Vol. 64, No. 11. pp. 4089-4094.
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