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Literature DB >> 8872127

One-pot enzymatic synthesis of the Gal alpha 1-->3Gal beta 1-->4GlcNAc sequence with in situ UDP-Gal regeneration.

C H Hokke¹, A Zervosen, L Elling, D H Joziasse, D H van den Eijnden.

Abstract

The trisaccharide Gal alpha 1-->3Gal beta 1-->4GlcNAc beta 1-->O-(CH2)8COOCH3 was enzymatically synthesized, with in situ UDP-Gal regeneration. By combination in one pot of only four enzymes, namely, sucrose synthase, UDP-Glc 4'-epimerase, UDP-Gal:GlcNAc beta 4-galactosyltransferase and UDP-Gal:Gal beta 1-->4GlcNAc alpha 3-galactosyltransferase, Gal alpha 1-->3Gal beta 1-->4GlcNAc beta 1-->O-(CH2)8COOCH3 was formed in a 2.2 mumol ml-1 yield starting from the acceptor GlcNAc beta 1-->O-(CH2)8COOCH3. This is an efficient and convenient method for the synthesis of the Gal alpha 1-->3Gal beta 1-->4GlcNAc epitope which pays an important role in various biological and immunological processes.

Entities: Chemical

Mesh：

Substances：

Year: 1996 PMID： 8872127 DOI： 10.1007/bf00731458

Source DB: PubMed Journal: Glycoconj J ISSN： 0282-0080 Impact factor: 2.916

17 in total

1. Alpha 1----3-galactosyltransferase: the use of recombinant enzyme for the synthesis of alpha-galactosylated glycoconjugates.

Authors: D H Joziasse; N L Shaper; L S Salyer; D H Van den Eijnden; A C van der Spoel; J H Shaper
Journal: Eur J Biochem Date: 1990-07-20

Review 2. Mac-2: a versatile galactose-binding protein of mammalian tissues.

Authors: R C Hughes
Journal: Glycobiology Date: 1994-02 Impact factor: 4.313

3. Role of carbohydrates in receptor-mediated fertilization in mammals.

Authors: P M Wassarman
Journal: Ciba Found Symp Date: 1989

4. Anti-pig IgM antibodies in human serum react predominantly with Gal(alpha 1-3)Gal epitopes.

Authors: M S Sandrin; H A Vaughan; P L Dabkowski; I F McKenzie
Journal: Proc Natl Acad Sci U S A Date: 1993-12-01 Impact factor: 11.205

5. Carbohydrate antigens of pig tissues reacting with human natural antibodies as potential targets for hyperacute vascular rejection in pig-to-man organ xenotransplantation.

Authors: R Oriol; Y Ye; E Koren; D K Cooper
Journal: Transplantation Date: 1993-12 Impact factor: 4.939

6. Stepwise transfer of alpha-D-Galp-(1-->3)-beta-D-Galp-(1-->4)-beta-D-GlcpNAc sequences to 3-OH and 6-OH of distal galactose residues in bi-, tri-, and tetra-antennary asialo-glycans of N-linked complex type.

Authors: J Helin; H Maaheimo; A Seppo; A Keane; O Renkonen
Journal: Carbohydr Res Date: 1995-01-17 Impact factor: 2.104

7. Enzymatic synthesis of the alpha 3-galactosyl-Lex tetrasaccharide: a potential ligand for selectin-type adhesion molecules.

Authors: D H Joziasse; W E Schiphorst; C A Koeleman; D H Van den Eijnden
Journal: Biochem Biophys Res Commun Date: 1993-07-15 Impact factor: 3.575

8. The Asn-linked carbohydrate chains of human Tamm-Horsfall glycoprotein of one male. Novel sulfated and novel N-acetylgalactosamine-containing N-linked carbohydrate chains.

Authors: K Hård; G Van Zadelhoff; P Moonen; J P Kamerling; F G Vliegenthart
Journal: Eur J Biochem Date: 1992-11-01

9. Gene sequences suggest inactivation of alpha-1,3-galactosyltransferase in catarrhines after the divergence of apes from monkeys.

Authors: U Galili; K Swanson
Journal: Proc Natl Acad Sci U S A Date: 1991-08-15 Impact factor: 11.205

10. Biosynthesis of bi-, tri-, and tetraantennary oligosaccharides containing alpha-D-galactosyl residues at their nonreducing termini. Branch specificity of the Ehrlich tumor cell alpha(1,3)-galactosyltransferase.

Authors: M J Elices; I J Goldstein
Journal: J Biol Chem Date: 1989-01-25 Impact factor: 5.157

12 in total

Review 1. Enzymatic synthesis of nucleotide sugars.

Authors: T Bülter; L Elling
Journal: Glycoconj J Date: 1999-02 Impact factor: 2.916

2. Donor substrate regeneration for efficient synthesis of globotetraose and isoglobotetraose.

Authors: Jun Shao; Jianbo Zhang; Przemyslaw Kowal; Peng George Wang
Journal: Appl Environ Microbiol Date: 2002-11 Impact factor: 4.792

Review 3. The yeast expression system for recombinant glycosyltransferases.

Authors: M Malissard; S Zeng; E G Berger
Journal: Glycoconj J Date: 1999-02 Impact factor: 2.916

4. UDP-N-Acetyl-alpha-D-glucosamine as acceptor substrate of beta-1,4-galactosyltransferase. Enzymatic synthesis of UDP-N-acetyllactosamine.

Authors: L Elling; A Zervosen; R G Gallego; V Nieder; M Malissard; E G Berger; J F Vliegenthart; J P Kamerling
Journal: Glycoconj J Date: 1999-07 Impact factor: 2.916