Enzymatic synthesis of Ga1β1→3GlcNAc derivatives utilising a phosphorylase from Bifidobacterium bifidum 20082

Synlett

Volumn , Issue 5, 2000, Pages 728-730

  Farkas, Erzsébct ^a   Thiem, Joachim ^a   Krzewinski, Frédéric ^b   Bouquelet, Stéphane ^b  

^a UNIVERSITY OF HAMBURG   (Germany)

^b UNIVERSITÉ DES SCIENCES ET TECHNOLOGIES DE LILLE   (France)

Author keywords

Bifidobacterium bifidum; Carbohydrates; Enzymatic glycosylation; Gal 1 3GlcNAc; Phosphorylase

Indexed keywords

GALACTOSE; PHOSPHORYLASE;

ARTICLE; BIFIDOBACTERIUM BIFIDUM; CATALYSIS; CHEMICAL REACTION; ENZYME SYNTHESIS; GLYCOSYLATION; NONHUMAN; STEREOSPECIFICITY;

EID: 0034090494     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (31)

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25. α-D-Galp-1-P 5 and GlcpNAcαOoNP 4 were purchased from Sigma, Germany.
26. Enzymatic glycosylation procedure: General procedure A: α-D-Galp-1-P 5 as donor (24.2 mg, 0.072 mmol, 1.06 eq.) and the acceptors 1, 2, 3, or 4 (0.068 mmol, 1 eq.) were incubated in imidazole buffer (27 mL, 25 mM, pH 6.8) with the partially purified phosphorylase (3 mL) at 37 °C for 20 h. Then, the reaction was terminated by heating to 90 °C for 10 min. Separation of the products from the starting materials was achieved by column chromatography (Biogel P2). The products 6, 8, and 10 were dissolved in pyridine (1 mL), acetic anhydride (1 mL) added, and the reaction mixture was stirred at room temperature for 12 h. After work-up the residue was dried in vacuo, then co-evaporated with toluene, concentrated and purified by silica gel chromatography (dichloromethane-acetone, 85: 15) to yield compounds 7, 9, and 11 in 25, 30 and 14% yields, respectively.
27. General procedure B: α-D-Galp-1-P 5 as donor (41 mg, 0.123 mmol, 1.0 eq.) and the acceptor 1 and 2 (0.15 mmol, 1.2 eq.) were incubated in imidazole buffer (24 mL, 25 mM, pH 6.8) with the partially purified phosphorylase (6 mL) at 37 °C for 48 h. The reaction was terminated by heating to 90 °C for 10 min. The separation of the products from the starting materials was achieved by column chromatography (Biogel P2). The products 6 and 8 were dissolved in pyridine (1 mL), acetic anhydride (1 mL) added, and the reaction mixture was stirred at room temperature for 12 h and dried in vacuo. The residue was co-evaporated with toluene, concentrated and purified by column chromatography (dichloromethane-acetone, 85: 15) to yield compounds 7 and 9 in 49 and 57% yields respectively.
28. 11N (397.38).
29. 3′,′= 3.1
30. 17N (649.60).
31. Physical and spectroscopic data of compounds 8, 9, 10 and 11 proved to be identical with those published by Gambert, U.; Gonzalez Lio, R.; Farkas, E.; Thiem, J.; Bencomo, V.V.; Lipták, A. Bioorg. Med. Chem. 1997, 5, 1285-1291.