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Enzymatic transformations in supersaturated substrate solutions: II. Synthesis of disaccharides via transglycosylation
Author(s) -
MillqvistFureby Anna,
MacManus David A.,
Davies Stephen,
Vulfson Evgeny N.
Publication year - 1998
Publication title -
biotechnology and bioengineering
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.136
H-Index - 189
eISSN - 1097-0290
pISSN - 0006-3592
DOI - 10.1002/(sici)1097-0290(19981020)60:2<197::aid-bit7>3.0.co;2-i
Subject(s) - supersaturation , substrate (aquarium) , chemistry , enzyme , substrate specificity , stereochemistry , chromatography , chemical engineering , organic chemistry , biology , ecology , engineering
Enzymatic transglycosylation in supersaturated solutions of substrates was investigated using crude glycosidase preparations from barley, snail, and coffee beans. It was shown that the use of supersaturated glycoside solutions as media for transglycosylation reactions offers considerable advantages over conventional aqueous systems. These advantages include higher yields, more efficient use of the donor glycosides and improved volumetric productivity, especially in the case of poorly water‐soluble substrates. The regioselectivity of the glycosylation was not significantly affected by high concentrations of acceptor glycosides. It was also shown that the regioselectivity of transfer could be directed towards secondary hydroxyl groups by the use of methyl 6‐ O ‐acetyl‐α‐galactopyranoside as acceptor. The value of these approaches was demonstrated by the synthesis of methyl 3‐ and 4‐ O ‐β‐D‐galactopyranosyl‐α‐D‐galactopyranosides and methyl 3‐ O ‐β‐D‐galactopyranosyl‐α‐L‐fucopyranoside on a preparative scale. © 1998 John Wiley & Sons, Inc. Biotechnol Bioeng 60: 197–203, 1998.