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Synthesis 2003(5): 0699-0706
DOI: 10.1055/s-2003-38075
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Regioselective Synthesis of Galactosylated Tri- and Tetrasaccharides by Use of β-Galactosidase from Bacillus circulans

Erzsébet Farkasa, Ulja Schmidta, Joachim Thiem*a, Jörg Kowalczykb, Markwart Kunzb, Manfred Vogelb
a Institut für Organische Chemie, Universität Hamburg, Martin-Luther-King-Platz 6, 20146 Hamburg, Germany
Fax: +49(40)428384325; e-Mail: thiem@chemie.uni-hamburg.de;
b Südzucker AG, ZAFES, Wormser Straße 11, 67283 Obrigheim, Germany
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Publication History

Received 15 November 2002
Publication Date:
21 March 2003 (online)

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Abstract

β-Galactosidase from Bacillus circulans (EC 3.2.1.23) catalyses the transfer of galactose units to various glucose and galactose derivatives, forming β1→4 linkages. The synthesis of several biologically relevant tri- and tetrasaccharides {β-d-Galp-(1→4)-β-d-Galp-(1→4)-α,β-d-Glcp (2), β-d-Galp-(1→4)-α-d-Glcp-(1→4)-d-Glcp-ol/Manp-ol (4), β-d-Galp-(1→4)-α-d-Glcp-(1→6)-β-d-Fruf (6), β-d-Galp-(1→4)-α-d-Glcp-(1↔2)-β-d-Fruf (8), β-d-Galp-(1→4)-α-d-Glcp-(1↔2)-β-d-Fruf-(1↔2)-β-d-Fruf (10), β-d-Galp-(1→4)-α-d-Glcp-(1→6)-[α-d-Glcp-(1↔2)]-β-d-Fruf (12a), β-d-Galp-(1→4)-α-d-Glcp-(1↔2)-[α-d-Glcp-(1→6)]-β-d-Fruf (12b), α-d-Galp-(1→6)-[β-d-Galp-(1→4)]-α-d-Glcp-(1↔2)-β-d-Fruf (14a), β-d-Galp-(1→4)-α-d-Galp-(1→6)-α-d-Glcp-(1↔2)-β-d-Fruf (14b)} has been achieved in 11-59% yields by application of this enzyme.

Key words

transglycosylations - β-galactosidase - Bacillus circulans - enzymes - tri- and tetrasaccharides