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Biological Chemistry

Editor-in-Chief: Brüne, Bernhard

Editorial Board: Buchner, Johannes / Lei, Ming / Ludwig, Stephan / Thomas, Douglas D. / Turk, Boris / Wittinghofer, Alfred

IMPACT FACTOR 2018: 3.014
5-year IMPACT FACTOR: 3.162

CiteScore 2018: 3.09

SCImago Journal Rank (SJR) 2018: 1.482
Source Normalized Impact per Paper (SNIP) 2018: 0.820

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Volume 382, Issue 2


Synthesis of Nucleotide-Activated Oligosaccharides by ?-Galactosidase from Bacillus circulans

Astrid Zervosen / Veronika Nieder / Ricardo Gutiérrez Gallego / Johannis P. Kamerling / Johannes F.G. Vliegenthart / Lothar Elling
Published Online: 2005-06-01 | DOI: https://doi.org/10.1515/BC.2001.037


The enzymatic access to nucleotideactivated oligosaccharides by a glycosidasecatalyzed transglycosylation reaction was explored. The nucleotide sugars UDPGlcNAc and UDPGlc were tested as acceptor substrates for ?galactosidase from Bacillus circulans using lactose as donor substrate. The UDPdisaccharides Gal(?1-4)GlcNAc(?1-UDP) (UDPLacNAc) and Gal(?1 4) Glc(?1-UDP) (UDPLac) and the UDPtrisaccharides Gal(?1-4)Gal(?1-4)GlcNAc(?1- UDP and Gal(?1 4 ) Gal(?1 4 ) Glc(?1-UDP) were formed stereo and regioselectively. Their chemical structures were characterized by [1]H and [13]C NMR spectroscopy and fast atom bombardment mass spectrometry. The synthesis in frozen solution at -5 C instead of 30 C gave significantly higher product yields with respect to the acceptor substrates. This was due to a remarkably higher product stability in the small liquid phase of the frozen reaction mixture. Under optimized conditions, at 5 C and pH 4.5 with 500 mM lactose and 100 mM UDPGlcNAc, an overall yield of 8.2% (81.8 mol, 62.8 mg with 100% purity) for Gal(b1 4 ) GlcNAc(?1-UDP) and 3.6% (36.1 mol, 35 mg with 96% purity) for Gal(?1-4)Gal(?1-4)GlcNAc(?1- UDP) was obtained. UDPGlc as acceptor gave an overall yield of 5.0% (41.3 mol, 32.3 mg with 93% purity) for Gal(?1-4)Glc(?1-UDP) and 1.6% (13.0 mol, 12.2 mg with 95% purity) for Gal(?1-4)Gal(?1- 4)Glc(?1-UDP). The analysis of other nucleotide sugars revealed UDPGal, UDPGalNAc, UDPXyl and dTDP, CDP, ADP and GDPGlc as further acceptor substrates for ?galactosidase from Bacillus circulans.

About the article

Published Online: 2005-06-01

Published in Print: 2001-02-12

Citation Information: Biological Chemistry, Volume 382, Issue 2, Pages 299–311, ISSN (Print) 1431-6730, DOI: https://doi.org/10.1515/BC.2001.037.

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