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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
Further Information

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

    References

  • 1 Varki A. Glycobiology  1993,  3:  97 
    CrossrefPubMedGoogle Scholar
  • 2 Valette P. Pelenc V. Djouzi Z. Audrieux C. Paul F. Monsan P. Szylit O. J. Agr. Food Sci.  1993,  62:  121 
    Google Scholar
  • 3 Yanahira S. Morita M. Aoe S. Suguri T. Nakajima I. Deya E. J. Nutr. Sci. Vitaminol.  1995,  41:  83 
    Google Scholar
  • 4 Yanahira S. Morita M. Aoe S. Suguri T. Takada Y. Miura S. Nakajima I. J. Nutr. Sci. Vitaminol.  1997,  43:  123 
    Google Scholar
  • 5 Alles MS. Hartemink R. Meyboom S. Harryvan JL. Van Laere KM. Nagengart FM. Hautvast JG. Am. J. Clin. Nutr.  1999,  69:  980 
    Google Scholar
  • 6 Salminen S. Bouley C. Boutron-Ruault MC. Cummings JH. Franck A. Gibson GR. Isolauri E. Moreau MC. Br. J. Nutr.  1998,  80:  147 
    Google Scholar
  • 7 Gibson GR. Br. J. Nutr.  1998,  80:  209 
    Google Scholar
  • 8 Roberfroid MB. Br. J. Nutr.  1998,  80:  197 
    Google Scholar
  • 9 Fransen CTM. Van Laere KMJ. van Wijk AAC. Brüll LP. Dignum M. Thomas-Oates JE. Haverkamp J. Schols A. Voragen AGJ. Kamerling JP. Vliegenthart JFG. Carbohydr. Res.  1998,  314:  101 
    CrossrefGoogle Scholar
  • 10 Cote GL. Tao BY. Glycoconjugate J.  1990,  7:  145 
    CrossrefGoogle Scholar
  • 11 Murata T. Usui T. Biosci. Biotech. Biochem.  1997,  61:  1059 
    Google Scholar
  • 12 Kren V. Thiem J. Chem. Soc. Rev.  1997,  26:  463 
    CrossrefGoogle Scholar
  • 13 Yanahira S. Kobayashi T. Suguri T. Nakakoshi M. Miura S. Ishikawa H. Nakajima I. Biosci. Biotechol. Biochem.  1995,  59:  1021 
    Google Scholar
  • 14 Singh S. Scigelova M. Vic G. Crout DHG. J. Chem. Soc., Perkin Trans. 1  1996,  1921 
    CrossrefGoogle Scholar
  • 15 Usui T. Kubota S. Ohi H. Carbohydr. Res.  1993,  244:  315 
    Google Scholar
  • 16 Vetere A. Paoletti S. Biochem. Biophys. Res. Commun.  1996,  219:  6 
    CrossrefGoogle Scholar
  • 17 Sakai K. Katsumi R. Ohi H. Usui T. Ishido Y. J. Carbohydr. Chem.  1992,  11:  553 
    Google Scholar
  • 18 Herrmann GF. Ichikawa Y. Wandrey C. Gaeta FCA. Paulson JC. Wong C.-H. Tetrahedron Lett.  1993,  34:  3091 
    CrossrefGoogle Scholar
  • 19 Usui T. Morimoto V. Hayakawa Y. Kawaguchi M. Murata T. Matahira Y. Nishida Y. Carbohydr. Res.  1996,  285:  29 
    Google Scholar
  • 20 Kimura T. Takayama S. Huang H. Wong C.-W. Angew. Chem., Int. Ed. Engl.  1996,  35:  2348 
    Google Scholar
  • 21 Vic G. Hastings JJ. Howarth OW. Crout DHG. Tetrahedron: Asymmetry  1996,  7:  709 
    CrossrefGoogle Scholar
  • 22 Yanahira S. Yabe Y. Nakakoshi M. Miura S. Matsubara N. Ishikawa H. Biosci. Biotechnol. Biochem.  1998,  62:  1791 
    CrossrefGoogle Scholar
  • 23 Yanahira S. Kobayashi T. Suguri T. Nakakoshi M. Miura S. Ishikawa H. Nakajima I. Biosci. Biotechnol. Biochem.  1995,  59:  1021 
    Google Scholar
  • 24 Farkas E. Thiem J. Eur. J. Org. Chem.  1999,  3073 
    CrossrefGoogle Scholar