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Synthesis of disaccharide derivatives employing β-N-acetyl- d-hexosaminidase, β-d-galactosidase and β-d-glucuronidase

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Abstract

β-N-Acetyl-d-hexosaminidase from Aspergillus oryzae catalysed the stereo- and regiospecific formation of the 6-O-benzylated disaccharide derivatives GalNAcβ1-3(6- OBn)Galβ-SEt and GlcNAcβ1-3(6-OBn)Galβ-SEt, which were obtained in transglycosylation reactions employing ethyl 6- O-benzyl-1-thio-β-d-galactopyranoside as acceptor. Preparative amounts of the chitobiose derivative GlcNAcβ1- 3GlcNAcβ-OPhNO2-p was prepared as well. β- N-Acetyl-d-hexosaminidase from bovine testes catalysed the specific synthesis of GlcNAcβ1-3(6-OBn)GlcNH2β-SEt and GalNAcβ1-3(6-OBn)GlcNH2β-SEt, employing ethyl 2-amino-6-O-benzyl-2-deoxy-1-thio-β-d-glucopyranoside as acceptor. β-d-Glucuronidase from E. coli was found to catalyse the formation of GlcAβ1-3(6-OBn)GlcNH2β- SEt employing the same acceptor.

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Nilsson, K.G., Eliasson, A., Pan, H. et al. Synthesis of disaccharide derivatives employing β-N-acetyl- d-hexosaminidase, β-d-galactosidase and β-d-glucuronidase. Biotechnology Letters 21, 11–15 (1999). https://doi.org/10.1023/A:1005439302682

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  • DOI: https://doi.org/10.1023/A:1005439302682

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