A SIMPLE STRATEGY FOR CHANGING THE REGIOSELECTIVITY OF GLYCOSIDASE-CATALYSED FORMATION OF DISACCHARIDES: PART II, ENZYMIC SYNTHESIS in situ OF VARIOUS ACCEPTOR GLYCOSIDES

Article abstract of DOI:10.1016/0008-6215(88)80063-6

β-D-Galactosidase induced the formation of allyl, benzyl, and trimethylsilylethyl β-D-galactopyranosides on a 1-20-g scale from lactose and allyl alcohol, benzyl alcohol, and trimethylsilylethanol, respectively.Similarly, α-D-galactosidase catalysed the formation of allyl α-D-galactopyranoside from raffinose and allyl alcohol.The galactosides were used as acceptors for the preparation of the following disaccharide glycosides: β-D-Gal-(1->3)-β-D-Gal-OCH2CH=CH2, β-D-Gal-(1->6)-β-D-Gal-OCH2CH=CH2, β-D-Gal-(1->3)-β-D-Gal-OBn, β-D-Gal-(1->6)-β-D-Gal-OBn, β-D-Gal-(1->3)-β-D-Gal-OCH2CH2SiMe3, and α-D-Gal-(1->3)-α-D-Gal-OCH2CH=CH2.The β-D-galactosidase-catalysed reactions were efficient enough to allow the one pot preparation of the various β-linked mono- and digalactosides from lactose and alcohol.