Synthetic applications of glucose isomerase: isomerisation of C-5-modified(2R,3R,4R)-configured hexoses into the corresponding 2-ketoses

Immobilised glucose isomerase (EC 5.3.1.5) accepted various (2R,3R,4R)-conf igured hexoses such as 5-deoxy-D-ribo-hexose, 5-azido-5-deoxy-D-allose, as well as the corresponding epimer at C-5, 5-azido-5-deoxy-L-talose, as subst rates. From the resulting azidodeoxyketoses, 5-azido-5-deoxy-D-psico- and - L-tagatopyranose, the powerful D-galactosidase inhibitors 2,5-dideoxy-2,5-i mino-D-galactital and -D-altritol were obtained in one additional step. (C) 1999 Elsevier Science Ltd. All rights reserved.