Journal
TETRAHEDRON-ASYMMETRY
Volume 11, Issue 2, Pages 607-620Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0957-4166(99)00526-1
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5-Deoxy-5-fluoro-D-xylulose as well as a range of new 5,6-dimodifed open-chain analogues of D-fructose, namely the 5,6-diazido-5,6-dideoxy, 6-azido-5,6-dideoxy, 6-azido-5,6-dideoxy-5-fluoro, 5,6-dideoxy-5-fluoro, 5,6-dideoxy-6-fluoro and 5,6-dideoxy-5,6-difluoro derivatives, were synthesised employing glucose isomerase catalysed isomerisation of the corresponding D-xylo- and D-glucofuranoses as a key step. New compounds as well as some previously reported analogues such as 5-azido-5,6-dideoxy-6-fluoro-D- fructose were shown to be excellent substrates of polyol dehydrogenase from Burkholderia cepacia DSM 50181 with K-m values two orders of magnitude smaller than the corresponding natural substrates. (C) 2000 Elsevier Science Ltd, All rights reserved.
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