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Chemoenzymatic Synthesis of 5‐Thio‐ D ‐xylopyranose
Author(s) -
Charmantray Franck,
Dellis Philippe,
Hélaine Virgil,
Samreth Soth,
Hecquet Laurence
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200600627
Subject(s) - ketose , thio , chemistry , aldolase a , synthon , transketolase , stereochemistry , stereospecificity , vetting , isomerization , glucose 6 phosphate isomerase , hydrogenolysis , enzyme , biochemistry , glycoside , aldose , catalysis , political science , law
5‐thio‐ D ‐xylopyranose, a synthon used for the preparation of drugs with antithrombotic activity, was synthesised by an enzymatic isomerisation from the corresponding ketose, 5‐thio‐ D ‐xylulofuranose, with glucose isomerase. This compound was obtained by two different chemoenzymatic routes, the key step being the stereospecific formation of a C–C bond, catalysed by transketolase or fructose‐1,6‐bisphosphate aldolase. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)