Synthesis of (+)-3,7,8-trideoxy-3,7-imino-D-threo-L-galacto-octitol and its inhibition of beta-glucosidases

The readily available 2,3:6,7-di-O-isopropylidene-D-glycero-D-gulo-heptono-1,4-lactone [(-)-5] was converted in four synthetic steps into the new iminooctitol (+)-3,7,8-trideoxy-3,7-imino-D-threo-L-galacto-octitol [(+)-10]. Although the piperidine unit of (+)-10 has the absolute configuration of beta-D-galacto-hexopyranosides, this iminoalditol does not inhibit five commercially available beta-galactosidases. However, (+)-10 was found to be a good competitive inhibitor of beta-glucosidases from almond (K-i = 15 mu M) and from Caldocellum saccharolyticum (K-i = 41 mu M).


Published in:
Carbohydrate Research, 281, 2, 277-284
Year:
1996
ISSN:
0008-6215
Keywords:
Note:
Univ lausanne,chim sect,bch,ch-1015 lausanne,switzerland.
Laboratories:




 Record created 2005-11-09, last modified 2018-03-17


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