SYNTHESIS AND EVALUATION OF 1,5,6-TRIDEOXY-6,6-DIFLUORO-1,5-IMINO-D-GLUCITOL (1,6-DIDEOXY-6,6-DIFLUORONOJIRIMYCIN) AS A GLUCOSIDASE INHIBITOR

Authors
SZAREK MA WU XF SZAREK WA
Citation
Ma. Szarek et al., SYNTHESIS AND EVALUATION OF 1,5,6-TRIDEOXY-6,6-DIFLUORO-1,5-IMINO-D-GLUCITOL (1,6-DIDEOXY-6,6-DIFLUORONOJIRIMYCIN) AS A GLUCOSIDASE INHIBITOR, Carbohydrate research, 299(3), 1997, pp. 165-170
Citations number
14
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Carbohydrate research → ACNP
ISSN journal
00086215
Volume
299
Issue
3
Year of publication
1997
Pages
165 - 170
Database
ISI
SICI code
0008-6215(1997)299:3<165:SAEO1>2.0.ZU;2-7
Abstract
1,5,6-Trideoxy-6,6-difluoro-1,5-imino-D-glucitol hydrochloride (2) and 1,5,6-trideoxy-6,6-difluoro-1,5-imino-D-glucitol (3) have been synthe sized from L-sorbose. The formation of the C-5 difluoromethyl group wa s accomplished by difluorination of a carbonyl group by DAST. The resu lts of in vitro enzymic evaluation of 3 indicate that it is a competit ive inhibitor of yeast alpha-glucosidase (K-i = 7.5 mM) and a noncompe titive inhibitor of almond beta-glucosidase (K-i = 8.7 mM). (C) 1997 E lsevier Science Ltd.