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Synthesis and conformation of 5-thio-d-glucal, an inhibitor of glycosidases

✍ Scribed by Walter Korytnyk; Norman Angelino; Onda Dodson-Simmons; Michael Hanchak; Michael Madson; Stefica Valentekovic-Horvath

Publisher
Elsevier Science
Year
1983
Tongue
English
Weight
350 KB
Volume
113
Category
Article
ISSN
0008-6215

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✦ Synopsis

Molecules whose geometry resembles that of the transition state in enzymecatalyzed reactions are known to be excellent enzyme-inhibitors. Carbohydrate substrates of glycosidases are known to produce a carboxonium 1011 111 the transition state, the geometry of which probably resembles that of a tlattencd. half-chair

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## Abstract Sugar–iminosugar hybrid molecules made up of D‐glucose and D‐galactose with pyrrolidine‐based iminosugars, viz. 1,4‐dideoxy‐1,4‐imino‐L‐xylitol and 1,4‐dideoxy‐1,4‐imino‐L‐lyxitol, are synthesized from glycal epoxides and found to be moderate glycosidase inhibitors. (© Wiley‐VCH Verlag