Inhibitory effect of diglucosylamines on two β-glucosidases

✍ Scribed by N. Kolarova; R. Trgiňa; K. Linek; V. Farkaš

• Book ID: 102991654
• Publisher: Elsevier Science
• Year: 1995
• Tongue: English
• Weight: 199 KB
• Volume: 273
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(95)00105-3

✦ Synopsis

Glycosylamines are compounds of interest for the enzymology of carbohydrates due to their ability to act as competitive inhibitors for glycosidases [1,2]. They usually bind more tightly with the enzymes than their neutral counterparts, provided that the basic character of their nitrogen atom is not diminished [2]. A main drawback of glycosylamines, however, is their tendency to hydrolyze [3]. Diglycosylamines may be expected to be more stable than glycosylamines because the combined electron-withdrawing effect of the two-ring oxygens may decrease the basicity of the glycosylamine nitrogen. This paper deals with an investigation of the utility of diglucosylamines as inhibitors for fl-glycosidases from Trichoderma reesei and from sweet almonds.

Two anomers of diglucosylamine, namely ot-o-glucopyranosyl-fl-o-glucopyranosylamine (1) and di-/3-D-glucopyranosylamine (2) besides the N-acetylated derivative of (2) were tested as inhibitors of fl-glucosidases.