Original scientific paper

2-Acetamido-2-deoxy-D-mannono-1,5-lactone: Synthesis and Inhibition of 2-Acetamido-2-deoxy-'B-D-glucosidase

M. Pokorny ; »Krka« Pharmaceutical and Chemical Works, 68000 Novo Mesto, Slovenia
N. Pravdić ; Department of Organic Chemistry and Biochemistry, »Ruder Boskovic« Institute, 41000 Zagreb, Croatia, Yugoslavia

Abstract

2-Acetamido-2-deoxy-n-mannono-1,5-lactone (I) was prepared
by mild hydrolysis of 2-acetamido-2-deoxy-4,6-0-isopropylidene-
n-mannono-1,5-lactone (IV).
The inhibitory activity of I and of the isomeric 1,4-lactone II,
as well as of 2-acetamido-2-deoxy-n-mannonic acid (III), was assayed
against 2-acetamido-2-deoxy-B-n-glucosidase from bull· epididymis.
The free acid III exhibits no inhibitory activity. The two
lactones act as competitive inhibitors against p-nitrophenyl 2-acetamido-
2-deoxy-B-n-glucopyranoside (inhibition constants Ki 33
· ~Lmol/dm3 and 8.3 mmol/dm3 for I and II, respectively), whereas
against p-nitrophenyl 2-acetamido-2-deoxy-B-D-galactopyranoside
only lactone I exhibits weak inhibitory activity (Ki, 9.3 mmol/dm3) .

Keywords

Hrčak ID:

196152

URI

https://hrcak.srce.hr/196152

Publication date:

26.4.1978.

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