Specific, uncompetitive inhibition of beta-galactosidases by a 5,6-isopropylidenedioxyfuro[2,3-d]isoxazole-3-methanol derivative

C Schaller; R Demange; S Picasso; P Vogel

doi:10.1016/s0960-894x(98)00722-7

Specific, uncompetitive inhibition of beta-galactosidases by a 5,6-isopropylidenedioxyfuro[2,3-d]isoxazole-3-methanol derivative

Bioorg Med Chem Lett. 1999 Jan 18;9(2):277-8. doi: 10.1016/s0960-894x(98)00722-7.

Authors

C Schaller¹, R Demange, S Picasso, P Vogel

Affiliation

¹ Institut de chimie organique de l'Université de Lausanne, Lausanne-Dorigny, Switzerland.

PMID: 10021944
DOI: 10.1016/s0960-894x(98)00722-7

Abstract

(-)-(3aS,5S,6S.6aR)-3a,5,6,6a-Tetrahydro-5,6-isopropylide nedioxyfuro [2,3-d]isoxazole-3-methanol ((-)-5) has been tested toward 25 glycohydrolases and found to inhibit beta-galactosidase from Aspergillus niger (Ki = 18 microM) and that from Aspergillus orizae (Ki = 72 microM). Hydrolysis of the acetonide or exchange of CH2OH group for a CHO, CH2OMe or a CH2OMOM group suppresses the inhibitory activity.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Aspergillus / chemistry*
Dose-Response Relationship, Drug
Furans / pharmacology*
Hydrogen-Ion Concentration
Hydrolysis
Inhibitory Concentration 50
Isoxazoles / pharmacology*
Magnetic Resonance Spectroscopy
beta-Galactosidase / antagonists & inhibitors*

Substances

3a,5,6,6a-tetrahydro-5,6-isopropylidenedioxyfuro(2,3-d)isoxazole-3-methanol
Furans
Isoxazoles
beta-Galactosidase