Carbohydrate research p. 119 - 129 (1986)
Update date:2022-08-05
Topics:
Legler
Pohl
A 12-step route is presented starting from 1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose for the preparation of the title compounds and their L-altro analogues. Their synthesis is based on the reduction with Raney nickel of a protected 5-hydroxyimino derivative of L-arabino-hexofuranos-5-ulose, with the following improvements for the preparation of a D-galactofuranose derivative: oxidation at C-3 with pyridinium dichromate-acetic anhydride, stereospecific reduction of a 3-O-acetyl-hex-3-enofuranose intermediate to the D-gulo derivative, and inversion at C-3 of its 3-tosylate with tetrabutylammonium acetate in chlorobenzene. alpha-D-Galactosidase from coffee beans and from Escherichia coli and beta-D-galactosidase from E. coli and Aspergillus wentii were inhibited with Ki values that ranged from 0.0007 to 8.2 microM. Formation of the enzyme-inhibitor complexes with the D-galactose analogue was on the time-scale of minutes, whereas the D-galactitol analogue showed a slow approach to the inhibition only with alpha-D-galactosidase from coffee beans and beta-D-galactosidase from A. wentii. N-Alkylation of the D-galactitol analogue was detrimental to the inhibition except for beta-D-galactosidase from E. coli and beta-D-glucosidase from almonds, but, even with these enzymes, the observed affinity enhancements were 10(2) to 10(3)-times smaller than those of N-alkylated D-galactosylamine and D-glucosylamine.
View MoreXinchang Jiu Xin Pharmaceutical Co., Ltd
website:http://www.jiuxinpharm.com
Contact:86 137 5756 8585
Address:Poyang industry Park
ABA Chemicals (Shanghai) Limited
Contact:021- 5115 9199-232
Address:Suite 18D, #201 Ningxia Road,
Jingzhou TianHe Sci&Tech Chemical Co., Ltd.
Contact:86-716-8331612
Address:Jiangjin Road, #18, High-grade technology industries development district, Jingzhou city, Hubei province
website:http://www.u-chemo.com
Contact:+86-21-61558312
Address:Dong Fang Road,
website:http://www.eastarchem.com/
Contact:1-800-898-2436
Address:1215 K Street, STE 1700
Doi:10.1016/S0040-4020(01)83463-3
(1987)Doi:10.1021/acs.orglett.1c01824
(2021)Doi:10.1039/c3ce26752k
(2013)Doi:10.1002/chem.200801277
(2008)Doi:10.1021/ja507530f
(2014)Doi:10.1021/jo00228a013
(1987)