•  
  •  
 

Turkish Journal of Chemistry

DOI

10.3906/kim-1207-60

Abstract

Glycosides of 4-nitrocatechol (1,2-dihydroxy 4-nitrobenzene) with \alpha-D-glucopyranose and \alpha-D-mannopyranose were synthesized by the glycosylation of phenol with peracetylated sugars in the presence of BF_3\cdot OBu_2. The glycoside of 4-nitrocatechol with \beta-D-galactopyranose was prepared by the glycosylation of this phenol as sodium phenoxide with tetra-O-benzoyl-\alpha-D- galactopyranosyl bromide. The structure of the reaction products was confirmed by ^1 H and ^{13}C NMR spectra and by chemical analysis. The latter consisted of acidic hydrolysis, followed by ethyl ether extraction and colorimetric determination of 4-nitrocatechol in the ether phase and application of the anthrone method for the sugar in the water phase. The synthetic glycosides were tested as substrates for enzymes from animal, vegetal, and microbial materials.

First Page

299

Last Page

307

Included in

Chemistry Commons

Share

COinS