Synthesis and characterization of new chromogenic substrates for exoglycosidases: \alpha-glucosidase, \alpha-mannosidase, and \beta-galactosidase

Authors

DUMITRU PETRU IGA
RICHARD SCHMIDT
SILVIA IGA
CORINA LOREDANA HOTOLEANU
FLORENTINA DUICA
ALINA NICOLESCU
SILVIA STEFANIA GITMAN

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.

Keywords

Glycosylation, 4-nitrocatechol-glycoside, exoglycosidase, enzymatic substrate

First Page

299

Last Page

307

Recommended Citation

IGA, DUMITRU PETRU; SCHMIDT, RICHARD; IGA, SILVIA; HOTOLEANU, CORINA LOREDANA; DUICA, FLORENTINA; NICOLESCU, ALINA; and GITMAN, SILVIA STEFANIA (2013) "Synthesis and characterization of new chromogenic substrates for exoglycosidases: \alpha-glucosidase, \alpha-mannosidase, and \beta-galactosidase," Turkish Journal of Chemistry: Vol. 37: No. 2, Article 13. https://doi.org/10.3906/kim-1207-60
Available at: https://journals.tubitak.gov.tr/chem/vol37/iss2/13