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Synthesis and utility of sulfated chromogenic carbohydrate model substrates for measuring activities of mucin-desulfating enzymes.

Authors :
Clinch K
Evans GB
Furneaux RH
Rendle PM
Rhodes PL
Roberton AM
Rosendale DI
Tyler PC
Wright DP
Source :
Carbohydrate research [Carbohydr Res] 2002 Jun 12; Vol. 337 (12), pp. 1095-111.
Publication Year :
2002

Abstract

A chromogenic substrate, 4-nitrophenyl 2-acetamido-2-deoxy-beta-D-glucopyranoside 6-sodium sulfate was synthesized and used in combination with beta-N-acetylhexosaminidase for detection of the sulfatase, MdsA, by release of 4-nitrophenol. MdsA was originally isolated from the bacterium Prevotella strain RS2 and is believed to be involved in desulfation of sulfomucins, major components of the mucus barrier protecting the human colon surface. The exo nature of the MdsA sulfatase was indicated by its inability to de-esterify the disaccharide 4-nitrophenyl beta-D-galactopyranosyl-(1-->4)-2-acetamido-2-deoxy-beta-D-glucopyranoside 6-sodium sulfate. This latter compound was prepared from monosaccharide precursors by two different methods, the shorter requiring just six steps from 4-nitrophenyl 2-acetamido-2-deoxy-beta-D-glucopyranoside and giving an overall yield of 26.4%. The syntheses of 4-nitrophenyl beta-D-galactopyranoside 3-triethylammonium sulfate and 6-triethylammonium sulfate and their use in combination with beta-galactosidase as chromogenic substrates for detecting Bacteroides fragilis sulfatases with different specificities was also demonstrated.

Details

Language :
English
ISSN :
0008-6215
Volume :
337
Issue :
12
Database :
MEDLINE
Journal :
Carbohydrate research
Publication Type :
Academic Journal
Accession number :
12062525
Full Text :
https://doi.org/10.1016/s0008-6215(02)00104-0