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Synthesis and utility of sulfated chromogenic carbohydrate model substrates for measuring activities of mucin-desulfating enzymes.
- 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.
- Subjects :
- Aspergillus oryzae enzymology
Bacteroides fragilis enzymology
Chromogenic Compounds chemistry
Models, Chemical
Molecular Structure
Mucins chemistry
Oligosaccharides chemistry
Sulfates chemistry
Chromogenic Compounds chemical synthesis
Mucins metabolism
Oligosaccharides chemical synthesis
Sulfatases metabolism
Sulfates chemical synthesis
Subjects
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