Synthesis and utility of sulfated chromogenic carbohydrate model substrates for measuring activities of mucin-desulfating enzymes
| Autor: | Keith Clinch, Richard H. Furneaux, Phillippa L. Rhodes, Phillip M. Rendle, Gary B. Evans, Douglas Rosendale, Anthony M. Roberton, Damian P. Wright, Peter C. Tyler |
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| Rok vydání: | 2002 |
| Předmět: |
Aspergillus oryzae
Disaccharide Oligosaccharides Biochemistry Analytical Chemistry Bacteroides fragilis chemistry.chemical_compound Sulfation Monosaccharide chemistry.chemical_classification Molecular Structure biology Sulfates Chromogenic Sulfatase Organic Chemistry Mucin Mucins General Medicine biology.organism_classification carbohydrates (lipids) Enzyme Chromogenic Compounds Models Chemical chemistry Sulfatases |
| Zdroj: | Carbohydrate Research. 337:1095-1111 |
| ISSN: | 0008-6215 |
| Popis: | A chromogenic substrate, 4-nitrophenyl 2-acetamido-2-deoxy-β- d -glucopyranoside 6-sodium sulfate was synthesized and used in combination with β- 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 β- d -galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β- 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-β- d -glucopyranoside and giving an overall yield of 26.4%. The syntheses of 4-nitrophenyl β- d -galactopyranoside 3-triethylammonium sulfate and 6-triethylammonium sulfate and their use in combination with β-galactosidase as chromogenic substrates for detecting Bacteroides fragilis sulfatases with different specificities was also demonstrated. |
| Databáze: | OpenAIRE |
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