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| Content Provider | World Health Organization (WHO)-Global Index Medicus |
|---|---|
| Author | Morrison, James P. Schoenhofen, Ian C. Tanner, Martin E. |
| Description | Author Affiliation: Morrison JP ( Department of Chemistry, University of British Columbia, Vancouver, BC, Canada V6T 1Z1.) |
| Abstract | UDP-N-acetylglucosamine 5-inverting 4,6-dehydratase (PseB) is a unique sugar nucleotide dehydratase that inverts the C-5'' stereocentre during conversion of UDP-N-acetylglucosamine to UDP-2-acetamido-2,6-dideoxy-beta-l-arabino-hexos-4-ulose. PseB catalyzes the first step in the biosynthesis of pseudaminic acid, which is found as a post-translational modification on the flagellin of Campylobacter jejuni and Helicobacter pylori. PseB is proposed to use its tightly bound NADP+ to oxidize UDP-GlcNAc at C-4'', enabling dehydration. The alpha,beta unsaturated ketone intermediate is then reduced by delivery of the hydride to C-6'' and a proton to C-5''. Consistent with this, PseB from C. jejuni has been found to incorporate deuterium into the C-5'' position of product during catalysis in D2O. Likewise, PseB catalyzes solvent isotope exchange into the H-5'' position of product, and eliminates HF from the alternate substrate, UDP-6-deoxy-6-fluoro-GlcNAc. Mutants of the putative catalytic residues aspartate 126, lysine 127 and tyrosine 135 have severely compromised dehydratase, solvent isotope exchange, and HF elimination activities. |
| File Format | HTM / HTML |
| ISSN | 00452068 |
| Issue Number | 6 |
| Volume Number | 36 |
| e-ISSN | 10902120 |
| Journal | Bioorganic Chemistry |
| Language | English |
| Publisher | Elsevier |
| Publisher Date | 2008-12-01 |
| Publisher Place | United States |
| Access Restriction | One Nation One Subscription (ONOS) |
| Subject Keyword | Discipline Biochemistry Hydro-lyases Chemistry Sugar Acids Uridine Diphosphate N-acetylglucosamine Aspartic Acid Campylobacter Jejuni Metabolism Catalysis Helicobacter Pylori Chemical Synthesis Ketones Lysine Mutagenesis, Site-directed Mutation Oxygen Solvents Tyrosine Water Journal Article Research Support, Non-u.s. Gov't |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry Drug Discovery Molecular Biology Biochemistry |
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