6R- and 6S-6C-Methylmannose from d-mannuronolactone. Inhibition of phosphoglucomutase and phosphomannomutase: agents for the study of the primary metabolism of mannose |
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| Institution: | 1. Dyson Perrins Laboratory, Oxford University, South Parks Road, Oxford OX1 3QY, UK;2. Biochemistry, Endocrinology and Metabolism Unit, Institute of Child Health, University of London, 30 Guilford Street, London WC1N 1EH, UK;3. Chemical Crystallography Laboratory, 9 Parks Road, Oxford OX1 3QU, UK;1. School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, People’s Republic of China;2. School of Chemistry, Sun Yat-sen University, Guangzhou 510275, People’s Republic of China;3. Department of Pharmaceutical Sciences, Oregon State University, Corvallis, OR 97331, USA;1. National Engineering Laboratory for Rice and By-products Further Processing, College of Food Science and Engineering, Central South University of Forestry & Technology, Changsha 410004, China;2. Institute of Medical Engineering and Translational Medicine, Tianjin University, Tianjin 300072, China;3. Technology Center of Changsha Customs, Hunan Academy of Inspection and Quarantine, Changsha 410004, China;4. Department of Pharmacy, University of South China, Henyang 421001, China;1. Junior Research Group for Microbial Biotechnology, Ruhr-University Bochum, 44780, Bochum, Germany;2. Department of Biosciences and Informatics, Keio University, 3-14-1 Hiyoshi, Yokohama, 223-8522, Japan;3. Institute of Molecular Biotechnology, Graz University of Technology, Petersgasse 14, 8010, Graz, Austria;1. College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou, 450052, China;2. Department of Chemical and Biomolecular Engineering, University of Notre Dame, Notre Dame, IN, 46556, United States;3. The Key Laboratory for Chemical Biology of Fujian Province, Xiamen University, Xiamen, 361005, China |
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| Abstract: | The syntheses of 6S-3 and 6R-6 6C-methylmannoses rely on opposite and highly stereoselective reductions of fully and partially protected ketones derived from d-mannuronolactone, respectively. Reduction of the silylated ketone 2 by sodium borohydride was accompanied by complete migration of the silyl protecting group to the new stereogenic centre; the silyl migration was suppressed when the reduction was conducted in the presence of cerium(III) chloride. Both epimers were good inhibitors of phosphoglucomutase and phosphomannomutase, and are specific inhibitors of phosphohexomutases. This work confirms that 6C-alkylhexoses provide a valuable set of compounds with good bioavailability for the study of enzymes involved in the primary metabolism of sugar phosphates. The X-ray crystallographic analysis of 7-deoxy-2,3:5,6-di-O-isopropylidene-α-l-glycero-d-manno-heptofuranose 16 is reported. |
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