Synthesis of 3-deoxy-d-arabino-2-heptulosonic acid 7-phosphate by phosphorylation of methyl (methyl 3-deoxy-d-arabino-heptulopyranosid)onate |
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Authors: | Mella Adlersberg David B Sprinson |
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Institution: | Department of Biochemistry, Columbia University College of Physicians and Surgeons, New York, New York 10032 U.S.A. |
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Abstract: | 3-Deoxy-d-arabino-2-heptulosonic acid 7-phosphate (5), the first committed intermediate in aromatic amino acid biosynthesis, has been synthesized in good yield by treatment of methyl (methyl 3-deoxy-d-arabino-2-heptulopyranosid)onate with diphenylphosphoric chloride under mild conditions to give the 7-diphenyl phosphate. Catalytic removal of the phenyl residues, followed by base-catalyzed hydrolysis resulted in formation of (methyl 3-deoxy-d-arabino-2-heptulopyranosid)onic acid dihydrogen 7-phosphate (4), which yielded a crystalline tris-(cyclohexylammonium) salt. Acid-catalyzed hydrolysis of 4 afforded 5, which was used to purify 3-dehydroquinate synthase. |
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Keywords: | Author to whom should it correspondence |
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