Synthesis of 3-deoxy-d-arabino-2-heptulosonic acid 7-phosphate by phosphorylation of methyl (methyl 3-deoxy-d-arabino-heptulopyranosid)onate

✍ Scribed by Mella Adlersberg; David B. Sprinson

• Publisher: Elsevier Science
• Year: 1984
• Tongue: English
• Weight: 418 KB
• Volume: 127
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(84)85101-0

✦ Synopsis

3-Deoxy-D-urubino-2-heptulosonic acid 7-phosphate (S), the first committed intermediate in aromatic amino acid biosynthesis, has been synthesized in good yield by treatment of methyl (methyl 3-deoxy-D-urubino-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-urubino-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.