Kanosamine biosynthesis: A likely source of the aminoshikimate pathway's nitrogen atom

Jiantao Guo, J. W. Frost

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Abstract

The biosynthetic source of the nitrogen atom incorporated into the aminoshikimate pathway has remained a question for some time. 3-Amino-3-deoxy-d-fructose 6-phosphate has previously been demonstrated to be a precursor to 4-amino-3,4-dideoxy-d-arabino-heptulosonic acid 7-phosphate and 3-amino-5-hydroxybenzoic acid via the inferred intermediacy of 1-deoxy-1-imino-d-erythrose 4-phosphate in Amycolatopsis mediterranei cell-free extract. This investigation examines the possibility that the natural product kanosamine might be a precursor to 3-amino-3-deoxy-d-fructose 6-phosphate. Kanosamine 6-phosphate was synthesized by a chemoenzymatic route and incubated in A. mediterranei cell-free lysate along with d-ribose 5-phosphate and phosphoenolpyruvate. Formation of 4-amino-3,4-dideoxy-d-arabino-heptulosonic acid 7-phosphate and 3-amino-5-hydroxybenzoic acid was observed. Subsequent incubation in A. mediterranei cell-free lysate of glutamine and NAD with UDP-glucose resulted in the formation of kanosamine. The bioconversion of UDP-glucose into kanosamine along with the bioconversion of kanosamine 6-phosphate into 4-amino-3,4-dideoxy-d-arabino-heptulosonic acid 7-phosphate and 3-amino-5-hydroxybenzoic acid suggests that kanosamine biosynthesis is the source of the aminoshikimate pathway's nitrogen atom.

Original languageEnglish (US)
Pages (from-to)10642-10643
Number of pages2
JournalJournal of the American Chemical Society
Volume124
Issue number36
DOIs
StatePublished - Sep 11 2002

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ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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