Characterization of the early stage aminoshikimate pathway in the formation of 3-amino-5-hydroxybenzoic acid: the RifN protein specifically converts kanosamine into kanosamine 6-phosphate

J Am Chem Soc. 2002 Sep 11;124(36):10644-5. doi: 10.1021/ja0206339.

Abstract

The biosynthesis of 3-amino-5-hydroxybenzoic acid (AHBA), precursor of the ansamycin and mitomycin antibiotics, proceeds by the aminoshikimate pathway from 3,4-dideoxy-4-amino-D-arabino-heptulosonic acid 7-phosphate (aminoDAHP). Identification of RifN, product of one of three genes from the rifamycin biosynthetic gene cluster known to be essential for aminoDAHP formation, as a specific kanosamine (3-deoxy-3-amino-D-glucose) 6-kinase establishes kanosamine and its 6-phosphate as specific intermediates in AHBA formation. This suggests a hypothetical reaction sequence for aminoDAHP formation, and thus for the early steps of AHBA biosynthesis, starting from UDP-D-glucose and introducing the nitrogen by oxidation and transamination at C-3.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Actinomycetales / genetics
  • Actinomycetales / metabolism
  • Aminobenzoates / metabolism*
  • Escherichia coli / genetics
  • Escherichia coli / metabolism
  • Glucosamine / metabolism*
  • Hydroxybenzoates
  • Organophosphates / metabolism
  • Recombinant Proteins / biosynthesis
  • Recombinant Proteins / genetics
  • Rifamycins / biosynthesis
  • Shikimic Acid / metabolism*
  • Sugar Acids / metabolism

Substances

  • 4-amino-3,4-dideoxyheptulosonic acid 7-phosphate
  • Aminobenzoates
  • Hydroxybenzoates
  • Organophosphates
  • Recombinant Proteins
  • Rifamycins
  • Sugar Acids
  • Shikimic Acid
  • kanosamine
  • 3-amino-5-hydroxybenzoic acid
  • Glucosamine