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.
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.
Arakawa
Kenji
K
Department of Chemistry, Box 351700, University of Washington, Seattle, WA 98195-1700, USA.
Müller
Rolf
R
Mahmud
Taifo
T
Yu
Tin-Wein
TW
Floss
Heinz G
HG
D000192:Actinomycetales / Q000235:genetics / Q000378:metabolism; D062365:Aminobenzoates / Q000378:metabolism*; D004926:Escherichia coli / Q000235:genetics / Q000378:metabolism; D005944:Glucosamine / Q000378:metabolism*; D062385:Hydroxybenzoates; D010755:Organophosphates / Q000378:metabolism; D011994:Recombinant Proteins / Q000096:biosynthesis / Q000235:genetics; D012294:Rifamycins / Q000096:biosynthesis; D012765:Shikimic Acid / Q000378:metabolism*; D013400:Sugar Acids / Q000378:metabolism
C087302:4-amino-3,4-dideoxyheptulosonic acid 7-phosphate; D062365:Aminobenzoates; D062385:Hydroxybenzoates; D010755:Organophosphates; D011994:Recombinant Proteins; D012294:Rifamycins; D013400:Sugar Acids; D012765:Shikimic Acid; C014968:kanosamine; C031509:3-amino-5-hydroxybenzoic acid; D005944:Glucosamine