Kanosamine biosynthesis: a likely source of the aminoshikimate pathway's nitrogen atom.
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.
Guo
Jiantao
J
Department of Chemistry, Michigan State University, East Lansing, MI 48824, USA.
Frost
John W
JW
D000192:Actinomycetales / Q000737:chemistry / Q000378:metabolism; D005944:Glucosamine / Q000096:biosynthesis*; D009584:Nitrogen / Q000378:metabolism*; D012765:Shikimic Acid / Q000378:metabolism*; D013400:Sugar Acids / Q000378:metabolism
C087302:4-amino-3,4-dideoxyheptulosonic acid 7-phosphate; D013400:Sugar Acids; D012765:Shikimic Acid; C014968:kanosamine; D005944:Glucosamine; D009584:Nitrogen