title: Probing the Role of N-Acetyl-glutamyl 5-Phosphate, an Acyl Phosphate, in the Construction of the Azabicycle Moiety of the Azinomycins.
abstract: The azinomycins are potent antitumor agents produced by the soil bacterium Streptomyces sahachiroi and contain a novel aziridino[1,2-a]pyrrolidine core; its synthesis involves at least 14 steps. This study reports the first reconstitution of N-acetylglutamine semialdehyde formation by two enzymes encoded in the azinomycin biosynthetic gene cluster. The reaction proceeds through the formation of an acylphosphate and establishes N-acetyl-glutamyl 5-phosphate and N-acetylglutamine semialdehyde as intermediates in the complex biosynthesis of the aziridino[1,2-a]pyrrolidine moiety.
authors.forename: Keshav K
authors.initials: KK
authors.lastname: Nepal
authors.forename: Rachel P
authors.initials: RP
authors.lastname: Lee
authors.forename: Yohannes H
authors.initials: YH
authors.lastname: Rezenom
authors.forename: Coran M H
authors.initials: CM
authors.lastname: Watanabe
mesh_terms: D000970:Antineoplastic Agents / Q000378:metabolism; D053961:Azabicyclo Compounds; D001426:Bacterial Proteins / Q000737:chemistry / Q000502:physiology; D053898:Biosynthetic Pathways; D020134:Catalytic Domain; D004151:Dipeptides; D005971:Glutamates / Q000378:metabolism*; D006020:Glycopeptides / Q000096:biosynthesis; D036341:Intercellular Signaling Peptides and Proteins; D007700:Kinetics; D009281:Naphthalenes / Q000378:metabolism; D010455:Peptides / Q000378:metabolism; D013302:Streptomyces / Q000201:enzymology / Q000235:genetics
chemical_list: D000970:Antineoplastic Agents; D053961:Azabicyclo Compounds; D001426:Bacterial Proteins; D004151:Dipeptides; D005971:Glutamates; D006020:Glycopeptides; D036341:Intercellular Signaling Peptides and Proteins; D009281:Naphthalenes; D010455:Peptides; C051055:azinomycin B; C051054:azinomycin A