title: 7-Deazapurine biosynthesis: NMR study of toyocamycin biosynthesis in Streptomyces rimosus using 2-13C-7-15N-adenine.
abstract: Although 7-deazapurines are well known and feature in the hypermodified RNA base queuosine, and in a range of nucleoside antibiotics such as toyocamycin, a mechanistic understanding of their biosynthesis is a longstanding problem. In particular, the obligatory loss of the N-7 nitrogen atom is puzzling, and in order to address this mechanistic conundrum a novel doubly labeled purine, [2-(13)C, 7-(15)N]-adenine, has been prepared and used as a biosynthetic precursor to toyocamycin in Streptomyces rimosus. NMR spectroscopy and mass spectrometry clearly showed incorporation of (13)C but loss of (15)N in the toyocamycin produced.
authors.affiliation: School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD, UK.
authors.forename: Ugo
authors.initials: U
authors.lastname: Battaglia
authors.forename: Jed E
authors.initials: JE
authors.lastname: Long
authors.forename: Mark S
authors.initials: MS
authors.lastname: Searle
authors.forename: Christopher J
authors.initials: CJ
authors.lastname: Moody
mesh_terms: D000225:Adenine / Q000737:chemistry* / Q000378:metabolism; D002247:Carbon Isotopes; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D009587:Nitrogen Isotopes; D011687:Purines / Q000096:biosynthesis / Q000737:chemistry*; D013302:Streptomyces / Q000737:chemistry* / Q000378:metabolism; D014127:Toyocamycin / Q000096:biosynthesis / Q000737:chemistry*
chemical_list: C512929:7-deazapurine; D002247:Carbon Isotopes; D009587:Nitrogen Isotopes; D011687:Purines; D000225:Adenine; D014127:Toyocamycin