title: Neopikromycin and novapikromycin from the pikromycin biosynthetic pathway of Streptomyces venezuelae.
abstract: Two new macrolides from the pikromycin biosynthetic pathway of Streptomyces venezuelae, neopikromycin (9) and novapikromycin (10), were identified and structurally characterized through mass spectrometry and NMR spectroscopy. The established structures showed that 9 and 10 have hydroxyl groups at C-14 (9) and at both C-12 and C-14 (10), on the basis of a comparison with narbomycin (7). The purified PikC cytochrome P450 monooxygenase catalyzes the in vitro hydroxylation of 7 and pikromycin (8) to yield 9 and 10, respectively, thus expanding the substrate- and regio-flexibility of this enzyme.
authors.affiliation: School of Chemical and Biological Engineering, Seoul National University, Gwanak-gu, Seoul 151-742, Korea.
authors.forename: Sang Kil
authors.initials: SK
authors.lastname: Lee
authors.forename: Je Won
authors.initials: JW
authors.lastname: Park
authors.forename: Ji Won
authors.initials: JW
authors.lastname: Kim
authors.forename: Won Seok
authors.initials: WS
authors.lastname: Jung
authors.forename: Sung Ryeol
authors.initials: SR
authors.lastname: Park
authors.forename: Cha Yong
authors.initials: CY
authors.lastname: Choi
authors.forename: Eung Soo
authors.initials: ES
authors.lastname: Kim
authors.forename: Beom Seok
authors.initials: BS
authors.lastname: Kim
authors.forename: Jong Seog
authors.initials: JS
authors.lastname: Ahn
authors.forename: David H
authors.initials: DH
authors.lastname: Sherman
authors.forename: Yeo Joon
authors.initials: YJ
authors.lastname: Yoon
mesh_terms: D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D001412:Bacillus subtilis / Q000187:drug effects; D003577:Cytochrome P-450 Enzyme System / Q000378:metabolism*; D018942:Macrolides / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D006899:Mixed Function Oxygenases / Q000378:metabolism*; D015394:Molecular Structure; D013302:Streptomyces / Q000737:chemistry* / Q000201:enzymology*; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D018942:Macrolides; C511676:neopikromycin; C511677:novapikromycin; D003577:Cytochrome P-450 Enzyme System; D006899:Mixed Function Oxygenases; C442772:PikC cytochrome P450 hydroxylase; C003145:picromycin