Neopikromycin and novapikromycin from the pikromycin biosynthetic pathway of Streptomyces venezuelae.
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.
Lee
Sang Kil
SK
School of Chemical and Biological Engineering, Seoul National University, Gwanak-gu, Seoul 151-742, Korea.
Park
Je Won
JW
Kim
Ji Won
JW
Jung
Won Seok
WS
Park
Sung Ryeol
SR
Choi
Cha Yong
CY
Kim
Eung Soo
ES
Kim
Beom Seok
BS
Ahn
Jong Seog
JS
Sherman
David H
DH
Yoon
Yeo Joon
YJ
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
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