Biosynthesis of (-)-(1S,2R)-allocoronamic acyl thioester by an Fe II-dependent halogenase and a cyclopropane-forming flavoprotein

Journal of the American Chemical Society

Volumn 130, Issue 43, 2008, Pages 14022-14023

  Neumann, Christopher S ^a   Walsh, Christopher T ^a  

^a HARVARD MEDICAL SCHOOL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; CYCLOPROPANE; CYCLOPROPANE DERIVATIVE; FLAVOPROTEIN; ISOINDOLE DERIVATIVE; ISOLEUCINE; THIOESTER;

ARTICLE; BIOSYNTHESIS; CHEMICAL ANALYSIS; CHLORINATION; CYCLIZATION; GENE; GENE EXPRESSION; GENE OVEREXPRESSION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; INCUBATION TIME; MASS SPECTROMETRY; PROTEIN PURIFICATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

ACTINOBACTERIA; BACTERIAL PROTEINS; CARRIER PROTEINS; CHLORIDES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYCLIZATION; CYCLOPROPANES; DEUTERIUM; FLAVOPROTEINS; HALOGENATION; INDOLES; IRON; MASS SPECTROMETRY; MOLECULAR CONFORMATION; MULTIENZYME COMPLEXES; OXIDOREDUCTASES; STEREOISOMERISM; TIME FACTORS;

EID: 54849427485     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja8064667     Document Type: Article

References (15)

1. Felnagle, E. A.; Jackson, E. E.; Chan, Y. A.; Podevels, A. M.; Berti, A. D.; McMahon, M. D.; Thomas, M. G. Mol. Pharm. 2008, 5, 191-211.
2. Döhren, H. v. In Biochemistry of Peptide Antibiotics; Döhren, H. v., Kleinkauf, H., Eds.; de Gruyter: Berlin, NY, 1990; p 411-506.
3. Fujimori, D. G.; Hrvatin, S.; Neumann, C. S.; Strieker, M.; Marahiel, M. A.; Walsh, C. T. Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 16498-16503.
4. Broberg, A.; Menkis, A.; Vasiliauskas, R. J. Nat. Prod. 2006, 69, 97-102.
5. Pohanka, A.; Menkis, A.; Levenfors, J.; Broberg, A. J. Nat. Prod. 2006, 69, 1776-1781.
6. Heemstra, J. R.; Walsh, C. T. J. Am. Chem. Soc. 2008, 130, 14024-14025.
7. Neumann, C. S.; Fujimori, D. G.; Walsh, C. T. Chem. Biol. 2008, 15, 99-109.
8. Yeh, E.; Kohli, R. M.; Bruner, S. D.; Walsh, C. T. Chembiochem 2004, 5, 1290-3.
9. Vaillancourt, F. H.; Yeh, E.; Vosburg, D. A.; O'Connor, S. E.; Walsh, C. T. Nature 2005, 436, 1191-1194.
10. Fujimori, D. G.; Barr, E. W.; Walsh, C. T.; Bollinger, J. M.; Krebs, C. Nat. Chem. Biol. 2007, 3, 113-116.
11. (a) Ghisla, S.; Thorpe, C. Eur. J. Biochem. 2004, 271, 494-508.
12. (b) Mansoorabadi, S. O.; Thibodeaux, C. J.; Liu, H. J. Org. Chem. 2007, 72, 6329-6342.
13. While not common, redox inactive flavoproteins are known. For examples, see ref 11b and: Bornemann, S. Nat. Prod. Rep. 2002, 19, 761-772.
14. Walsh, C. T.; Schonbrunn, A.; Abeles, R. H. J. Biol. Chem. 1971, 246, 6855-6866.
15. Kelly, W. L.; Boyne, M. T.; Yeh, E.; Vosburg, D. A.; Galonic, D. P.; Kelleher, N. L.; Walsh, C. T. Biochemistry 2007, 46, 359-368.