Macrolide biosynthesis: A single cytochrome P450, PicK, is responsible for the hydroxylations that generate methymycin, neomethymycin, and picromycin in Streptomyces venezuelae

Bioorganic and Medicinal Chemistry Letters

Volumn 8, Issue 22, 1998, Pages 3117-3120

  Graziani, Edmund I ^a   Cane, David E ^a   Betlach, Melanie C ^b   Kealey, James T ^b   McDaniel, Robert ^b  

^a BROWN UNIVERSITY   (United States)

^b KOSAN BIOSCIENCES INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOCHROME P450; MACROLIDE; METHYMYCIN; NARBOMYCIN; NEOMETHYMYCIN; PIKROMYCIN; UNCLASSIFIED DRUG; UNSPECIFIC MONOOXYGENASE;

ARTICLE; DRUG HYDROXYLATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME KINETICS; REACTION ANALYSIS; STREPTOMYCES; STREPTOMYCES VENEZUELAE;

FELIS CATUS; STREPTOMYCES; STREPTOMYCES VENEZUELAE; TRIXIS;

EID: 0032541989     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(98)00553-8     Document Type: Article

References (17)

1. 1. Maezawa, I.; Kinumaki, A.; Suzuki, M. J. Antibiot. 1974, 27, 84. Donin, M. N.; Pagano, J.; Dutcher, J. D.; McKee, C. M. Antibiot. Ann. 1953-4, 1, 179. Pearlman, D.; O'Brien, E. Antibiot. Chemother. 1954, 4, 894. Rickards, R. W.; Smith, R. M.; Majer, J. J. Chem. Soc., Chem. Commun. 1968, 1049. Prelog, V.; Gold, A. M.; Talbot, G.; Zamojski, A. Helv. Chim. Acta 1962, 45, 4.
2. 1. Maezawa, I.; Kinumaki, A.; Suzuki, M. J. Antibiot. 1974, 27, 84. Donin, M. N.; Pagano, J.; Dutcher, J. D.; McKee, C. M. Antibiot. Ann. 1953-4, 1, 179. Pearlman, D.; O'Brien, E. Antibiot. Chemother. 1954, 4, 894. Rickards, R. W.; Smith, R. M.; Majer, J. J. Chem. Soc., Chem. Commun. 1968, 1049. Prelog, V.; Gold, A. M.; Talbot, G.; Zamojski, A. Helv. Chim. Acta 1962, 45, 4.
3. 1. Maezawa, I.; Kinumaki, A.; Suzuki, M. J. Antibiot. 1974, 27, 84. Donin, M. N.; Pagano, J.; Dutcher, J. D.; McKee, C. M. Antibiot. Ann. 1953-4, 1, 179. Pearlman, D.; O'Brien, E. Antibiot. Chemother. 1954, 4, 894. Rickards, R. W.; Smith, R. M.; Majer, J. J. Chem. Soc., Chem. Commun. 1968, 1049. Prelog, V.; Gold, A. M.; Talbot, G.; Zamojski, A. Helv. Chim. Acta 1962, 45, 4.
4. 1. Maezawa, I.; Kinumaki, A.; Suzuki, M. J. Antibiot. 1974, 27, 84. Donin, M. N.; Pagano, J.; Dutcher, J. D.; McKee, C. M. Antibiot. Ann. 1953-4, 1, 179. Pearlman, D.; O'Brien, E. Antibiot. Chemother. 1954, 4, 894. Rickards, R. W.; Smith, R. M.; Majer, J. J. Chem. Soc., Chem. Commun. 1968, 1049. Prelog, V.; Gold, A. M.; Talbot, G.; Zamojski, A. Helv. Chim. Acta 1962, 45, 4.
5. 1. Maezawa, I.; Kinumaki, A.; Suzuki, M. J. Antibiot. 1974, 27, 84. Donin, M. N.; Pagano, J.; Dutcher, J. D.; McKee, C. M. Antibiot. Ann. 1953-4, 1, 179. Pearlman, D.; O'Brien, E. Antibiot. Chemother. 1954, 4, 894. Rickards, R. W.; Smith, R. M.; Majer, J. J. Chem. Soc., Chem. Commun. 1968, 1049. Prelog, V.; Gold, A. M.; Talbot, G.; Zamojski, A. Helv. Chim. Acta 1962, 45, 4.
6. 2. Cane, D. E.; Lambalot, R. H.; Prabhakaran, P. C.; Ott, W. R. J. Am. Chem. Soc. 1993, 115, 522. Birch, A. J.; Pride, E.; Rickards, R. W.; Thompson, P. J.; Dutcher, J. D.; Perlman, D.; Djerassi, C. Chem. and Ind., Oct. 1 1960, 1245. Omura, S.; Takeshima, H.; Nakagawa, A.; Miyazawa, J. J. Antibiot. 1976, 29, 316.
7. 2. Cane, D. E.; Lambalot, R. H.; Prabhakaran, P. C.; Ott, W. R. J. Am. Chem. Soc. 1993, 115, 522. Birch, A. J.; Pride, E.; Rickards, R. W.; Thompson, P. J.; Dutcher, J. D.; Perlman, D.; Djerassi, C. Chem. and Ind., Oct. 1 1960, 1245. Omura, S.; Takeshima, H.; Nakagawa, A.; Miyazawa, J. J. Antibiot. 1976, 29, 316.
8. 2. Cane, D. E.; Lambalot, R. H.; Prabhakaran, P. C.; Ott, W. R. J. Am. Chem. Soc. 1993, 115, 522. Birch, A. J.; Pride, E.; Rickards, R. W.; Thompson, P. J.; Dutcher, J. D.; Perlman, D.; Djerassi, C. Chem. and Ind., Oct. 1 1960, 1245. Omura, S.; Takeshima, H.; Nakagawa, A.; Miyazawa, J. J. Antibiot. 1976, 29, 316.
9. 3. Betlach, M.; Kealey, J. T.; Betlach, M.; Ashley, G.; McDaniel, R. Biochemistry 1998, in press.
10. 4. Xue, Y.; Wilson, D.; Zhao, L.; Liu, H.-W.; Sherman, D. H. Proc. Natl. Acad. Sci. U.S.A. 1998, in press.
11. 5. Cane, D. E.; Graziani, E. I. J. Am. Chem. Soc. 1998, 120, 2682.
12. 6. Hori, T.; Maezawa, I.; Nagahama, N.; Suzuki, M. Chem. Commun. 1971, 304.
13. 7. Lambalot, R. H.; Cane, D. E. J. Antibiot. 1992, 45, 1981.
14. 8. Lambalot, R. H.; Cane, D. E.; Aparicio, J. J.; Katz, L. Biochemistry 1995, 34, 1858.
15. 4 (pH 7.3), 1 mM EDTA).
16. 10. Sherman et al. have recently shown that a picK (pikC using their nomenclature) deletion mutant of S. venezuelae accumulates both 4 and 5. See Xue, Y.; Wilson, D.; Zhao, L.; Liu, N.-W.; Sherman, D. H. Chem. & Biol. 1998, in press, and ref 4.
17. 10. Sherman et al. have recently shown that a picK (pikC using their nomenclature) deletion mutant of S. venezuelae accumulates both 4 and 5. See Xue, Y.; Wilson, D.; Zhao, L.; Liu, N.-W.; Sherman, D. H. Chem. & Biol. 1998, in press, and ref 4.