Engineered biosynthesis of novel polyketides from Streptomyces spore pigment polyketide synthases

Journal of the American Chemical Society

Volumn 120, Issue 31, 1998, Pages 7749-7759

  Yu, Tin Wein ^a,b   Shen, Yuemao ^a,e   McDaniel, Robert ^c   Floss, Heinz G ^a   Khosla, Chaitan ^c,d   Hopwood, David A ^b   Moore, Bradley S ^a  

^a UNIVERSITY OF WASHINGTON   (United States)

^b JOHN INNES CENTRE   (United Kingdom)

^c Stanford University   (United States)

^d STANFORD UNIVERSITY   (United States)

^e INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

Author keywords

[No Author keywords available]

Indexed keywords

POLYCYCLIC AROMATIC COMPOUND; POLYKETIDE; SYNTHETASE;

ARTICLE; BACTERIAL SPORE; BIOSYNTHESIS; CYCLIZATION; ENZYME SUBUNIT; GENE CLUSTER; GENETIC ENGINEERING; NONHUMAN; OPEN READING FRAME; STEREOCHEMISTRY; STREPTOMYCES; SYNTHESIS;

EID: 0032511416     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9803658     Document Type: Article

References (29)

1. Davis, N. K.; Chater, K. F. Mol. Microbiol. 1990, 4, 1679-1691.
2. Fernández Moreno, M. A.; Martínez, E.; Boto, L.; Hopwood, D. A.; Malpartida, F. J. Biol. Chem. 1992, 267, 19278-19290.
3. O'Hagan, D. The Polyketide Metabolites; Ellis Horwood: Chichester, 1991.
4. Hopwood, D. A. Chem. Rev. 1997, 97, 2465-2497.
5. Blanco, G.; Pereda, A.; Méndez, C.; Salas, J. A. Gene 1992, 112, 67-76.
6. Bergh, S.; Uhlén, M. Gene 1992, 117, 131-136.
7. Deuterium substitution typically causes upfield shifts of the carbon atoms α (0.3-0.6 ppm) and β (0.1-0.3 ppm) to the deuterium atom. Hansen, P. E. Annu. Rep. NMR Spectrosc. 1983, 15, 105-234.
8. For ordinary phenols, β-isotope shifts are between 0.12 and 0.15 ppm and γ-isotope shifts are between 0.05 and 0.11 ppm. Newmark, R. A.; Hill, J. R. Org. Magn. Reson. 1980, 13, 39-44.
9. Zhang, H.-I.; He, X.-g.; Adefarati, A.; Gallucci, J.; Cole, S. P.; Beale, J. M.; Keller, P. J.; Chang, C.-j.; Floss, H. G. J. Org. Chem. 1990, 55, 1682-1684.
10. Meurer, G.; Gerlitz, M.; Wendt-Pienkowski, E.; Vining, L. C.; Rohr, J.; Hutchinson, C. R. Chem. Biol. 1997, 4, 433-443.
11. McDaniel, R.; Hutchinson, C. R.; Khosla, C. J. Am. Chem. Soc. 1995, 117, 6805-6810.
12. McDaniel, R.; Ebert-Khosla, S.; Hopwood, D. A.; Khosla, C. J. Am. Chem. Soc. 1993, 115, 11671-11675.
13. 13C NMR-Spektroskopie; Georg Thieme Verlag: Stuttgart, 1984.
14. Summers, R. G.; Wendt-Pienkowski, E.; Motamedi, H.; Hutchinson, C. R. J. Bacteriol. 1992, 174, 1810-1820.
15. Summers, R. G.; Wendt-Pienkowski, E.; Motamedi, H.; Hutchinson, C. R. J. Bacteriol. 1993, 175, 7571-7580.
16. Shen, B.; Summers, R. G.; Wendt-Pienkowski, E.; Hutchinson, C. R. J. Am. Chem. Soc. 1995, 117, 6811-6821.
17. 18 (Figure 3), which is racemic at C9, is thought to be formed in such a manner.
18. Fu, H.; McDaniel, R.; Hopwood, D. A.; Khosla, C. Biochemistry 1994, 33, 9321-9326.
19. Alvarez, M. A.; Fu, H.; Khosla, C.; Hopwood, D. A.; Bailey, J. E. Nat. Biotechnol. 1996, 14, 335-338.
20. A similar post-PKS reduction by a S. coelicolor-encoded dehydrogenase has recently been proposed to account for the observed ketoreduction of an eight-membered ring lactone generated from an engineered derivative of the 6-deoxyerythronilide B synthase. Kao, C. M.; McPherson, M.; McDaniel, R. N.; Fu, H.; Cane, D. E.; Khosla, C. J. Am. Chem. Soc. 1997, 119, 11339-11340.
21. Perkins, E. J.; Gordon, M. P.; Caceres, O.; Lurquin, P. F. J. Bacteriol. 1990, 72, 2351-2359.
22. Brown, D. W.; Hauser, F. M.; Tommasi, R.; Corlett, S.; Salvo, J. J. Tetrahedron Lett. 1993, 34, 419-422.
23. Brown, D. W.; Salvo, J. J. Appl. Environ. Microbiol. 1994, 60, 979-983.
24. Mayorga, M. E.; Timberlake, W. E. Mol. Gen. Genet. 1992, 235, 205-212.
25. Bax, A.; Subramanian, S. J. Magn. Reson. 1986, 67, 565-569.
26. Bax, A.; Summers, M. F. J. Am. Chem. Soc. 1986, 108, 2093-2094.
27. Reynolds, W. F.; McLean, S.; Perpick-Dumont, M.; Enriquez, R. G. Magn. Reson. Chem. 1989, 27, 162-169.
28. Hopwood, D. A.; Bibb, M. J.; Chater, K. F.; Kieser, T.; Bruton, C. J.; Kieser, H. M.; Lydiate, D. J.; Smith, C. P.; Ward, J. M.; Schrempf, H. Genetic Manipulations of Streptomyces: A Laboratory Manual; The John Innes Foundation: Norwich, 1985.
29. Sambrook, J.; Fritsch, E. F.; Maniatis, T. Molecular Cloning, a Laboratory Manual; Cold Spring Harbor Laboratory Press: Cold Spring Harbor, NY, 1989.