Substrate-dependent stereospecificity of Tyl-KR1: An isolated polyketide synthase ketoreductase domain from Streptomyces fradiae

Chemistry - A European Journal

Volumn 19, Issue 27, 2013, Pages 8922-8928

  Häckh, Matthias ^a   Müller, Michael ^a   Lüdeke, Steffen ^a  

^a UNIVERSITY OF FREIBURG   (Germany)

Author keywords

enzyme catalysis; polyketides; stereoselectivity; stereospecificity; vibrational circular dichroism

Indexed keywords

ABSOLUTE CONFIGURATION; ENZYME CATALYSIS; POLYKETIDES; QUANTUM CHEMICAL CALCULATIONS; STEREOSPECIFICITY; SUBSTRATE DEPENDENCES; VIBRATIONAL CIRCULAR DICHROISM; VIBRATIONAL CIRCULAR DICHROISM SPECTROSCOPY;

BACTERIA; BINDING ENERGY; DICHROISM; ESTERIFICATION; ESTERS; KETONES; QUANTUM CHEMISTRY; STEREOCHEMISTRY; STEREOSELECTIVITY;

SUBSTRATES;

2 METHYL 3 OXOVALERIC ACID; 2-METHYL-3-OXOVALERIC ACID; ALCOHOL DEHYDROGENASE; BACTERIAL PROTEIN; POLYKETIDE; POLYKETIDE SYNTHASE; POLYKETIDE SYNTHASE KETOREDUCTASE; VALERIC ACID DERIVATIVE;

ARTICLE; CHEMISTRY; ENZYME ACTIVE SITE; ENZYMOLOGY; PROTEIN TERTIARY STRUCTURE; STEREOISOMERISM; STREPTOMYCES;

ALCOHOL OXIDOREDUCTASES; BACTERIAL PROTEINS; CATALYTIC DOMAIN; PENTANOIC ACIDS; POLYKETIDE SYNTHASES; POLYKETIDES; PROTEIN STRUCTURE, TERTIARY; STEREOISOMERISM; STREPTOMYCES;

EID: 84879420276     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201300554     Document Type: Article

References (41)

1. S. D. Copley, Curr. Opin. Chem. Biol. 2003, 7, 265-272.
2. A. Hummel, E. Brüsehaber, D. Böttcher, H. Trauthwein, K. Doderer, U. T. Bornscheuer, Angew. Chem. 2007, 119, 8644-8646
3. Angew. Chem. Int. Ed. 2007, 46, 8492-8494.
4. S. Donadio, M. J. Staver, J. B. McAlpine, S. J. Swanson, L. Katz, Science 1991, 252, 675-679.
5. D. J. Bevitt, J. Cortes, S. F. Haydock, P. F. Leadlay, Eur. J. Biochem. 1992, 204, 39-49.
6. M. Müller, Angew. Chem. 2005, 117, 366-369
7. Angew. Chem. Int. Ed. 2005, 44, 362-365.
8. S. D. Rychnovsky, Chem. Rev. 1995, 95, 2021-2040.
9. R. Castonguay, W. G. He, A. Y. Chen, C. Khosla, D. E. Cane, J. Am. Chem. Soc. 2007, 129, 13758-13769.
10. R. Castonguay, C. R. Valenzano, A. Y. Chen, A. Keatinge-Clay, C. Khosla, D. E. Cane, J. Am. Chem. Soc. 2008, 130, 11598-11599.
11. C. R. Valenzano, R. J. Lawson, A. Y. Chen, C. Khosla, D. E. Cane, J. Am. Chem. Soc. 2009, 131, 18501-18511.
12. W. D. Celmer, Antimicrob. Agents Chemother. 1965, 5, 144-156.
13. A. T. Keatinge-Clay, Chem. Biol. 2007, 14, 898-908.
14. A. P. Siskos, A. Baerga-Ortiz, S. Bali, V. Stein, H. Mamdani, D. Spiteller, B. Popovic, J. B. Spencer, J. Staunton, K. J. Weissman, P. F. Leadlay, Chem. Biol. 2005, 12, 1145-1153.
15. A. Baerga-Ortiz, B. Popovic, A. P. Siskos, H. M. O'Hare, D. Spiteller, M. G. Williams, N. Campillo, J. B. Spencer, P. F. Leadlay, Chem. Biol. 2006, 13, 277-285.
16. P. Caffrey, ChemBioChem 2003, 4, 654-657.
17. V. Prelog, Pure Appl. Chem. 1964, 9, 119-130.
18. K. Ishida, T. Lincke, C. Hertweck, Angew. Chem. 2012, 124, 5566-5570
19. Angew. Chem. Int. Ed. 2012, 51, 5470-5474.
20. D. Janssen, D. Albert, R. Jansen, R. Müller, M. Kalesse, Angew. Chem. 2007, 119, 4985-4988
21. Angew. Chem. Int. Ed. 2007, 46, 4898-4901.
22. D. Pistorius, R. Müller, ChemBioChem 2012, 13, 416-426.
23. J. Barbier, R. Jansen, H. Irschik, S. Benson, K. Gerth, B. Böhlendorf, G. Höfle, H. Reichenbach, J. Wegner, C. Zeilinger, A. Kirschning, R. Müller, Angew. Chem. 2012, 124, 1282-1286
24. Angew. Chem. Int. Ed. 2012, 51, 1256-1260.
25. C. Jahns, T. Hoffmann, S. Müller, K. Gerth, P. Washausen, G. Höfle, H. Reichenbach, M. Kalesse, R. Müller, Angew. Chem. 2012, 124, 5330-5334
26. Angew. Chem. Int. Ed. 2012, 51, 5239-5243.
27. S. K. Piasecki, C. A. Taylor, J. F. Detelich, J. Liu, J. Zheng, A. Komsoukaniants, D. R. Siegel, A. T. Keatinge-Clay, Chem. Biol. 2011, 18, 1331-1340.
28. H. Zhou, Z. Gao, K. Qiao, J. Wang, J. C. Vederas, Y. Tang, Nat. Chem. Biol. 2012, 8, 331-333.
29. T. B. Freedman, X. L. Cao, R. K. Dukor, L. A. Nafie, Chirality 2003, 15, 743-758.
30. P. J. Stephens, F. J. Devlin, J. J. Pan, Chirality 2008, 20, 643-663.
31. C. H. Wong, D. G. Drueckhammer, H. M. Sweers, J. Am. Chem. Soc. 1985, 107, 4028-4031.
32. D. V. Patel, F. Vanmiddlesworth, J. Donaubauer, P. Gannett, C. J. Sih, J. Am. Chem. Soc. 1986, 108, 4603-4614.
33. S. E. Bode, M. Müller, M. Wolberg, Org. Lett. 2002, 4, 619-621.
34. Gaussian 09, Revision B.01, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, Montgomery Jr. J.A., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, N. J. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, Ö. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, Gaussian Inc., Wallingford, CT, USA, 2009.
35. P. Caffrey, Chem. Biol. 2005, 12, 1060-1062.
36. S. Rodriguez, P. Panizza, S. Onetto, Biocatal. Biotransform. 2007, 25, 414-417.
37. W. A. Kaluzna, T. Matsuda, A. K. Sewell, J. D. Stewart, J. Am. Chem. Soc. 2004, 126, 12827-12832.
38. D. Kalaitzakis, S. Kambourakis, D. J. Rozzell, I. Smonou, Tetrahedron: Asymmetry 2007, 18, 2418-2426.
39. D. Kalaitzakis, J. D. Rozzell, S. Kambourakis, I. Smonou, Org. Lett. 2005, 7, 4799-4801.
40. A. G. Ji, M. Wolberg, W. Hummel, C. Wandrey, M. Müller, Chem. Commun. 2001, 57-58.
41. S. Lüdeke, M. Richter, M. Müller, Adv. Synth. Catal. 2009, 351, 253-259.