Creation of a pair of stereochemically complementary biocatalysts

Journal of the American Chemical Society

Volumn 128, Issue 50, 2006, Pages 16238-16247

  Williams, Gavin J ^a   Woodhall, Thomas ^a   Farnsworth, Lorna M ^a   Nelson, Adam ^a   Berry, Alan ^a  

^a UNIVERSITY OF LEEDS   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON CARBON COMPOSITES; CATALYSIS; CONDENSATION; MUTAGENESIS; REACTION KINETICS; STEREOCHEMISTRY;

ALDOLASES; BIOLOGICALLY ACTIVE MOLECULES; SIALIC ACID; SITE-DIRECTED MUTAGENESIS;

BIOCATALYSTS;

2,3 DIHYDROXY 4 OXO N,N DIPROPYLBUTYRAMIDE; AMIDE; CARBON; FRUCTOSE BISPHOSPHATE ALDOLASE; HYDROXYL GROUP; LYASE; N ACETYLNEURAMINIC ACID DERIVATIVE; PROPANE; PYRUVIC ACID; SIALIC ACID;

ARTICLE; BIOCATALYST; CATALYSIS; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; DIASTEREOISOMER; POLYMERASE CHAIN REACTION; POLYMERIZATION; REACTION ANALYSIS; SITE DIRECTED MUTAGENESIS; STEREOCHEMISTRY; SYNTHESIS; THERMODYNAMICS; WILD TYPE;

ALDEHYDES; BIOMIMETIC MATERIALS; CATALYSIS; EVOLUTION, MOLECULAR; KINETICS; LYASES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; MUTATION; N-ACETYLNEURAMINIC ACID; STEREOISOMERISM; VARIATION (GENETICS);

EID: 33845572441     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja065233q     Document Type: Article

References (49)

1. Liese, A.; Seelbach, K.; Wandrey, C. Industrial Biotransformations; Wiley-VCH: Weinheim, Germany, 2000.
2. Schmidt-Dannert, C.; Arnold, F. H. Trends Biotechnol. 1999, 17, 135-136.
3. Silvestri, M.; DeSantis, G.; Mitchell, M.; Wong, C. H. Top. Stereochem. 2003, 23, 267-342.
4. Straathof, A. J. J.; Panke, S.; Schmid, A. Curr. Opin. Biotechnol. 2002, 13, 548-556.
5. Thayer, A. M. Chem. Eng. News. Aug 14, 2006, pp 15-25.
6. Rouhi, A. M. Chem. Eng. News, Jun 14, 2004, pp 47-62.
7. DeSantis, G.; Zhu, Z.; Greenberg, W. A.; Wong, K.; Chaplin, J.; Hanson, S. R.; Harwell, B.; Nicholson, L. W. R.; Weiner, C. L. J. Am. Chem. Soc. 2002, 124, 9024-9025.
8. Greenberg, W. A.; Varvak, A.; Hanson, S. R.; Wong, K.; Huang, H.; Chen, P.; Burk, M. J. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5788-5793.
9. Reetz, M. Adv. Catal. 2006, 49, 1-69.
10. Liebeton, K.; Zonta, A.; Schimossek, K.; Nardini, M.; Lang, D.; Dijkstra, B. W.; Reetz, M. T.; Jaeger, K. E. Chem. Biol. 2000, 7, 709-718.
11. May, O.; Nguyen, P. T.; Arnold, F. H. Nat. Biotechnol. 2000, 18, 317-320.
12. Reetz, M. T.; Torre, C.; Eipper, A.; Lohmer, R.; Hermes, M.; Brunner, B.; Maichele, A.; Bocola, M.; Arand, M.; Cronin, A.; Genzel, Y.; Archelas, A.; Furstoss, R. Org. Lett. 2004, 6, 177-180.
13. Horsman, G. P.; Liu, A. M. F.; Henke, E.; Bornscheuer, U. T.; Kazlauskas, R. J. Chem. Eur. J. 2003, 9, 1933-1939.
14. Fong, S.; Machajewski, T. D.; Mak, C. C.; Wong, C. Chem. Biol. 2000, 7, 873-883.
15. Alexeeva, M.; Enright, A.; Dawson, M. J.; Mahmoudian, M.; Turner, N. J. Angew. Chem., Int. Ed. 2002, 41, 3177.
16. Jiang, R. T.; Dahnke, T.; Tsai, M. D. J. Am. Chem. Soc. 1991, 113, 5485-5486.
17. Nakajima, K.; Kato, H.; Oda, J.; Yamada, Y.; Hashimoto, T. J Biol. Chem. 1999, 274, 16563-16568.
18. van Den Heuvel, R. H.; Fraaije, M. W.; Ferrer, M.; Mattevi, A.; van Berkel, W. J. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 9455-9460.
19. Williams, G. J.; Domann, S.; Nelson, A.; Berry, A. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 3143-3148.
20. Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Pergamon: Oxford, 1994.
21. Gijsen, H. J. M.; Qiao, L.; Fitz, W.; Wong, C. H. Chem. Rev. 1996, 96, 443-473.
22. Breuer, M.; Hauer, B. Curr. Opin. Biotechnol. 2003, 14, 570-576.
23. Machajewski, T. D.; Wong, C. H. Angew. Chem., Int. Ed. 2000, 39, 1352-1374.
24. Wagner, J.; Lerner, R. A.; Barbas, C. F. Science 1995, 270, 1797-1800.
25. Barbas, C. F.; Heine, A.; Zhong, G. F.; Hoffmann, T.; Gramatikova, S.; Bjornestedt, R.; List, B.; Anderson, J.; Stura, E. A.; Wilson, I. A.; Lerner, R. A. Science 1997, 278, 2085-2092.
26. Zhong, G.; Lerner, R. A.; Barbas, C. F. Angew. Chem., Int. Ed. 1999, 38, 3738-3741.
27. Nothrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798-6799.
28. Bogevig, A.; Kumaragurubaran, N.; Jorgensen, K. A. Chem. Commun. 2002, 620-621.
29. Trost, B. M.; Ito, H. J. Am. Chem. Soc. 2000, 122, 12003-12004.
30. Biology of Sialic acids: Plenum Press: New York and London, 1995.
31. McGuire, E. J. In The Biology of Sialic Acids; Rosenberg, A., Schengrund, C. L., Eds.; Plenum Publishing Corp.: New York, 1976.
32. Koketsu, M.; Nitoda, T.; Sugino, H.; Juneja, L. R.; Kim, M.; Yamamoto, T.; Abe, N.; Kajimoto, T.; Wong, C. H. J. Med. Chem. 1997, 40, 3332-3335.
33. Babu, Y. S.; Chand, P.; Bantia, S.; Kotian, P.; Dehghani, A.; El-Kattan, Y.; Lin, T.-H.; Hutchinson, T. L.; Elliott, A. J.; Parker, C. D.; Ananth, S. L.; Horn, L. L.; Laver, G. W.; Montgomery, J. A. J. Med. Chem. 2000, 43, 3482-3486.
34. Williams, G. J.; Woodhall, T.; Nelson, A.; Berry, A. PEDS 2005, 18, 239-246.
35. Woodhall, T.; Williams, G. J.; Berry, A.; Nelson, A. Angew. Chem., Int. Ed. 2005, 44, 2109-2112.
36. Smith, B. J.; Lawrence, M. C.; Barbosa, J. A. R. G. J. Org. Chem. 1999, 64, 945-949.
37. Theodossis, A.; Walden, H.; Westwick, E. J.; Connaris, H.; Lamble, H. J.; Hough, D. W.; Danson, M. J.; Taylor, G. L. J. Biol. Chem. 2004, 279, 43886-43892.
38. Barbosa, J. A. R. G.; Smith, B. J.; DeGori, R.; Ooi, H. C.; Marcuccio, S. M.; Campi, E. M.; Jackson, W. R.; Brossmer, R.; Sommer, M.; Lawrence, M. C. J. Mol. Biol. 2000, 303, 405-421.
39. Fitz, W.; Schwark, J. R.; Wong, C. H. J. Org. Chem. 1995, 60, 3663-3670.
40. Lin, C.-H.; Sugai, T.; Halcomb, R. L.; Ichikawa, Y.; Wong, C.-H. J. Am. Chem. Soc. 1992, 114, 10138-10145.
41. Reikofski, Y.; Tao, B. Y. Biotechnol. Adv. 1992, 10, 535-547.
42. Cleland. W. W. Methods Enzymol. 1979, 63, 103-138.
43. Woodhall, T.; Williams, G. J.; Berry, A.; Nelson, A. Org. Biomol. Chem 2005, 3, 1795-1800.
44. Fersht, A. R. Structure and Mechanism in Protein Science: A guide to catalysis and protein folding; W. H. Freeman and Co.: New York, 1999.
45. Zaccolo, M.; Gherardi, E. J. Mol. Biol. 1999, 285, 775-783.
46. Matsumura, I.; Ellington, A. D. J. Mol. Biol. 2001, 305, 331-339.
47. Izard, T.; Lawrence, M. C.; Malby, R. L.; Lilley, G. G.; Colman, P. M. Structure 1994, 2, 361-369.
48. Fersht, A. R.; Matouschek, A.; Serrano, L. J. Mol. Biol. 1992, 224, 771-782.
49. You, L.; Arnold, F. H. Protein Eng 1996, 9, 77-83.