Alteration of the substrate's prefolded conformation and cyclization stereochemistry of oxidosqualene-lanosterol cyclase of saccharomyces cerevisiae by substitution at Phenylalanine 699

Organic Letters

Volumn 12, Issue 3, 2010, Pages 500-503

  Wu, Tung Kung ^a   Chang, Cheng Hsiang ^a   Wen, Hao Yu ^a   Liu, Yuan Ting ^a   Li, Wen Hsuan ^a   Wang, Tsai Ting ^a   Shie, Wen Shiang ^a  

^a NATIONAL CHIAO TUNG UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

LANOSTEROL SYNTHASE; MUTASE; PHENYLALANINE; SACCHAROMYCES CEREVISIAE PROTEIN;

AMINO ACID SEQUENCE; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; ENZYMOLOGY; GENETICS; METABOLISM; MOLECULAR GENETICS; SACCHAROMYCES CEREVISIAE; SEQUENCE HOMOLOGY; SITE DIRECTED MUTAGENESIS;

AMINO ACID SEQUENCE; CATALYSIS; CYCLIZATION; INTRAMOLECULAR TRANSFERASES; MOLECULAR SEQUENCE DATA; MOLECULAR STRUCTURE; MUTAGENESIS, SITE-DIRECTED; PHENYLALANINE; SACCHAROMYCES CEREVISIAE; SACCHAROMYCES CEREVISIAE PROTEINS; SEQUENCE HOMOLOGY, AMINO ACID;

EID: 75749148745     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol902694y     Document Type: Article

References (51)

1. (a) Bolon, D. N.; Voigt, C. A.; Mayo, S. L. Curr. Opin. Chem. Biol. 2002, 6, 125-129.
2. (b) Yoshikuni, Y.; Ferrin, T. E.; Keasling, J. D. Nature 2006, 440, 1078-1082.
3. (c) Glasner, M. E.; Gerlt, J. A.; Babbitt, P. C. Adv. Enzymol. Relat. Areas Mol. Biol. 2007, 75, 193-239.
4. (a) Abe, I.; Rohmer, M.; Prestwich, G. D. Chem. Rev. 1993, 93, 2189-2206.
5. (b) Wendt, K. U.; Schulz, G. E.; Corey, E. J.; Liu, D. R. Angew. Chem., Int. Ed. 2000, 39, 2812-2833.
6. (c) Xu, R.; Fazio, G. C.; Matsuda, S. P. T. Phytochemistry 2004, 65, 261-291.
7. (d) Abe, I. Nat. Prod. Rep. 2007, 24, 1311-1331.
8. (a) Wu, T. K.; Chang, C. H.; Liu, Y. T.; Wang, T. T. Chem. Rec. 2008, 8, 302-325.
9. (b) Wu, T. K.; Griffin, J. H. Biochemistry 2002, 41, 8238-8244.
10. (c) Wu, T. K.; Chang, C. H. ChemBioChem 2004, 5, 1712-1715.
11. (d) Wu, T. K.; Liu, Y. T.; Chang, C. H. ChemBioChem 2005, 6, 1177-1181.
12. (e) Wu, T. K.; Yu, M. T.; Liu, Y. T.; Chang, C. H.; Wang, H. J.; Diau, E. W. G. Org. Lett. 2006, 8, 1319-1322.
13. (t) Wu, T. K.; Liu, Y. T.; Chang, C. H.; Yu, M. T.; Wang, H. J. J. Am. Chem. Soc. 2006, 128, 6414-6419.
14. (g) Wu, T. K.; Liu, Y. T.; Chiu, F. H.; Chang, C. H. Org. Lett. 2006, 8, 4691-4694.
15. (h) Wu, T. K.; Wen, H. Y.; Chang, C. H.; Liu, Y. T. Org. Lett. 2008, 10, 2529-2532.
16. (i) Wu, T. K.; Wang, T. T.; Chang, C. H.; Liu, Y. T. Org. Lett. 2008, 10, 4959-4962.
17. (j) Wu, T. K.; Li, W.-H.; Chang, C.-H.; Wen, H.-Y.; Liu, Y.-T.; Chang, Y.-C. Eur. J. Org. Chem. 2009, 5731-5737.
18. (a) Abe, I.; Sankawa, U.; Ebizuka, Y. Chem. Pharm. Bull. 1989, 37, 536-538.
19. (b) Kelly, R.; Miller, S. M.; Lai, M. H.; Kirsch, D. R. Gene 1990, 87, 177-183.
20. (c) Buntel, C. J.; Griffin, J. H. J. Am. Chem. Soc. 1992, 114, 9711-9713.
21. (d) Shi, Z.; Buntel, C. J.; Griffin, J. H. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 7370-7374.
22. (a) Corey, E. J.; Matsuda, S. P.; Bartel, B. Proc Natl. Acad. Sci. U.S.A. 1993, 90, 11628-11632.
23. (b) Corey, E. J.; Matsuda, S. P. T.; Bartel, B. Proc Natl. Acad. Sci. U.S.A. 1994, 91, 2211-2215.
24. (c) Baker, C. H.; Matsuda, S. P. T.; Liu, D. R.; Corey, E. J. Biochem. Biophys. Res. Commun. 1995, 213, 154-160.
25. (d) Herrera, J. B.; Bartel, B.; Wilson, W. K.; Matsuda, S. P. Phytochemistry 1998, 49, 1905-1911.
26. (e) Segura, M. J.; Meyer, M. M.; Matsuda, S. P. Org. Lett. 2000, 2, 2257-2259.
27. (f) Corey, E. J.; Virgil, S. C. J. Am. Chem. Soc. 1991, 113, 4025-4026.
28. (g) Corey, E. J.; Virgil, S. C.; Cheng, H.; Baker, C. H.; Matsuda, S. P. T.; Singh, V.; Sarshar, S. J. Am. Chem. Soc. 1995, 117, 11819-11820.
29. (h) Corey, E. J.; Cheng, H.; Baker, C. H.; Matsuda, S. P. T.; Li, D.; Song, X. J. Am. Chem. Soc. 1997, 119, 1289-1296.
30. (i) Hart, E. A.; Hua, L.; Darr, L. B.; Wilson, W. K.; Pang, J.; Matsuda, S. P. T. J. Am. Chem. Soc. 1999, 121, 9887-9888.
31. (j) Joubert, B. M.; Hua, L.; Matsuda, S. P. T. Org. Lett. 2000, 2, 339-341.
32. (k) Meyer, M. M.; Segura, M. J. R.; Wilson, W. K.; Matsuda, S. P. T. Angew. Chem., Int. Ed. 2000, 39, 4090-4092.
33. Lodeiro, S.; Segura, M. J.; Stahl, M.; Schulz-Gasch, T.; Matsuda, S. P. T. ChemBioChem 2004, 5, 1581-1585.
34. (m) Phillips, D. R.; Rasbery, J. M.; Bartel, B.; Matsuda, S. P. Curr. Opin. Plant Biol. 2006, 9, 305-314.
35. (n) Herrera, J. B.; Wilson, W. K.; Matsuda, S. P. T. J. Am. Chem. Soc. 2000, 122, 6765-6766.
36. (o) Xiong, Q.; Wilson, W. K.; Matsuda, S. P. Angew. Chem., Int. Ed. 2006, 45, 1285-1288.
37. (p) Lodeiro, S.; Xiong, Q.; Wilson, W. K.; Kolesnikova, M. D.; Onak, C. S.; Matsuda, S. P. J. Am. Chem. Soc. 2007, 129, 11213-11222.
38. (q) Corey, E. J.; Ortiz de Montellano, P. R.; Yamamoto, H. J. Am. Chem. Soc. 1968, 90, 6245-6255.
39. (r) Corey, E. J.; Lin, K.; Yamamoto, H. J. Am. Chem. Soc. 1969, 91, 2132-2134.
40. (s) Corey, E. J.; Virgil, S. C.; Sarshar, S. J. Am. Chem. Soc. 1991, 113, 8171-8172.
41. (t) Lodeiro, S.; Xiong, Q.; Wilson, W. K.; Ivanova, Y.; Smith, M. L.; May, G. S.; Matsuda, S. P. Org. Lett. 2009, 11, 1241-1244.
42. (a) Connolly, J. D.; Hill, R. A. Nat. Prod. Rep. 2002, 19, 494-513.
43. (b) Kushiro, T.; Shibuya, M.; Ebizuka, Y. Eur. J. Biochem. 1998, 256, 238-244.
44. (c) Husselstein-Muller, T.; Schaller, H.; Benveniste, P. Plant Mol. Biol. 2001, 45, 75-92.
45. (d) Schulz-Gasch, T.; Stahl, M. J. Comput. Chem. 2003, 24, 741-753.
46. (a) Thoma, R.; Schulz-Gasch, T.; D'Arcy, B.; Benz, J.; Aebi, J.; Dehmlow, H.; Hennig, M.; Stihle, M.; Ruf, A. Nature 2004, 432, 118-122.
47. (b) Wendt, K. U. Angew. Chem., Int. Ed. 2005, 44, 3966-3971.
48. (a) Eschenmoser, A.; Ruzicka, L.; Jeger, O.; Arigoni, D. Helv. Chim. Acta 1955, 38, 1890-1904.
49. (b) Cornforth, J. W. Angew. Chem., Int. Ed. Engl. 1968, 7, 903-911.
50. (a) Hoshino, T.; Kouda, M.; Abe, T.; Ohashi, S. Biosci. Biotechnol. Biochem. 1999, 63, 2038-2041.
51. Merkofer, T.; Pale-Grosdemange, C.; Rohmer, M.; Poralla, K. Tetrahedron Lett. 1999, 40, 2121-2124.