Synthesis of screening substrates for the directed evolution of sialic acid aldolase: Towards tailored enzymes for the preparation of influenza a sialidase inhibitor analogues

Organic and Biomolecular Chemistry

Volumn 3, Issue 9, 2005, Pages 1795-1800

  Woodhall, Thomas ^a   Williams, Gavin ^a   Berry, Alan ^a   Nelson, Adam ^a  

^a UNIVERSITY OF LEEDS   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; CHELATION; DERIVATIVES; ENZYMES; ESTERS; STEREOCHEMISTRY; SUBSTRATES; SYNTHESIS (CHEMICAL);

ALDOLS; MULTI-STEP REACTIONS; SIDE CHAINS; STEREOSELECTIVITY;

AROMATIC COMPOUNDS;

ENZYME INHIBITOR; LYASE; N ACETYLNEURAMINATE LYASE; N-ACETYLNEURAMINATE LYASE; SIALIDASE;

ARTICLE; CHEMICAL STRUCTURE; DIRECTED MOLECULAR EVOLUTION; DRUG ANTAGONISM; ENZYME SPECIFICITY; ENZYMOLOGY; GENETICS; INFLUENZA VIRUS A; METABOLISM;

DIRECTED MOLECULAR EVOLUTION; ENZYME INHIBITORS; INFLUENZA A VIRUS; MODELS, MOLECULAR; NEURAMINIDASE; OXO-ACID-LYASES; SUBSTRATE SPECIFICITY;

STAPHYLOCOCCUS PHAGE 3A;

EID: 18844391810     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b501503k     Document Type: Article

References (32)

1. C.-H. Wong and G. M. Whitesides, Enzymes in Synthetic Organic Chemistry, Tetrahedron Organic Chemistry Series, Pergamon, Oxford, 1994, vol. 12.
2. M. T. Reetz, Angew. Chem., Int. Ed., 2001, 40, 284.
3. M. Alexeeva, R. Carr and N. J. Turner, Org. Biomol, Chem., 2003, 1, 4133.
4. N. J. Turner, Trends Biotechnol., 2003, 21, 474.
5. S. Fong, T. D. Machajewski, C. C. Mak and C.-H. Wong, Chem. Biol., 2000, 7, 873.
6. G. DeSantis, K. Wong, B. Farwell, K. Chatman, Z. Zhu, G. Tomlinson, H. Huang, X. Tan, L. Bibbs, P. Chen, K. Kretz and M. J. Burk, J. Am. Chem. Soc., 2003, 125, 11476.
7. D. Zha, S. Wilensek, M. Hermes, K.-E. Jaeger and M. T. Reetz, Chem. Commun., 2001, 2664.
8. G. Gonzalez-Blasco, J. Sanz-Aparicio, B. Gonzalez, J. A. Hermoso and J. Polaina, J. Biol Chem., 2000, 275, 13708.
9. F. Buchholz, P.-P. Angrand and A. F. Stewart, Nat. Biotechnol., 1998, 16, 657.
10. J. C. Moore and F. H. Arnold, Nat. Biotechnol., 1996, 14, 458.
11. K. Chen and F. H. Arnold, Proc. Natl. Acad. Sci. USA, 1993, 90, 5618.
12. J. Hao and A. Berry, Protein Eng. Des. Sci., 2004, 17, 689.
13. K. Liebeton, A. Zonta, K. Schimossek, M. Nardini, D. Lang, B. W. Dijkstra, M. T. Reetz and K.-E. Jaeger, Chem. Biol., 2000, 7, 709.
14. O. May, P. T. Nguyen and F. H. Arnold, Nat. Biotechnol., 2000, 18, 317.
15. R. Carr, M. Alexeeva, A. Enright, T. S. C. Eve, M. J. Dawson and N. J. Turner, Angew. Chem., Int. Ed., 2003, 42, 4807.
16. G. J. Williams, S. Domann, A. Nelson and A. Berry, Proc. Natl. Acad. Sei. USA, 2003, 100, 3143.
17. M. Wada, C.-C. Hsu, D. Franke, M. Mitchell, A. Heine, I. Wilson and C.-H. Wong, Bioorg. Med. Chem., 2003, 11, 2091.
18. M. von Itzstein, W. Y. Wu, G. B. Kok, M. S. Pegg, J. C. Dyason, B. Jin, T. Van Phan, M. L. Smythe, H. F. White and S. W. Oliver, Nature, 1993, 363, 418.
19. F. G. Hayden, J. J. Treanor, R. F. Betts, M. Lobo, J. D. Esinhart and E. K. Hussey, J. Amer. Med. Assoc., 1996, 275, 295.
20. P. W. Smith, S. L. Sollis, P. D. Howes, P. C. Cherry, I. D. Starkey, K. N. Cobley, H. Weston, J. Scicinski, A. Merritt, A. Whittington, P. Wyatt, N. Taylor, D. Green, R. Bethell, S. Madar, R. J. Fenton, P. J. Morley, T. Pateman and A. Beresford, J. Med. Chem., 1998, 41, 787.
21. N. R. Taylor, A. Cleasby, O. Singh, T. Skarzynski, A. J. Wonacott, P. W. Smith, S. L. Sollis, P. D. Howes, P. C. Cherry, R. Bethell, P. Colman and J. Varghese, J. Med. Chem., 1998, 41, 798.
22. W. Fitz, J.-R. Schwark and C.-H. Wong, J. Org. Chem., 1995, 60, 3663.
23. S. G. Davies, S. W. Epstein, A. C. Garner, O. Ichihara and A. D. Smith, Tetrahedron: Asymmetry, 2002, 13, 1555.
24. D. J. Dixon, A. C. Foster, S. V. Ley and D. J. Reynolds, J. Chem. Soc., Perkin Trans. 1, 1999, 1631.
25. N. Cohen, B. L. Banner, A. J. Laurenzano and L. Carozza, Org. Synth., 1985, 63, 127.
26. T. H. Chan and C. J. Li, J. Chem. Soc., Chem. Commun., 1992, 747.
27. M. D. Chappell and R. L. Halcomb, Org. Lett., 2000, 2, 2003.
28. C.-J. Li and T.-H. Chan, Tetrahedron, 1999, 55, 11149.
29. M. Cherest, H. Felkin and N. Prudent, Tetrahedron Lett., 1968, 2199.
30. M. T. Reetz, Angew. Chem., 1984, 96, 542.
31. D. H. R. Barton, J. Camara, X. Cheng, S. D. Gero, J. Cs. Jaszberenyi and B. Quiclet-Sire, Tetrahedron, 1992, 48, 9261.
32. T. Woodhall, G. J. Williams, A. Nelson and A. Berry, Angew. Chem., Int. Ed., 2005, 44, 2109.