Biocatalysis of azidolysis of epoxides: Computational evidences on the role of halohydrin dehalogenase (HheC)

Journal of Chemical Sciences

Volumn 123, Issue 3, 2011, Pages 279-290

  Senthilnathan, Dhurairajan ^a   Tamilmani, Venkatachalam ^b   Venuvanalingam, Ponnambalam ^a  

^a BHARATHIDASAN UNIVERSITY   (India)

^b ANNA UNIVERSITY   (India)

Author keywords

Azidolysis of epoxide; Biocatalysis; Density functional theory; Halohydrin dehalogenase

Indexed keywords

BIOCATALYSTS; CATALYSIS; CHEMICAL ACTIVATION; COMPUTATION THEORY; CONTINUUM MECHANICS; CRYSTAL STRUCTURE; ENZYMES; GASES; HYDROGEN BONDS; NEGATIVE IONS; REGIOSELECTIVITY; SOLUTIONS; SOLVATION; STYRENE;

ACTIVE-SITE MODELING; AZIDOLYSIS; BIOCATALYSIS; CRYSTAL STRUCTURE DATA; DOMINANT CONTRIBUTIONS; HALOHYDRIN DEHALOGENASE; POLARIZABLE CONTINUUM MODEL; SECOND ORDER PERTURBATION;

DENSITY FUNCTIONAL THEORY;

EID: 79959370657     PISSN: 09743626     EISSN: 09737103     Source Type: Journal    
DOI: 10.1007/s12039-011-0082-7     Document Type: Article

References (32)

1. Archer I V J 1997 Tetrahedron 53 15617
2. Nakamura T, Nagasawa T, Yu F, Watanabe I and Yamada H 1994 Appl. Environ. Microbiol. 60 1297
3. Castro C E and Bartnicki E W 1968 Biochemistry 7 3213
4. Assis H M S, Sallis P J, Bull A T and Hardman D J 1998 Enzyme Microb. Technol. 22 568
5. Van den Wijngaard A J, Reuvekamp P TWand Janssen D B 1991 J. Bacteriol. 173 124
6. Orru R A V and Faber K 1999 Curr. Opin. Chem. Biol. 3 16
7. Patai S (Ed.) 1971 The Chemistry of Azido group. (New York: Wiley)
8. Jeffrey L S H, Johan E T, Van Hylckama V, Lixia T, Janssan D B and Kellogg R M 2001 Org. Lett. 3 41
9. Chini M, Crotti P and Macchia F 1990 Tetrahedron Lett. 31 5641
10. Blumenstein J J, Ukachukwu V C, Mohan R S and Whalen D L 1993 J. Org. Chem. 58 924
11. Hopmann H K and Fahmi H 2008 Biochemistry 47 4973
12. Kleiner C M and Schreniner P R 2006 Chem. Commun. 28 4315
13. Thomsen R and Christensen M H 2006 J. Med. Chem. 49 3315
14. Hopmann H K and Fahmi H 2008 J. Chem. Theory. Comput. 4 1129
15. Janssen D B, Majerić-Elenkov M, Hasnaoui G, Hauer B and Lutje Spelberg J H 2006 Biochem. Soc. Trans. 34 291
16. Lutje Spelberg J H, Tang L, Van Gelder M, Kellogg RM and Janssen D 2002 Tetrahedron Asymmetry. 13 1083
17. Elenkov M M, Tang L, Hauer B and Janssen D B 2006 Org. Lett. 8 4227
18. Elenkov M M, Bernhard H and Janssen D B 2006 Adv. Synth. Catal. 348 579
19. Haak RM, Tarabiono C, Janssen D B, Minnaard A J, De Varies J G and Feringa B L 2007 Org. Biomol. Chem. 5 318
20. Mladenovic M, Konstantin J, Reinhold J J, Thiel W, Schirmeister T and Engels B 2008 J. Phys. Chem. B. 112 5458
21. Frisch M J et al. 2003 Gaussian, Inc, Wallingford CT, Gaussian 03, Revision C.02
22. De Jong RM, Tiesinga J J, Rozeboom H J, Kalk H, Tang L, Janssen D B and Dijkstra P W 2003 EMBO J. 22 4933
23. Zhang X, DeChancie J, Gunaydin H, Chowdry A B, Clemente F R, Smith A J, Handel T M and Houk K N 2008 J. Org. Chem. 73 889,
24. Claeyssens F, Harvey J N, Mulholland A J, Ranaghan K E, Schütz M, Thiel S, Thiel W and Werner H J 2006 J. Angew. Chem Int. Ed. 45 6856
25. Laitinen T, Rouvinen J and Peräkylä M J 1998 J. Org. Chem. 63 8157
26. Tamami B, Iranpoor N and Mahdavi H 2002 Synth. Commun. 32 1251
27. ElenkovMM, Tang L, Meetsma A, Hauer B and Janssen D B 2008 Org. Lett. 10 2417
28. De Jone R. M, Jan J, Tiesinga W, Alessandra V, Tang L and Janssen D B 2005 J. Am. Chem. Soc. 127 13338
29. Hasnaoui G, Jeffrey H, Spelberg L, Erik de Vries, Tang L, Hauer B and Janssen D B 2005 Tetrahedron Asymmetry. 16 1685
30. XuW, Xu J H, Pan J, Qing G and Xin-YanW2006 Org. Lett. 8 1737
31. Ammantini D, Francesco F, Piermatti. O, Tortoioli S and Vaccaro L 2002 ARKIVOC. XI 293 and references Cited there in.
32. Oshima T, Haruyasu A, Kubo E, Miyamoto S and Togaya K 2008 Org. Lett. 10 2413