The zinc complex catalyzed hydration of alkyl isothiocyanates

Journal of Molecular Modeling

Volumn 15, Issue 4, 2009, Pages 433-446

  Eger, Wilhelm A ^a   Jahn, Burkhard O ^a   Anders, Ernst ^a  

^a FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

Author keywords

Carbonic anhydrase; Density functional calculations; Enzyme models; Isothiocyanate fixation

Indexed keywords

CARBON DIOXIDE; ISOTHIOCYANIC ACID; WATER; ZINC COMPLEX;

ARTICLE; CALCULATION; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENERGY; ENZYME ACTIVATION; ENZYME ACTIVE SITE; ENZYME KINETICS; ENZYME MECHANISM; GIBBS FREE ENERGY; HYDRATION; PHASE TRANSITION; PRIORITY JOURNAL; PROCESS OPTIMIZATION; SURFACE PROPERTY;

CATALYSIS; ISOTHIOCYANATES; MODELS, CHEMICAL; THERMODYNAMICS; ZINC;

EID: 60849106244     PISSN: 16102940     EISSN: 09485023     Source Type: Journal    
DOI: 10.1007/s00894-008-0385-x     Document Type: Article

References (59)

1. Thoms S (2002) J Theor Biol 215:399-404. doi: 10.1006/jtbi.2002.2528
2. Bertini I, Luchinat C (1983) Acc Chem Res 16:272-279. doi: 10.1021/ ar00092a002
3. Silverman DN, Lindskog S (1988) Acc Chem Res 21:30-36. doi: 10.1021/ ar00145a005
4. Christianson DW, Fierke CA (1996) Acc Chem Res 29:331-339. doi: 10.1021/ ar9501232
5. Lipscomb WN, Norbert S (1996) Chem Rev 96:2375-2433. doi: 10.1021/ cr950042j
6. Maren TH (1967) Physiol Rev 47:595-781
7. Tashian RE (1989) Bioessays 10:186-192. doi: 10.1002/bies.950100603
8. Khalifah RG (1971) J Biol Chem 246:2561-2573
9. Heck RW, Boriack-Sjodin AP, Qian M, Tu C, Christianson WD, Laipis JP, Silverman ND (1996) Biochemistry 35:11605-11611. doi: 10.1021/bi9608018
10. Hartmann M, Clark T, van Eldik R (1996) J Mol Model 2:358-361. doi: 10.1007/s0089460020358
11. Hartmann M, Merz JKM, van Eldik R, Clark T (1998) J Mol Model 4:355-365. doi: 10.1007/s008940050094
12. Merz JKM, Hoffmann R, Dewar MJS (1989) J Am Chem Soc 111:5636-5649. doi: 10.1021/ja00197a021
13. Muguruma C (1999) THEOCHEM 461-462:439-452. doi: 10.1016/ S0166-1280(98)00455-2
14. Schenk S, Kesselmeier J, Anders E (2004) Chem Eur J 10:3091-3105. doi: 10.1002/chem.200305754
15. Notni J, Schenk S, Protschill-Krebs G, Kesselmeier J, Anders E (2007) ChemBioChem 8:530-536. doi: 10.1002/cbic.200600436
16. Notni J, Schenk S, Görls H, Breitzke H, Anders E (2008) Inorg Chem 47:1382-1390. doi: 10.1021/ic701899u
17. Mauksch M, Bräuer M, Weston J, Anders E (2001) ChemBioChem 2:190-198. doi: 10.1002/ 1439-7633(20010302)2:3<190::AID-CBIC190>3.0.CO;2-7
18. Schröder D, Schwarz H, Schenk S, Anders E (2003) Angew Chem Int Ed 42:5087-5090. doi: 10.1002/anie.200351440
19. Prince RH, Woolley PR (1973) Bioorg Chem 2:337-344. doi: 10.1016/ 0045-2068(73)90034-5
20. Tautermann CS, Loferer MJ, Voegele AF, Liedl KR (2003) J Phys Chem B 107:12013-12020. doi: 10.1021/jp0353789
21. Sola M, Lledos A, Duran M, Bertran J (1992) J Am Chem Soc 114:869-877. doi: 10.1021/ja00029a010
22. Pocker Y, Deits TL (1982) J Am Chem Soc 104:2424-2434. doi: 10.1021/ ja00373a016
23. Nakata K, Shimomura N, Shiina N, Izumi M, Ichikawa K, Shiro M (2002) J Inorg Biochem 89:255-266. doi: 10.1016/S0162-0134(01)00419-6
24. Lee C, Yang W, Parr RG (1988) Phys Rev B Condens Matter Mater Phys 37:785-789
25. Becke AD (1993) J Chem Phys 98:5648-5652. doi: 10.1063/1.464913
26. McLean AD, Chandler GS (1980) J Chem Phys 72:5639-5648. doi: 10.1063/ 1.438980
27. Krishnan R, Binkley JS, Seeger R, Pople JA (1980) J Chem Phys 72:650-654. doi: 10.1063/1.438955
28. Frisch MJ, Head-Gordon M, Pople JA (1990) Chem Phys Lett 166:275-280. doi: 10.1016/0009-2614(90)80029-D
29. Head-Gordon M, Pople JA, Frisch MJ (1988) Chem Phys Lett 153:503-506. doi: 10.1016/0009-2614(88)85250-3
30. David EW, Dunning TH Jr (1993) J Chem Phys 98:1358-1371. doi: 10.1063/ 1.464634
31. Rick AK, Dunning TH Jr, Robert JH (1992) J Chem Phys 96:6796-6806. doi: 10.1063/1.462569
32. Barone V, Cossi M (1998) J Phys Chem A 102:1995-2001. doi: 10.1021/ jp9716997
33. Cossi M, Rega N, Scalmani G, Barone V (2003) J Comput Chem 24:669-681. doi: 10.1002/jcc.10189
34. Klamt A, Schüürmann G (1993) J Chem Soc Perkin Trans 2:799-805. doi: 10.1039/p29930000799
35. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA Jr, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA (2004) Gaussian03 revision D.01. Gaussian, Inc., Wallingford, CT
36. Glendening ED, Badenhoop JK, Reed AE, Carpenter JE, Bohmann JA, Morales CM, Weinhold F (2001) NBO 5.0 Theroretical Chemistry Institute, University of Winsconsin, Madison
37. Reed AE, Curtiss LA, Weinhold F (1988) Chem Rev 88:899-926. doi: 10.1021/ cr00088a005
38. Reed AE, Weinstock RB, Weinhold F (1985) J Chem Phys 83:735-746. doi: 10.1063/1.449486
39. Reed AE, Weinhold F (1983) J Chem Phys 78:4066-4073. doi: 10.1063/ 1.445134
40. Hagemann H (1983) Methoden d.r Organischen Chemie (Houben-Weyl): Kohlensaeure-Derivate. Georg Thieme Verlag, Stuttgart
41. Walter W, Bode KD (1967) Angew 7:285-328. doi: 10.1002/ange.19670790702
42. Browne DW, Dyson GM (1931) J Chem Soc 3285-3308. doi: 10.1039/ jr9310003285
43. Rao CNR, Venkataraghavan R (1962) Tetrahedron 18:531-537. doi: 10.1016/ S0040-4020(01)92703-6
44. Harris JF (1960) J Am Chem Soc 82:155-158. doi: 10.1021/ja01486a036
45. Hadad CM, Rablen PR, Wiberg KB (1998) J Org Chem 63:8668-8681. doi: 10.1021/jo972180+
46. Nilsson Lill SO, Rauhut G, Anders E (2003) Chem Eur J 9:3143-3153. doi: 10.1002/chem.200304878
47. Bottoni A, Lanza CZ, Miscione GP, Spinelli D (2004) J Am Chem Soc 126:1542-1550. doi: 10.1021/ja030336j
48. Kimura E (2001) Acc Chem Res 34:171-179. doi: 10.1021/ar000001w
49. Mulliken RS (1955) J Chem Phys 23:1833-1840. doi: 10.1063/1.1740588
50. Fonseca Guerra C, Handgraaf J-W, Baerends EJ, Bickelhaupt FM (2004) J Comput Chem 25:189-210. doi: 10.1002/jcc.10351
51. Eriksson AE, Jones TA, Liljas A (1988) Prot Struct Funct Genet 4:274-282. doi: 10.1002/prot.340040406
52. Lindskog S, Engberg P, Forsman C, Ibrahim AS, Jonsson HB, Simonsson I, Tibell L (1987) Ann N Y Acad Sci 429:61-75. doi: 10.1111/ j.1749-6632.1984.tb12315.x
53. Liang J-Y, Lipscomb WN (1987) Biochemistry 26:5293-5301. doi: 10.1021/ bi00391a012
54. Miscione GP, Stenta M, Spinelli D, Anders E, Bottoni A (2007) Theor Chem Acc 118:193-201. doi: 10.1007/s00214-007-0274-x
55. Notni J, Günther W, Anders E (2007) Eur J Inorg Chem 7:985-993. doi: 10.1002/ejic.200600962
56. Notni J, Schenk S, Roth A, Plass W, Görls H, Uhlemann U, Walter A, Schmitt M, Popp J, Chatzipapadopoulos S, Emmler T, Breitzke H, Leppert J, Buntkowsky G, Kempe K, Anders E (2006) Eur J Inorg Chem 14:2783-2791. doi: 10.1002/ejic.200500948
57. Kimura E (1994) Prog Inorg Chem 41:443-491. doi: 10.1002/ 9780470166420.ch6
58. Kimura E, Koike T, Shionoya M (1997) Struct Bond 89:1-28
59. Kimura E, Shiota T, Koike T, Shiro M, Kodama M (1990) J Am Chem Soc 112:5805-5811. doi: 10.1021/ja00171a020