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Organic and Biomolecular Chemistry

Volumn 10, Issue 40, 2012, Pages 8095-8101

Kinetic and computational evidence for an intermediate in the hydrolysis of sulfonate esters

(4) Babtie, Ann C a Lima, Marcelo F a,b Kirby, Anthony J a Hollfelder, Florian a

a UNIVERSITY OF CAMBRIDGE (United Kingdom)

b FEDERAL UNIVERSITY OF MATO GROSSO (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALINE HYDROLYSIS; BENZENESULFONATES; BREAKPOINT; COMBINED EFFECT; CONCERTED MECHANISM; CONCERTED REACTIONS; HYDROLYTIC REACTIONS; LEAVING GROUPS; QM/MM CALCULATIONS; SULFONATE ESTERS; TWO-STEP MECHANISMS;

ESTERIFICATION; HYDROLYSIS;

ESTERS;

BENZENESULFONIC ACID; BENZENESULFONIC ACID DERIVATIVE; ESTER; HYDROXIDE; POTASSIUM DERIVATIVE; POTASSIUM HYDROXIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; HYDROLYSIS; KINETICS; QUANTUM THEORY; THERMODYNAMICS;

BENZENESULFONATES; ESTERS; HYDROLYSIS; HYDROXIDES; KINETICS; MOLECULAR STRUCTURE; POTASSIUM COMPOUNDS; QUANTUM THEORY; THERMODYNAMICS;

EID: 84866936426 PISSN: 14770520 EISSN: None Source Type: Journal
DOI: 10.1039/c2ob25699a Document Type: Article

Times cited : (16)

References (62)

1
- 33748591572
- W. W. Cleland A. C. Hengge Chem. Rev. 2006 106 3252 3278
- (2006) Chem. Rev. , vol.106 , pp. 3252-3278
- Cleland, W.W.¹ Hengge, A.C.²

2
- 0034014055
- J. W. Kehoe C. R. Bertozzi Chem. Biol. 2000 7 R57 R61
- (2000) Chem. Biol. , vol.7
- Kehoe, J.W.¹ Bertozzi, C.R.²

3
- 8844275956
- S. R. Hanson M. D. Best C. H. Wong Angew. Chem., Int. Ed. 2004 43 5736 5763
- (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 5736-5763
- Hanson, S.R.¹ Best, M.D.² Wong, C.H.³

4
- 0033117461
- P. J. O'Brian D. Herschlag Chem. Biol. 1999 6 R91 R105
- (1999) Chem. Biol. , vol.6
- O'Brian, P.J.¹ Herschlag, D.²

5
- 77953623874
- O. Khersonsky D. S. Tawfik Annu. Rev. Biochem. 2011 79 471 505
- (2011) Annu. Rev. Biochem. , vol.79 , pp. 471-505
- Khersonsky, O.¹ Tawfik, D.S.²

6
- 77949880028
- A. C. Babtie N. Tokuriki F. Hollfelder Curr. Opin. Chem. Biol. 2010 14 200 207
- (2010) Curr. Opin. Chem. Biol. , vol.14 , pp. 200-207
- Babtie, A.C.¹ Tokuriki, N.² Hollfelder, F.³

7
- 65449177658
- S. Jonas F. Hollfelder Pure Appl. Chem. 2009 81 731 742
- (2009) Pure Appl. Chem. , vol.81 , pp. 731-742
- Jonas, S.¹ Hollfelder, F.²

8
- 84891742853
- M. F. Mohamed F. Hollfelder Biochim. Biophys. Acta, Proteins Proteomics 2012
- (2012) Biochim. Biophys. Acta, Proteins Proteomics
- Mohamed, M.F.¹ Hollfelder, F.²

9
- 54249126236
- ed. U. T. Bornscheuer and S. Lutz, Wiley-VCH, Chichester
- S. Jonas and F. Hollfelder, in The Handbook of Protein Engineering, ed., U. T. Bornscheuer, and, S. Lutz, Wiley-VCH, Chichester, 2008, vol. 1, pp. 47-72
- (2008) The Handbook of Protein Engineering , vol.1 , pp. 47-72
- Jonas, S.¹ Hollfelder, F.²

10
- 54249084848
- S. Jonas B. van Loo M. Hyvonen F. Hollfelder J. Mol. Biol. 2008 384 120 136
- (2008) J. Mol. Biol. , vol.384 , pp. 120-136
- Jonas, S.¹ Van Loo, B.² Hyvonen, M.³ Hollfelder, F.⁴

11
- 31944441501
- J. Zalatan D. Herschlag J. Am. Chem. Soc. 2006 128 1293 1303
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 1293-1303
- Zalatan, J.¹ Herschlag, D.²

12
- 56949087215
- J. Zalatan T. Fenn D. Herschlag J. Mol. Biol. 2008 384 1174 1189
- (2008) J. Mol. Biol. , vol.384 , pp. 1174-1189
- Zalatan, J.¹ Fenn, T.² Herschlag, D.³

13
- 0032477286
- P. J. O'Brien D. Herschlag J. Am. Chem. Soc. 1998 120 12369 12370
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 12369-12370
- O'Brien, P.J.¹ Herschlag, D.²

14
- 0035873714
- P. J. O'Brien D. Herschlag Biochemistry 2001 40 5691 5699
- (2001) Biochemistry , vol.40 , pp. 5691-5699
- O'Brien, P.J.¹ Herschlag, D.²

15
- 77649239492
- B. van Loo S. Jonas A. C. Babtie A. Benjdia O. Berteau M. Hyvonen F. Hollfelder Proc. Natl. Acad. Sci. U. S. A. 2010 107 2740 2745
- (2010) Proc. Natl. Acad. Sci. U. S. A. , vol.107 , pp. 2740-2745
- Van Loo, B.¹ Jonas, S.² Babtie, A.C.³ Benjdia, A.⁴ Berteau, O.⁵ Hyvonen, M.⁶ Hollfelder, F.⁷

16
- 54249149606
- L. F. Olguin S. E. Askew A. C. O'Donoghue F. Hollfelder J. Am. Chem. Soc. 2008 130 16547 16555
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 16547-16555
- Olguin, L.F.¹ Askew, S.E.² O'Donoghue, A.C.³ Hollfelder, F.⁴

17
- 70349974741
- A. C. Babtie S. Bandyopadhyay L. F. Olguin F. Hollfelder Angew. Chem., Int. Ed. 2009 48 3692 3694
- (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 3692-3694
- Babtie, A.C.¹ Bandyopadhyay, S.² Olguin, L.F.³ Hollfelder, F.⁴

18
- 0034010828
- M. A. Kertesz FEMS Microbiol. Rev. 2000 24 135 175
- (2000) FEMS Microbiol. Rev. , vol.24 , pp. 135-175
- Kertesz, M.A.¹

19
- 0034927394
- J. R. van der Ploeg E. Eichhorn T. Leisinger Arch. Microbiol. 2001 176 1 8
- (2001) Arch. Microbiol. , vol.176 , pp. 1-8
- Van Der Ploeg, J.R.¹ Eichhorn, E.² Leisinger, T.³

20
- 0000894629
- S. Ba-Saif M. Waring A. Williams J. Am. Chem. Soc. 1990 112 8115 8120
- (1990) J. Am. Chem. Soc. , vol.112 , pp. 8115-8120
- Ba-Saif, S.¹ Waring, M.² Williams, A.³

21
- 37049066925
- S. Ba-Saif M. Waring A. Williams J. Chem. Soc., Perkin Trans. 2 1991 1991 1653 1659
- (1991) J. Chem. Soc., Perkin Trans. 2 , vol.1991 , pp. 1653-1659
- Ba-Saif, S.¹ Waring, M.² Williams, A.³

22
- 33847394326
- S. J. Benkovic P. A. Benkovic J. Am. Chem. Soc. 1966 88 5504 5511
- (1966) J. Am. Chem. Soc. , vol.88 , pp. 5504-5511
- Benkovic, S.J.¹ Benkovic, P.A.²

23
- 33845921520
- S. A. Khan A. J. Kirby J. Chem. Soc. B 1970 1172 1182
- (1970) J. Chem. Soc. B , pp. 1172-1182
- Khan, S.A.¹ Kirby, A.J.²

24
- 0000443933
- A. J. Kirby W. P. Jencks J. Am. Chem. Soc. 1965 87 3209
- (1965) J. Am. Chem. Soc. , vol.87 , pp. 3209
- Kirby, A.J.¹ Jencks, W.P.²

25
- 0000313137
- A. J. Kirby W. P. Jencks J. Am. Chem. Soc. 1965 87 3217
- (1965) J. Am. Chem. Soc. , vol.87 , pp. 3217
- Kirby, A.J.¹ Jencks, W.P.²

26
- 37049122234
- A. J. Kirby M. Younas J. Chem. Soc. B 1970 1165 1172
- (1970) J. Chem. Soc. B , pp. 1165-1172
- Kirby, A.J.¹ Younas, M.²

27
- 37049128024
- A. J. Kirby M. Younas J. Chem. Soc. B 1970 510 513
- (1970) J. Chem. Soc. B , pp. 510-513
- Kirby, A.J.¹ Younas, M.²

28
- 84855649802
- D. R. Edwards D. C. Lohman R. Wolfenden J. Am. Chem. Soc. 2012 134 525 531
- (2012) J. Am. Chem. Soc. , vol.134 , pp. 525-531
- Edwards, D.R.¹ Lohman, D.C.² Wolfenden, R.³

29
- 0242585345
- S. D. Lahiri G. Zhang D. Dunaway-Mariano K. N. Allen Science 2003 299 2067 2071
- (2003) Science , vol.299 , pp. 2067-2071
- Lahiri, S.D.¹ Zhang, G.² Dunaway-Mariano, D.³ Allen, K.N.⁴

30
- 77949537262
- N. J. Baxter M. W. Bowler T. Alizadeh M. J. Cliff A. M. Hounslow B. Wu D. B. Berkowitz N. H. Williams G. M. Blackburn J. P. Waltho Proc. Natl. Acad. Sci. U. S. A. 2010 107 4555 4560
- (2010) Proc. Natl. Acad. Sci. U. S. A. , vol.107 , pp. 4555-4560
- Baxter, N.J.¹ Bowler, M.W.² Alizadeh, T.³ Cliff, M.J.⁴ Hounslow, A.M.⁵ Wu, B.⁶ Berkowitz, D.B.⁷ Williams, N.H.⁸ Blackburn, G.M.⁹ Waltho, J.P.¹⁰

31
- 70450177317
- N. J. Baxter A. M. Hounslow M. W. Bowler N. H. Williams G. M. Blackburn J. P. Waltho J. Am. Chem. Soc. 2009 131 16334 16335
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 16334-16335
- Baxter, N.J.¹ Hounslow, A.M.² Bowler, M.W.³ Williams, N.H.⁴ Blackburn, G.M.⁵ Waltho, J.P.⁶

32
- 33749525674
- N. J. Baxter L. F. Olguin M. Golicnik G. Feng A. M. Hounslow W. Bermel G. M. Blackburn F. Hollfelder J. P. Waltho N. H. Williams Proc. Natl. Acad. Sci. U. S. A. 2006 103 14732 14737
- (2006) Proc. Natl. Acad. Sci. U. S. A. , vol.103 , pp. 14732-14737
- Baxter, N.J.¹ Olguin, L.F.² Golicnik, M.³ Feng, G.⁴ Hounslow, A.M.⁵ Bermel, W.⁶ Blackburn, G.M.⁷ Hollfelder, F.⁸ Waltho, J.P.⁹ Williams, N.H.¹⁰

33
- 63149188672
- M. Golicnik L. F. Olguin G. Feng N. J. Baxter J. P. Waltho N. H. Williams F. Hollfelder J. Am. Chem. Soc. 2009 131 1575 1588
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 1575-1588
- Golicnik, M.¹ Olguin, L.F.² Feng, G.³ Baxter, N.J.⁴ Waltho, J.P.⁵ Williams, N.H.⁶ Hollfelder, F.⁷

34
- 33847089840
- C. R. Farrar A. Williams J. Am. Chem. Soc. 1977 99 1912 1915
- (1977) J. Am. Chem. Soc. , vol.99 , pp. 1912-1915
- Farrar, C.R.¹ Williams, A.²

35
- 33947092548
- T. Deacon C. Farrar B. Sikkel A. Williams J. Am. Chem. Soc. 1978 100 2525 2534
- (1978) J. Am. Chem. Soc. , vol.100 , pp. 2525-2534
- Deacon, T.¹ Farrar, C.² Sikkel, B.³ Williams, A.⁴

36
- 0001316312
- S. Thea G. Cevasco G. Guanti A. Hopkins N. Kashefinaini A. Williams J. Org. Chem. 1985 50 2158 2165
- (1985) J. Org. Chem. , vol.50 , pp. 2158-2165
- Thea, S.¹ Cevasco, G.² Guanti, G.³ Hopkins, A.⁴ Kashefinaini, N.⁵ Williams, A.⁶

37
- 0000804085
- I. M. Gordon H. Maskill M. F. Ruasse Chem. Soc. Rev. 1989 18 123 151
- (1989) Chem. Soc. Rev. , vol.18 , pp. 123-151
- Gordon, I.M.¹ Maskill, H.² Ruasse, M.F.³

38
- 0000104135
- P. D'Rozario R. L. Smyth A. Williams J. Am. Chem. Soc. 1984 106 5027 5028
- (1984) J. Am. Chem. Soc. , vol.106 , pp. 5027-5028
- D'Rozario, P.¹ Smyth, R.L.² Williams, A.³

39
- 2442709028
- M. I. Page Acc. Chem. Res. 2004 37 297 303
- (2004) Acc. Chem. Res. , vol.37 , pp. 297-303
- Page, M.I.¹

40
- 0034640055
- N. J. Baxter L. J. M. Rigoreau A. P. Laws M. I. Page J. Am. Chem. Soc. 2000 122 3375 3385
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 3375-3385
- Baxter, N.J.¹ Rigoreau, L.J.M.² Laws, A.P.³ Page, M.I.⁴

41
- 0002805053
- N. J. Baxter A. P. Laws L. Rigoreau M. I. Page Chem. Commun. 1997 2037 2038
- (1997) Chem. Commun. , pp. 2037-2038
- Baxter, N.J.¹ Laws, A.P.² Rigoreau, L.³ Page, M.I.⁴

42
- 84961977626
- I. R. Greig Chem. Soc. Rev. 2010 39 2272 2301
- (2010) Chem. Soc. Rev. , vol.39 , pp. 2272-2301
- Greig, I.R.¹

43
- 4344686076
- Royal Society of Chemistry, Cambridge
- A. Williams, Free Energy Relationships in Organic and Bio-Organic Chemistry, Royal Society of Chemistry, Cambridge, 2003
- (2003) Free Energy Relationships in Organic and Bio-Organic Chemistry
- Williams, A.¹

44
- 2942739267
- N. H. Williams M. Padovani P. Wyman J. Phys. Org. Chem. 2004 17 472 477
- (2004) J. Phys. Org. Chem. , vol.17 , pp. 472-477
- Williams, N.H.¹ Padovani, M.² Wyman, P.³

45
- 4344672759
- H. Lonnberg R. Stromberg A. Williams Org. Biomol. Chem. 2004 2 2165 2167
- (2004) Org. Biomol. Chem. , vol.2 , pp. 2165-2167
- Lonnberg, H.¹ Stromberg, R.² Williams, A.³

46
- 37049139718
- E. A. Castro R. B. Moodie J. Chem. Soc., Chem. Commun. 1973 828 829
- (1973) J. Chem. Soc., Chem. Commun. , pp. 828-829
- Castro, E.A.¹ Moodie, R.B.²

47
- 34548456894
- I.-H. Um K. Akhtar Y.-M. Park S. B. Khan Bull. Korean Chem. Soc. 2007 28 1353 1357
- (2007) Bull. Korean Chem. Soc. , vol.28 , pp. 1353-1357
- Um, I.-H.¹ Akhtar, K.² Park, Y.-M.³ Khan, S.B.⁴

48
- 84891737745
- P. M. Bond E. A. Castro R. B. Moodie J. Chem. Soc., Perkin Trans. 2 1968 69 72
- (1968) J. Chem. Soc., Perkin Trans. 2 , pp. 69-72
- Bond, P.M.¹ Castro, E.A.² Moodie, R.B.³

49
- 84962428822
- H. Li M. S. Gordon J. Chem. Phys. 2007 126 124112
- (2007) J. Chem. Phys. , vol.126 , pp. 124112
- Li, H.¹ Gordon, M.S.²

50
- 0038391194
- Effective Fragment Method for Modeling Intermolecular Hydrogen Bonding effects on Quantum Mechanical Calculations
- ed. D. A. Smith, ACS, Washington, DC
- J. H. Jensen, P. N. Day, M. S. Gordon, H. Basch, D. Cohen, D. R. Garmer, M. Krauss and W. J. Stevens, Effective Fragment Method for Modeling Intermolecular Hydrogen Bonding effects on Quantum Mechanical Calculations, in ACS Symposium Series, ed., D. A. Smith, ACS, Washington, DC, 1994, vol. 569, pp. 139-151
- (1994) ACS Symposium Series , vol.569 , pp. 139-151
- Jensen, J.H.¹ Day, P.N.² Gordon, M.S.³ Basch, H.⁴ Cohen, D.⁵ Garmer, D.R.⁶ Krauss, M.⁷ Stevens, W.J.⁸

51
- 84961985847
- V. Barone M. Cossi J. Phys. Chem. A 1998 102 1995 2001
- (1998) J. Phys. Chem. A , vol.102 , pp. 1995-2001
- Barone, V.¹ Cossi, M.²

52
- 0035138053
- M. S. Gordon M. A. Freitag P. Bandyopadhyay J. H. Jensen V. Kairys W. J. Stevens J. Phys. Chem. A 2001 105 293 307
- (2001) J. Phys. Chem. A , vol.105 , pp. 293-307
- Gordon, M.S.¹ Freitag, M.A.² Bandyopadhyay, P.³ Jensen, J.H.⁴ Kairys, V.⁵ Stevens, W.J.⁶

53
- 56249120958
- Y. Peng Z. Deng S. Lang Y. Fan J. Chem. Res. 2008 63 555
- (2008) J. Chem. Res. , vol.63 , pp. 555
- Peng, Y.¹ Deng, Z.² Lang, S.³ Fan, Y.⁴

54
- 34547751907
- M. Vembu H. A. Sparkes J. A. K. Howard Acta Crystallogr., Sect. E: Struct. Rep. Online 2007 63 o3545
- (2007) Acta Crystallogr., Sect. E: Struct. Rep. Online , vol.63 , pp. 3545
- Vembu, M.¹ Sparkes, H.A.² Howard, J.A.K.³

55
- 34547761320
- M. Vembu H. A. Sparkes J. A. K. Howard Acta Crystallogr., Sect. E: Struct. Rep. Online 2007 63 o3543
- (2007) Acta Crystallogr., Sect. E: Struct. Rep. Online , vol.63 , pp. 3543
- Vembu, M.¹ Sparkes, H.A.² Howard, J.A.K.³

56
- 33750009842
- L. Wu F.-X. Liang W. Q. Zhang Acta Crystallogr., Sect. E: Struct. Rep. Online 2006 62 o4288 o4290
- (2006) Acta Crystallogr., Sect. E: Struct. Rep. Online , vol.62
- Wu, L.¹ Liang, F.-X.² Zhang, W.Q.³

57
- 34547813674
- M. Vembu H. A. Sparkes J. A. K. Howard Acta Crystallogr., Sect. E: Struct. Rep. Online 2007 63 o3544
- (2007) Acta Crystallogr., Sect. E: Struct. Rep. Online , vol.63 , pp. 3544
- Vembu, M.¹ Sparkes, H.A.² Howard, J.A.K.³

58
- 73749084980
- N. Tarrat J. Mol. Struct. (THEOCHEM) 2010 941 56 60
- (2010) J. Mol. Struct. (THEOCHEM) , vol.941 , pp. 56-60
- Tarrat, N.¹

59
- 0004205267
- Portland Press Ltd, London, UK, 3 edn
- A. Cornish-Bowden, Fundamentals of Enzyme Kinetics, Portland Press Ltd, London, UK, 3 edn, 2004
- (2004) Fundamentals of Enzyme Kinetics
- Cornish-Bowden, A.¹

60
- 0003920544
- ed. G. D. Fasman, CRC, 3rd edn
- W. P. Jencks and J. Regenstein, in Handbook of Biochemistry and Molecular Biology, ed., G. D. Fasman, CRC, 3rd edn, 1976, vol. 1, p. 314
- (1976) Handbook of Biochemistry and Molecular Biology , vol.1 , pp. 314
- Jencks, W.P.¹ Regenstein, J.²

61
- 84893169025
- M. W. Schmidt K. K. Baldridge J. A. Boatz S. T. Elbert M. S. Gordon J. H. Jensen S. Koseki N. Matsunaga K. A. Nguyen S. J. Su T. L. Windus M. Dupuis J. A. Montgomery J. Comput. Chem. 1993 14 1347 1363
- (1993) J. Comput. Chem. , vol.14 , pp. 1347-1363
- Schmidt, M.W.¹ Baldridge, K.K.² Boatz, J.A.³ Elbert, S.T.⁴ Gordon, M.S.⁵ Jensen, J.H.⁶ Koseki, S.⁷ Matsunaga, N.⁸ Nguyen, K.A.⁹ Su, S.J.¹⁰ Windus, T.L.¹¹ Dupuis, M.¹² Montgomery, J.A.¹³

62
- 0035138053
- M. S. Gordon M. S. Freitag P. Bandyopadhyay J. H. Jensen V. Kairys W. J. Stevens J. Phys. Chem. A 2001 105 293 307
- (2001) J. Phys. Chem. A , vol.105 , pp. 293-307
- Gordon, M.S.¹ Freitag, M.S.² Bandyopadhyay, P.³ Jensen, J.H.⁴ Kairys, V.⁵ Stevens, W.J.⁶

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