-
1
-
-
11944251609
-
-
and references therein
-
Carreña, M. C. Chem. Rev. 1995, 95, 1717-1760 and references therein.
-
(1995)
Chem. Rev.
, vol.95
, pp. 1717-1760
-
-
Carreña, M.C.1
-
2
-
-
0000825564
-
-
Patai, S., Rappoport, Z., Stirling, C. J. M., Eds.; John Wiley & Sons: New York
-
Anderson, K. K. In The Chemistry of Sulphones and Sulphoxides; Patai, S., Rappoport, Z., Stirling, C. J. M., Eds.; John Wiley & Sons: New York, 1988; pp 55-94.
-
(1988)
The Chemistry of Sulphones and Sulphoxides
, pp. 55-94
-
-
Anderson, K.K.1
-
4
-
-
0003649925
-
-
Patai, S., Ed.; John Wiley & Sons: New York
-
Nudelman, A. In The Chemistry of Sulphinic Acids, Esters and their Derivatives; Patai, S., Ed.; John Wiley & Sons: New York, 1990; pp 35-85.
-
(1990)
The Chemistry of Sulphinic Acids, Esters and Their Derivatives
, pp. 35-85
-
-
Nudelman, A.1
-
6
-
-
0030694323
-
-
Liu, G.; Cogan, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1997, 119, 9913-9914.
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 9913-9914
-
-
Liu, G.1
Cogan, D.A.2
Ellman, J.A.3
-
7
-
-
0037067015
-
-
Kochi, T.; Tang, T. P.; Ellman, J. A. J. Am. Chem. Soc. 2002, 124, 6518-6519.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 6518-6519
-
-
Kochi, T.1
Tang, T.P.2
Ellman, J.A.3
-
8
-
-
33751157994
-
-
Davis, F. A.; Zhou, P.; Reddy, G. V. J. Org. Chem. 1994, 59, 3243-3245.
-
(1994)
J. Org. Chem.
, vol.59
, pp. 3243-3245
-
-
Davis, F.A.1
Zhou, P.2
Reddy, G.V.3
-
11
-
-
0000131972
-
-
(b) Hulce, M.; Mallamo, J. P.; Frye, L. L.; Kogan, T. P.; Posner, G. A. Org. Synth. 1986, 64, 196-206.
-
(1986)
Org. Synth.
, vol.64
, pp. 196-206
-
-
Hulce, M.1
Mallamo, J.P.2
Frye, L.L.3
Kogan, T.P.4
Posner, G.A.5
-
12
-
-
0001922385
-
-
Patai, S., Rappoport, Z., Stirling, C. J. M., Eds.; John Wiley & Sons: New York
-
Drabowicz, J.; Kielbasinski, P.; Mikolajczyk, M. In The Chemistry of Sulphones and Sulphoxides; Patai, S., Rappoport, Z., Stirling, C. J. M., Eds.; John Wiley & Sons: New York, 1988; pp 233-378.
-
(1988)
The Chemistry of Sulphones and Sulphoxides
, pp. 233-378
-
-
Drabowicz, J.1
Kielbasinski, P.2
Mikolajczyk, M.3
-
13
-
-
0033582582
-
-
Davis, F. A.; Xhang, Y.; Andemichael, Y.; Fang, T.; Fanelli, D. L.; Zhang, H. J. Org. Chem. 1999, 64, 1403-1406.
-
(1999)
J. Org. Chem.
, vol.64
, pp. 1403-1406
-
-
Davis, F.A.1
Xhang, Y.2
Andemichael, Y.3
Fang, T.4
Fanelli, D.L.5
Zhang, H.6
-
15
-
-
0027096463
-
-
Davis, F. A.; Reddy, R. T.; Reddy, R. E. J. Org. Chem. 1992, 57, 6387-6389.
-
(1992)
J. Org. Chem.
, vol.57
, pp. 6387-6389
-
-
Davis, F.A.1
Reddy, R.T.2
Reddy, R.E.3
-
16
-
-
0032547296
-
-
Cogan, D. A.; Liu, G.; Kim, K.; Backes, B. J.; Ellman, J. A. J. Am. Chem. Soc. 1998, 120, 8011-8019.
-
(1998)
J. Am. Chem. Soc.
, vol.120
, pp. 8011-8019
-
-
Cogan, D.A.1
Liu, G.2
Kim, K.3
Backes, B.J.4
Ellman, J.A.5
-
17
-
-
0037055013
-
-
Han, Z.; Krishnamurthy, D.; Grover, P.; Fang, Q. K.; Senanayake, C. H. J. Am. Chem. Soc. 2002, 124, 7880-7881.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 7880-7881
-
-
Han, Z.1
Krishnamurthy, D.2
Grover, P.3
Fang, Q.K.4
Senanayake, C.H.5
-
20
-
-
0033368448
-
-
ten Brink, H. B.; Holland, H. L.; Schoemaker, H. E.; van Lingen, H.; Wever, R. Tetrahedron: Asymmetry 1999, 10, 4563-4572.
-
(1999)
Tetrahedron: Asymmetry
, vol.10
, pp. 4563-4572
-
-
Ten Brink, H.B.1
Holland, H.L.2
Schoemaker, H.E.3
Van Lingen, H.4
Wever, R.5
-
21
-
-
0001889898
-
-
Patai, S., Ed.; Wiley: Chichester, U.K.
-
(a) Capozzi, G.; Modena, G.; Pasquato, L. In The Chemistry of Sulphenic Acids and Their Derivatives; Patai, S., Ed.; Wiley: Chichester, U.K., 1990; pp 403-516.
-
(1990)
The Chemistry of Sulphenic Acids and Their Derivatives
, pp. 403-516
-
-
Capozzi, G.1
Modena, G.2
Pasquato, L.3
-
25
-
-
0000565931
-
-
Burgess, K.; Henderson, I.; Ho, K.-K. J. Org. Chem. 1992, 57, 1290-1295.
-
(1992)
J. Org. Chem.
, vol.57
, pp. 1290-1295
-
-
Burgess, K.1
Henderson, I.2
Ho, K.-K.3
-
27
-
-
0033597843
-
-
Backes, B. J.; Dragoli, D. R.; Ellman, J. A. J. Org. Chem. 1999, 64, 5472-5478.
-
(1999)
J. Org. Chem.
, vol.64
, pp. 5472-5478
-
-
Backes, B.J.1
Dragoli, D.R.2
Ellman, J.A.3
-
30
-
-
0005498666
-
-
(h) Gontcharov, A. V.; Liu, H.; Sharpless, K. B. Org. Lett. 1999, 1, 783-786.
-
(1999)
Org. Lett.
, vol.1
, pp. 783-786
-
-
Gontcharov, A.V.1
Liu, H.2
Sharpless, K.B.3
-
31
-
-
0031796722
-
-
Janes, L. E.; Löwendahl, C. P.; Kazlauskas, R. J. Chem.-Eur. J. 1998, 4, 2324-2331.
-
(1998)
Chem.-Eur. J.
, vol.4
, pp. 2324-2331
-
-
Janes, L.E.1
Löwendahl, C.P.2
Kazlauskas, R.J.3
-
32
-
-
13944265128
-
-
Roberts, S. M., Ed.; John Wiley & Sons: New York
-
A computer program, Selectivity-KRESH, was used for all calculations. For details, see: Faber, K.; Hönig, H.; Kleewein, A. In Preparative Biotransformations; Roberts, S. M., Ed.; John Wiley & Sons: New York, 1995; pp 0.079-0.084.
-
(1995)
Preparative Biotransformations
-
-
Faber, K.1
Hönig, H.2
Kleewein, A.3
-
33
-
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13944268402
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-
Manuscript in preparation
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1H NMR and HRMS-EI identified p-toluenesulfinic acid as the primary product in this enzymatic reaction: Mugford, P. F.; Magloire, V. P.; Kazlauskas, R. J. Manuscript in preparation.
-
-
-
Mugford, P.F.1
Magloire, V.P.2
Kazlauskas, R.J.3
-
34
-
-
0024502971
-
-
(a) Park, S.-S.; Wong, S.-L.; Wang, L.-F.; Doi, R. H. J. Bacteriol. 1989, 171, 2657-2665.
-
(1989)
J. Bacteriol.
, vol.171
, pp. 2657-2665
-
-
Park, S.-S.1
Wong, S.-L.2
Wang, L.-F.3
Doi, R.H.4
-
36
-
-
0032553556
-
-
Jain, S. C.; Shinde, U.; Li, Y.; Inouye, M.; Berman, H. M. J. Mol. Biol. 1998, 284, 137-144.
-
(1998)
J. Mol. Biol.
, vol.284
, pp. 137-144
-
-
Jain, S.C.1
Shinde, U.2
Li, Y.3
Inouye, M.4
Berman, H.M.5
-
37
-
-
13944276054
-
-
note
-
Based on a limit of detection of 0.1%.
-
-
-
-
38
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-
0022445901
-
-
(a) Estell, D. A.; Graycar, T. P.; Miller, J. V.; Powers, D. B.; Burnier, J. P.; Ng, P. G.; Wells, J. A. Science 1986, 233, 659-663.
-
(1986)
Science
, vol.233
, pp. 659-663
-
-
Estell, D.A.1
Graycar, T.P.2
Miller, J.V.3
Powers, D.B.4
Burnier, J.P.5
Ng, P.G.6
Wells, J.A.7
-
39
-
-
0001463338
-
-
(b) Wells, J. A.; Powers, D. B.; Bott, R. R.; Graycar, T. P.; Estell, D. A. Proc. Natl. Acad. Sci. U.S.A. 1987, 84, 1219-1223.
-
(1987)
Proc. Natl. Acad. Sci. U.S.A.
, vol.84
, pp. 1219-1223
-
-
Wells, J.A.1
Powers, D.B.2
Bott, R.R.3
Graycar, T.P.4
Estell, D.A.5
-
40
-
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13944262275
-
-
note
-
app = 52%) after 6 h. This enzyme was missed in our initial activity screen because it reacted only slowly with the N-chloroacetyl derivative 1c.
-
-
-
-
41
-
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13944273882
-
-
note
-
The solubility of both 5h and 6h in 10% MeCN/buffer was <5 mM. Organic cosolvents (1,4-dioxane, EtOH, DMSO) or additives (10 mM guanidium chloride) did not significantly improve solubility. Performing the reaction experiment at 50 °C or using a biphasic reaction system with tert-butylmethyl ether also did not increase conversion. Using MeCN or 1.4-dioxane at higher concentrations (20-90%) improved substrate solubility, but did not increase conversion.
-
-
-
-
42
-
-
0037078849
-
-
Han, Z.; Krishnamurthy, D.; Pflum, D.; Grover, P.; Wald, S. A.; Senanayake, C. H. Org. Lett. 2002, 4, 4025-4028.
-
(2002)
Org. Lett.
, vol.4
, pp. 4025-4028
-
-
Han, Z.1
Krishnamurthy, D.2
Pflum, D.3
Grover, P.4
Wald, S.A.5
Senanayake, C.H.6
-
43
-
-
0018235994
-
-
Keith, D. D.; Tortora, J. A.; Yang, R. J. Org. Chem. 1978, 43, 3711-3713.
-
(1978)
J. Org. Chem.
, vol.43
, pp. 3711-3713
-
-
Keith, D.D.1
Tortora, J.A.2
Yang, R.3
-
44
-
-
13944251103
-
-
note
-
3 was used in place of sodium bis(trimethylsilyl) amide. (R)-5 formed in low yield (3%) and enantiomeric excess (68% ee).
-
-
-
-
46
-
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33749000228
-
-
(a) Fujita, T.; Iwasa, J.; Hansch, C. J. Am. Chem. Soc. 1964, 86, 5175-5180.
-
(1964)
J. Am. Chem. Soc.
, vol.86
, pp. 5175-5180
-
-
Fujita, T.1
Iwasa, J.2
Hansch, C.3
-
47
-
-
8644243613
-
-
(b) Leo, A.; Hansch, C.; Elkins, D. Chem. Rev. 1971, 71, 525-616.
-
(1971)
Chem. Rev.
, vol.71
, pp. 525-616
-
-
Leo, A.1
Hansch, C.2
Elkins, D.3
-
51
-
-
13944261337
-
-
note
-
1 pocket lies on the surface of the protein and the benzyl group is not completely buried, we estimate the energy for this hydrophobic interaction to be 2.7-5.5 kcal/mol.36a,b,37
-
-
-
-
52
-
-
20544433165
-
-
Estimated from the van der Waals radii of chlorine (1.75 Å) and hydrogen (1.20 Å) and the O-H bond length (0.96 Å) from: Bondi, A. J. Phys. Chem. 1964, 68, 441-451.
-
(1964)
J. Phys. Chem.
, vol.68
, pp. 441-451
-
-
Bondi, A.1
-
54
-
-
13944275352
-
-
note
-
Removal of a hydrogen bond donor or acceptor in an enzyme active site weakens binding by 0.5-1.5 kcal/mol.37 Although the hydrogen bond inventory is zero (i.e., the number of hydrogen bonds is the same for both the free enzyme and the enzyme-substrate complex), hydrogen bonds between an enzyme and substrate increase the entropy due to the release of bound water molecules.
-
-
-
-
55
-
-
13944262979
-
-
note
-
M values for 1h and 1c than for 1a, but low solubility of these substrates (<5 mM) prevented us from testing this prediction.
-
-
-
-
58
-
-
13944282338
-
-
note
-
1′ pocket.
-
-
-
-
59
-
-
0036537789
-
-
Bharatam, P. V.; Kaur, A.; Kaur, D. J. Phys. Org. Chem. 2002, 15, 197-203.
-
(2002)
J. Phys. Org. Chem.
, vol.15
, pp. 197-203
-
-
Bharatam, P.V.1
Kaur, A.2
Kaur, D.3
-
60
-
-
0028997772
-
-
Rossi, K. A.; Merz, K. M., Jr.; Smith, G. M.; Baldwin, J. J. J. Med. Chem. 1995, 38, 2061-2069.
-
(1995)
J. Med. Chem.
, vol.38
, pp. 2061-2069
-
-
Rossi, K.A.1
Merz Jr., K.M.2
Smith, G.M.3
Baldwin, J.J.4
-
61
-
-
13944273129
-
-
note
-
See Supporting Information for complete molecular modeling details.
-
-
-
-
62
-
-
0033578652
-
-
(a) Braunegg, G.; de Raadt, A.; Feichtenhofer, S.; Griengl, H.; Kopper, I.; Lehman, A.; Weber, H.-J. Angew. Chem., Int. Ed. 1999, 38, 2763-2766.
-
(1999)
Angew. Chem., Int. Ed.
, vol.38
, pp. 2763-2766
-
-
Braunegg, G.1
De Raadt, A.2
Feichtenhofer, S.3
Griengl, H.4
Kopper, I.5
Lehman, A.6
Weber, H.-J.7
-
63
-
-
0035808421
-
-
(b) de Raadt, A.; Griengl, H.; Weber, H. Chem.-Eur. J. 2001, 7, 27-31.
-
(2001)
Chem.-Eur. J.
, vol.7
, pp. 27-31
-
-
De Raadt, A.1
Griengl, H.2
Weber, H.3
-
65
-
-
0029969716
-
-
Ema, T.; Maeno, S.; Takaya, Y.; Sakai, T.; Utaka, M. J. Org. Chem. 1996, 61, 8610-8616.
-
(1996)
J. Org. Chem.
, vol.61
, pp. 8610-8616
-
-
Ema, T.1
Maeno, S.2
Takaya, Y.3
Sakai, T.4
Utaka, M.5
-
67
-
-
0001323502
-
-
(b) Margolin, A. L.; Tai, D.-F.; Klibanov, A. M. J. Am. Chem. Soc. 1987, 109, 7885-7887.
-
(1987)
J. Am. Chem. Soc.
, vol.109
, pp. 7885-7887
-
-
Margolin, A.L.1
Tai, D.-F.2
Klibanov, A.M.3
-
68
-
-
0000858214
-
-
Sakurai, T.; Margolin, A. L.; Russell, A. J.; Klibanov, A. M. J. Am. Chem. Soc. 1988, 110, 7236-7237.
-
(1988)
J. Am. Chem. Soc.
, vol.110
, pp. 7236-7237
-
-
Sakurai, T.1
Margolin, A.L.2
Russell, A.J.3
Klibanov, A.M.4
-
70
-
-
85011164531
-
-
Chen, F. M. F.; Kuroda, K.; Benoiton, N. L. Synthesis 1978, 12, 928-930.
-
(1978)
Synthesis
, vol.12
, pp. 928-930
-
-
Chen, F.M.F.1
Kuroda, K.2
Benoiton, N.L.3
-
72
-
-
0021757436
-
-
(a) Weiner, S. J.; Kollman, P. A.; Case, D. A.; Singh, U. C.; Ghio, C.; Alagona, G.; Profeta, S.; Weiner, P. J. Am. Chem. Soc. 1984, 106, 765-784.
-
(1984)
J. Am. Chem. Soc.
, vol.106
, pp. 765-784
-
-
Weiner, S.J.1
Kollman, P.A.2
Case, D.A.3
Singh, U.C.4
Ghio, C.5
Alagona, G.6
Profeta, S.7
Weiner, P.8
-
73
-
-
84988053694
-
-
(b) Weiner, S. J.; Kollman, P. A.; Nguyen, D. T.; Case, D. A. J. Comput. Chem. 1986, 7, 230-252.
-
(1986)
J. Comput. Chem.
, vol.7
, pp. 230-252
-
-
Weiner, S.J.1
Kollman, P.A.2
Nguyen, D.T.3
Case, D.A.4
-
74
-
-
0035101120
-
-
Raza, S.; Fransson, L.; Hult, K. Protein Sci. 2001, 10, 329-338.
-
(2001)
Protein Sci.
, vol.10
, pp. 329-338
-
-
Raza, S.1
Fransson, L.2
Hult, K.3
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