-
2
-
-
0003460893
-
-
M. Dekker: New York
-
Sheldon, R. A. Chirotechnology: Industrial Synthesis of Optically Active Compounds; M. Dekker: New York, 1993. Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Pergamon Press: Oxford, 1994. Drauz, K.; Waldmann, H. Enzyme Catalysis in Organic Synthesis, 2nd ed.; Springer-Verlag: Berlin, 1996. Zaks, A.; Dodds, D. R. Drug Dev. Trends 1997, 2, 513-531. Faber, K. Biotransformations in Organic Chemistry, 3rd ed.; Springer-Verlag: Berlin, 1997.
-
(1993)
Chirotechnology: Industrial Synthesis of Optically Active Compounds
-
-
Sheldon, R.A.1
-
3
-
-
0003458662
-
-
Pergamon Press: Oxford
-
Sheldon, R. A. Chirotechnology: Industrial Synthesis of Optically Active Compounds; M. Dekker: New York, 1993. Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Pergamon Press: Oxford, 1994. Drauz, K.; Waldmann, H. Enzyme Catalysis in Organic Synthesis, 2nd ed.; Springer-Verlag: Berlin, 1996. Zaks, A.; Dodds, D. R. Drug Dev. Trends 1997, 2, 513-531. Faber, K. Biotransformations in Organic Chemistry, 3rd ed.; Springer-Verlag: Berlin, 1997.
-
(1994)
Enzymes in Synthetic Organic Chemistry
-
-
Wong, C.-H.1
Whitesides, G.M.2
-
4
-
-
0003458664
-
-
Springer-Verlag: Berlin
-
Sheldon, R. A. Chirotechnology: Industrial Synthesis of Optically Active Compounds; M. Dekker: New York, 1993. Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Pergamon Press: Oxford, 1994. Drauz, K.; Waldmann, H. Enzyme Catalysis in Organic Synthesis, 2nd ed.; Springer-Verlag: Berlin, 1996. Zaks, A.; Dodds, D. R. Drug Dev. Trends 1997, 2, 513-531. Faber, K. Biotransformations in Organic Chemistry, 3rd ed.; Springer-Verlag: Berlin, 1997.
-
(1996)
Enzyme Catalysis in Organic Synthesis, 2nd Ed.
-
-
Drauz, K.1
Waldmann, H.2
-
5
-
-
0030785388
-
-
Sheldon, R. A. Chirotechnology: Industrial Synthesis of Optically Active Compounds; M. Dekker: New York, 1993. Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Pergamon Press: Oxford, 1994. Drauz, K.; Waldmann, H. Enzyme Catalysis in Organic Synthesis, 2nd ed.; Springer-Verlag: Berlin, 1996. Zaks, A.; Dodds, D. R. Drug Dev. Trends 1997, 2, 513-531. Faber, K. Biotransformations in Organic Chemistry, 3rd ed.; Springer-Verlag: Berlin, 1997.
-
(1997)
Drug Dev. Trends
, vol.2
, pp. 513-531
-
-
Zaks, A.1
Dodds, D.R.2
-
6
-
-
0003479152
-
-
Springer-Verlag: Berlin
-
Sheldon, R. A. Chirotechnology: Industrial Synthesis of Optically Active Compounds; M. Dekker: New York, 1993. Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Pergamon Press: Oxford, 1994. Drauz, K.; Waldmann, H. Enzyme Catalysis in Organic Synthesis, 2nd ed.; Springer-Verlag: Berlin, 1996. Zaks, A.; Dodds, D. R. Drug Dev. Trends 1997, 2, 513-531. Faber, K. Biotransformations in Organic Chemistry, 3rd ed.; Springer-Verlag: Berlin, 1997.
-
(1997)
Biotransformations in Organic Chemistry, 3rd Ed.
-
-
Faber, K.1
-
7
-
-
0027138526
-
-
Faber, K.; Ottolina, G.; Riva, S. Biocatalysis 1993, 8, 91-132.
-
(1993)
Biocatalysis
, vol.8
, pp. 91-132
-
-
Faber, K.1
Ottolina, G.2
Riva, S.3
-
9
-
-
84990106353
-
-
Chen, C.-S.; Sih, C. J. Angew. Chem., Ind. Ed. Engl. 1989, 28, 695-707. Hult, K.; Norin, T. Pure Appl. Chem. 1992, 64, 1129-1134.
-
(1989)
Angew. Chem., Ind. Ed. Engl.
, vol.28
, pp. 695-707
-
-
Chen, C.-S.1
Sih, C.J.2
-
10
-
-
0013357463
-
-
Chen, C.-S.; Sih, C. J. Angew. Chem., Ind. Ed. Engl. 1989, 28, 695-707. Hult, K.; Norin, T. Pure Appl. Chem. 1992, 64, 1129-1134.
-
(1992)
Pure Appl. Chem.
, vol.64
, pp. 1129-1134
-
-
Hult, K.1
Norin, T.2
-
13
-
-
0028302684
-
-
Wescott, C. R.; Klibanov, A. M. Biochim. Biophys. Acta 1994, 1206, 1-9. Carrea, G.; Ottolina, G.; Riva, S. Trends Biotechnol. 1995, 13, 63-70. Wescott, C. R.; Noritomi, H.; Klibanov, A. M. J. Am. Chem. Soc. 1996, 118, 10365-10370.
-
(1994)
Biochim. Biophys. Acta
, vol.1206
, pp. 1-9
-
-
Wescott, C.R.1
Klibanov, A.M.2
-
14
-
-
0028855057
-
-
Wescott, C. R.; Klibanov, A. M. Biochim. Biophys. Acta 1994, 1206, 1-9. Carrea, G.; Ottolina, G.; Riva, S. Trends Biotechnol. 1995, 13, 63-70. Wescott, C. R.; Noritomi, H.; Klibanov, A. M. J. Am. Chem. Soc. 1996, 118, 10365-10370.
-
(1995)
Trends Biotechnol.
, vol.13
, pp. 63-70
-
-
Carrea, G.1
Ottolina, G.2
Riva, S.3
-
15
-
-
0029818293
-
-
Wescott, C. R.; Klibanov, A. M. Biochim. Biophys. Acta 1994, 1206, 1-9. Carrea, G.; Ottolina, G.; Riva, S. Trends Biotechnol. 1995, 13, 63-70. Wescott, C. R.; Noritomi, H.; Klibanov, A. M. J. Am. Chem. Soc. 1996, 118, 10365-10370.
-
(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 10365-10370
-
-
Wescott, C.R.1
Noritomi, H.2
Klibanov, A.M.3
-
16
-
-
0000983403
-
-
Stahl, M.; Jeppsson-Wistrand, U.; Mansson, M.-O.; Mosbach, K. J. Am. Chem. Soc. 1991, 113, 9366-9368. Noritomi, H.; Almarsson, Ö.; Barletta, G. L.; Klibanov, A. M. Biotechnol Bioeng. 1996, 51, 95-98. Ke, T.; Klibanov, A. M. Biotechnol. Bioeng. 1998, 57, 746-750.
-
(1991)
J. Am. Chem. Soc.
, vol.113
, pp. 9366-9368
-
-
Stahl, M.1
Jeppsson-Wistrand, U.2
Mansson, M.-O.3
Mosbach, K.4
-
17
-
-
0030570503
-
-
Stahl, M.; Jeppsson-Wistrand, U.; Mansson, M.-O.; Mosbach, K. J. Am. Chem. Soc. 1991, 113, 9366-9368. Noritomi, H.; Almarsson, Ö.; Barletta, G. L.; Klibanov, A. M. Biotechnol Bioeng. 1996, 51, 95-98. Ke, T.; Klibanov, A. M. Biotechnol. Bioeng. 1998, 57, 746-750.
-
(1996)
Biotechnol Bioeng.
, vol.51
, pp. 95-98
-
-
Noritomi, H.1
Almarsson, Ö.2
Barletta, G.L.3
Klibanov, A.M.4
-
18
-
-
0032549603
-
-
Stahl, M.; Jeppsson-Wistrand, U.; Mansson, M.-O.; Mosbach, K. J. Am. Chem. Soc. 1991, 113, 9366-9368. Noritomi, H.; Almarsson, Ö.; Barletta, G. L.; Klibanov, A. M. Biotechnol Bioeng. 1996, 51, 95-98. Ke, T.; Klibanov, A. M. Biotechnol. Bioeng. 1998, 57, 746-750.
-
(1998)
Biotechnol. Bioeng.
, vol.57
, pp. 746-750
-
-
Ke, T.1
Klibanov, A.M.2
-
19
-
-
20644469267
-
-
Chen, C.-S.; Fujimoto, Y.; Girdaukas, G.; Sih, C. J. J. Am. Chem. Soc. 1982, 104, 7294-7299. Straathof, A. J. J.; Jongejan, J. A. Enzyme Microb. Technol. 1997, 21, 559-571.
-
(1982)
J. Am. Chem. Soc.
, vol.104
, pp. 7294-7299
-
-
Chen, C.-S.1
Fujimoto, Y.2
Girdaukas, G.3
Sih, C.J.4
-
20
-
-
0031455616
-
-
Chen, C.-S.; Fujimoto, Y.; Girdaukas, G.; Sih, C. J. J. Am. Chem. Soc. 1982, 104, 7294-7299. Straathof, A. J. J.; Jongejan, J. A. Enzyme Microb. Technol. 1997, 21, 559-571.
-
(1997)
Enzyme Microb. Technol.
, vol.21
, pp. 559-571
-
-
Straathof, A.J.J.1
Jongejan, J.A.2
-
22
-
-
0027321564
-
-
Fitzpatrick, P. A.; Steinmetz, A. C. U.; Ringe, D.; Klibanov, A. M. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 8653-8657. Fitzpatrick, P. A.; Ringe, D.; Klibanov, A. M. Biochem. Biophys. Res. Commun. 1994, 198, 675-681. Schmitke, J. L.; Stern, L. J.; Klibanov, A. M. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 4250-4255. Schmitke, J. L.; Stern, L. J.; Klibanov, A. M. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 12918-12923.
-
(1993)
Proc. Natl. Acad. Sci. U.S.A.
, vol.90
, pp. 8653-8657
-
-
Fitzpatrick, P.A.1
Steinmetz, A.C.U.2
Ringe, D.3
Klibanov, A.M.4
-
23
-
-
0028304966
-
-
Fitzpatrick, P. A.; Steinmetz, A. C. U.; Ringe, D.; Klibanov, A. M. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 8653-8657. Fitzpatrick, P. A.; Ringe, D.; Klibanov, A. M. Biochem. Biophys. Res. Commun. 1994, 198, 675-681. Schmitke, J. L.; Stern, L. J.; Klibanov, A. M. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 4250-4255. Schmitke, J. L.; Stern, L. J.; Klibanov, A. M. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 12918-12923.
-
(1994)
Biochem. Biophys. Res. Commun.
, vol.198
, pp. 675-681
-
-
Fitzpatrick, P.A.1
Ringe, D.2
Klibanov, A.M.3
-
24
-
-
0030970824
-
-
Fitzpatrick, P. A.; Steinmetz, A. C. U.; Ringe, D.; Klibanov, A. M. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 8653-8657. Fitzpatrick, P. A.; Ringe, D.; Klibanov, A. M. Biochem. Biophys. Res. Commun. 1994, 198, 675-681. Schmitke, J. L.; Stern, L. J.; Klibanov, A. M. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 4250-4255. Schmitke, J. L.; Stern, L. J.; Klibanov, A. M. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 12918-12923.
-
(1997)
Proc. Natl. Acad. Sci. U.S.A.
, vol.94
, pp. 4250-4255
-
-
Schmitke, J.L.1
Stern, L.J.2
Klibanov, A.M.3
-
25
-
-
0032573075
-
-
Fitzpatrick, P. A.; Steinmetz, A. C. U.; Ringe, D.; Klibanov, A. M. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 8653-8657. Fitzpatrick, P. A.; Ringe, D.; Klibanov, A. M. Biochem. Biophys. Res. Commun. 1994, 198, 675-681. Schmitke, J. L.; Stern, L. J.; Klibanov, A. M. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 4250-4255. Schmitke, J. L.; Stern, L. J.; Klibanov, A. M. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 12918-12923.
-
(1998)
Proc. Natl. Acad. Sci. U.S.A.
, vol.95
, pp. 12918-12923
-
-
Schmitke, J.L.1
Stern, L.J.2
Klibanov, A.M.3
-
27
-
-
2442762093
-
-
note
-
15 The other three cross-linked crystalline enzymes, commercially available from Altus Biologics, Inc., were generously donated by that company.
-
-
-
-
28
-
-
0029959897
-
-
Ke, T.; Wescott, C. R.; Klibanov, A. M. J. Am. Chem. Soc. 1996, 118, 3366-3374. Ke, T.; Klibanov, A. M. J. Am. Chem. Soc. 1998, 120, 4259-4263.
-
(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 3366-3374
-
-
Ke, T.1
Wescott, C.R.2
Klibanov, A.M.3
-
29
-
-
0032513720
-
-
Ke, T.; Wescott, C. R.; Klibanov, A. M. J. Am. Chem. Soc. 1996, 118, 3366-3374. Ke, T.; Klibanov, A. M. J. Am. Chem. Soc. 1998, 120, 4259-4263.
-
(1998)
J. Am. Chem. Soc.
, vol.120
, pp. 4259-4263
-
-
Ke, T.1
Klibanov, A.M.2
-
30
-
-
2442744941
-
-
note
-
The structure of all Brønsted-Lowry salts examined in this work was confirmed by FTIR spectroscopy, as described in the Methods section.
-
-
-
-
31
-
-
0010237021
-
-
Schrag, J. D.; Li, Y.; Cygler, M.; Lang, D.; Burgdorf, T.; Hecht, H.-J.; Schmid, R.; Schomburg, D.; Rydel, T. J.; Oliver, J. D.; Strickland, L. C.; Dunaway, C. M.; Larson, S. B.; Day, J.; McPherson, A. Structure 1997, 5, 187-202.
-
(1997)
Structure
, vol.5
, pp. 187-202
-
-
Schrag, J.D.1
Li, Y.2
Cygler, M.3
Lang, D.4
Burgdorf, T.5
Hecht, H.-J.6
Schmid, R.7
Schomburg, D.8
Rydel, T.J.9
Oliver, J.D.10
Strickland, L.C.11
Dunaway, C.M.12
Larson, S.B.13
Day, J.14
McPherson, A.15
-
32
-
-
0003596148
-
-
Pharmaceutical Press: London
-
These include atropine, hyoscyamine, and scopolamine (Reynolds, J. E. F., Ed. Martindale, the Extra Pharmacopoeia, 28th ed.; Pharmaceutical Press: London, 1982; p 304).
-
(1982)
Martindale, the Extra Pharmacopoeia, 28th Ed.
, pp. 304
-
-
Reynolds, J.E.F.1
-
33
-
-
2442735053
-
-
note
-
Subtilisin and C. rugosa lipase were found to be catalytically inactive in this reaction, while chymotrypsin was both active and very enantio-selective (E = 12.2 ± 0.2).
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-
-
-
34
-
-
2442763565
-
-
note
-
In 30 mL of anhydrous acetonitrile, 1.2 mmol of R,S-3 (or its quinuclidine salt) and 6 mmol of vinyl acetate were dissolved. The enzymatic acetylation was initiated by adding 60 mg of CLC P. cepacia lipase. The reaction mixture was shaken at 300 rpm and 30°C for 8.3 h (free substrate) or 12.1 h (substrate salt). Then the enzyme was removed by filtration, and the remaining solution was worked up by rotary evaporation, redissolution in 60% ethyl acetate/40% hexane/0.1% trifluoroacetic acid (which decomposes the salt), and using this solvent as a mobile phase in flash silica gel column chromatography (see Methods for details).
-
-
-
-
37
-
-
2442747778
-
-
Wolffenstein, M. Chem. Ber. 1908, 41, 730-736. Schmidt, R. J. Pharm. Sci. 1968, 57, 443-452.
-
(1908)
Chem. Ber.
, vol.41
, pp. 730-736
-
-
Wolffenstein, M.1
-
38
-
-
0014264253
-
-
Wolffenstein, M. Chem. Ber. 1908, 41, 730-736. Schmidt, R. J. Pharm. Sci. 1968, 57, 443-452.
-
(1968)
J. Pharm. Sci.
, vol.57
, pp. 443-452
-
-
Schmidt, R.1
-
39
-
-
0003481596
-
-
Freeman: New York
-
Fersht, A. Enzyme Structure and Mechanism, 2nd ed.; Freeman: New York, 1985; p 112. Wescott, C. R.; Klibanov, A. M. J. Am. Chem. Soc. 1993, 115, 1629-1631.
-
(1985)
Enzyme Structure and Mechanism, 2nd Ed.
, pp. 112
-
-
Fersht, A.1
-
40
-
-
0000764219
-
-
Fersht, A. Enzyme Structure and Mechanism, 2nd ed.; Freeman: New York, 1985; p 112. Wescott, C. R.; Klibanov, A. M. J. Am. Chem. Soc. 1993, 115, 1629-1631.
-
(1993)
J. Am. Chem. Soc.
, vol.115
, pp. 1629-1631
-
-
Wescott, C.R.1
Klibanov, A.M.2
-
46
-
-
0024538543
-
-
Warshel, A.; Naray-Szabo, G.; Sussman, F.; Hwang, J.-K. Biochemistry 1989, 28, 3629-3635.
-
(1989)
Biochemistry
, vol.28
, pp. 3629-3635
-
-
Warshel, A.1
Naray-Szabo, G.2
Sussman, F.3
Hwang, J.-K.4
-
47
-
-
2842567678
-
-
Donohue, J. J. Phys. Chem. 1952, 56, 502-510. Fuller, W. J. Phys. Chem. 1959, 63, 1705-1717.
-
(1952)
J. Phys. Chem.
, vol.56
, pp. 502-510
-
-
Donohue, J.1
-
48
-
-
0000000861
-
-
Donohue, J. J. Phys. Chem. 1952, 56, 502-510. Fuller, W. J. Phys. Chem. 1959, 63, 1705-1717.
-
(1959)
J. Phys. Chem.
, vol.63
, pp. 1705-1717
-
-
Fuller, W.1
-
50
-
-
0026928586
-
-
Fitzpatrick, P. A.; Ringe, D.; Klibanov, A. M. Biotechnol. Bioeng. 1992, 40, 735-740.
-
(1992)
Biotechnol. Bioeng.
, vol.40
, pp. 735-740
-
-
Fitzpatrick, P.A.1
Ringe, D.2
Klibanov, A.M.3
|