-
7
-
-
0029872834
-
-
Schoffers, E.; Golebiowski, A.; Johnson, C. R. Tetrahedron 1996, 52, 3769-3826.
-
(1996)
Tetrahedron
, vol.52
, pp. 3769-3826
-
-
Schoffers, E.1
Golebiowski, A.2
Johnson, C.R.3
-
8
-
-
0029163690
-
-
Wong, C.-H.; Halcomb, R. L.; Ichikawa, Y.; Kajimoto, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 521-546.
-
(1995)
Angew. Chem., Int. Ed. Engl.
, vol.34
, pp. 521-546
-
-
Wong, C.-H.1
Halcomb, R.L.2
Ichikawa, Y.3
Kajimoto, T.4
-
9
-
-
0029109703
-
-
Wong, C.-H.; Halcomb, R. L.; Ichikawa, Y.; Kajimoto, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 412-432.
-
(1995)
Angew. Chem., Int. Ed. Engl.
, vol.34
, pp. 412-432
-
-
Wong, C.-H.1
Halcomb, R.L.2
Ichikawa, Y.3
Kajimoto, T.4
-
11
-
-
2642642035
-
-
Gijsen, H. J. M.; Qiao, L.; Fitz, W.; Wong, C.-H. Chem. Rev. 1996, 96, 443-473.
-
(1996)
Chem. Rev.
, vol.96
, pp. 443-473
-
-
Gijsen, H.J.M.1
Qiao, L.2
Fitz, W.3
Wong, C.-H.4
-
12
-
-
0001907528
-
-
Scheffold, R., Ed.; Springer-Verlag: Berlin
-
Crout, D. H. G.; Christen, M. in Biotransformations in Organic Synthesis; Scheffold, R., Ed.; Springer-Verlag: Berlin, 1989; pp 1-114.
-
(1989)
Biotransformations in Organic Synthesis
, pp. 1-114
-
-
Crout, D.H.G.1
Christen, M.2
-
13
-
-
4243794106
-
-
Santaniello, E.; Ferraboschi, P.; Grisenti, P.; Manzocchi, A. Chem. Rev. 1992, 92, 1071-1140.
-
(1992)
Chem. Rev.
, vol.92
, pp. 1071-1140
-
-
Santaniello, E.1
Ferraboschi, P.2
Grisenti, P.3
Manzocchi, A.4
-
14
-
-
0003755345
-
-
Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Academic Press: New York
-
Davies, H. G.; Green, R. H.; Kelly, D. R.; Roberts, S. M. Biotransformations in Preparative Organic Chemistry. The Use of Isolated Enzymes and Whole Cell Systems in Synthesis; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Academic Press: New York, 1989.
-
(1989)
Biotransformations in Preparative Organic Chemistry. The Use of Isolated Enzymes and Whole Cell Systems in Synthesis
-
-
Davies, H.G.1
Green, R.H.2
Kelly, D.R.3
Roberts, S.M.4
-
16
-
-
0000081799
-
-
(a) Stewart, J. D.; Reed, K. W.; Kayser, M. M. J. Chem. Soc., Perkin Trans. 1 1996, 755-757.
-
(1996)
J. Chem. Soc., Perkin Trans. 1
, pp. 755-757
-
-
Stewart, J.D.1
Reed, K.W.2
Kayser, M.M.3
-
17
-
-
0000779198
-
-
(b) Stewart, J. D.; Reed, K. W.; Zhu, J.; Chen, G.; Kayser, M. M. J. Org. Chem. 1996, 61, 7652-7653.
-
(1996)
J. Org. Chem.
, vol.61
, pp. 7652-7653
-
-
Stewart, J.D.1
Reed, K.W.2
Zhu, J.3
Chen, G.4
Kayser, M.M.5
-
18
-
-
0017227971
-
-
Donoghue, N. A.; Norris, D. B.; Trudgill, P. W. Eur. J. Biochem. 1976, 63, 175-192.
-
(1976)
Eur. J. Biochem.
, vol.63
, pp. 175-192
-
-
Donoghue, N.A.1
Norris, D.B.2
Trudgill, P.W.3
-
19
-
-
7144244562
-
-
in press
-
For a review of Baeyer-Villiger reactions catalyzed by cyclohexanone monooxygenase, see Stewart, J. D. Curr. Org. Chem. 1998, in press.
-
(1998)
Curr. Org. Chem.
-
-
Stewart, J.D.1
-
21
-
-
0029877714
-
-
Seelbach, K.; Riebel, B.; Hummel, W.; Kula, M.-R.; Tishkov, V.; Egorov, A. M.; Wandrey, C.; Kragl, U. Tetrahedron Lett. 1996, 1377-1380.
-
(1996)
Tetrahedron Lett.
, pp. 1377-1380
-
-
Seelbach, K.1
Riebel, B.2
Hummel, W.3
Kula, M.-R.4
Tishkov, V.5
Egorov, A.M.6
Wandrey, C.7
Kragl, U.8
-
22
-
-
0023958999
-
-
Chen, Y.-C. J.; Peoples, O. P.; Walsh, C. T. J. Bacteriol. 1988, 170, 781-789.
-
(1988)
J. Bacteriol.
, vol.170
, pp. 781-789
-
-
Chen, Y.-C.J.1
Peoples, O.P.2
Walsh, C.T.3
-
23
-
-
7144246339
-
-
note
-
Plasmids used: M949 (David Stillman, University of Utah), ARS-CEN origin of replication, GAL promoter; pYES2 (Invitrogen, Inc.), 2 micron circle origin of replication, GAL promoter; pG-3 (Kieth Yamamoto, University of California, San Francisco), 2 micron circle origin of replication, GPD promoter.
-
-
-
-
24
-
-
7144230606
-
-
S. cerevisiae 15C: MATα, leu2, ura3-52, Δtrp1, his4-80, pep4-3
-
S. cerevisiae 15C: MATα, leu2, ura3-52, Δtrp1, his4-80, pep4-3.
-
-
-
-
28
-
-
33845379674
-
-
Shieh, W.-R.; Gopalin, A. S.; Sih, C. J. J. Am. Chem. Soc. 1985, 107, 7, 2993-2994.
-
(1985)
J. Am. Chem. Soc.
, vol.107
, Issue.7
, pp. 2993-2994
-
-
Shieh, W.-R.1
Gopalin, A.S.2
Sih, C.J.3
-
29
-
-
0000414031
-
-
Nakamura, K.; Kawai, Y.; Nakajima, N.; Ohno, A. J. Org. Chem. 1991, 56, 4778-4783.
-
(1991)
J. Org. Chem.
, vol.56
, pp. 4778-4783
-
-
Nakamura, K.1
Kawai, Y.2
Nakajima, N.3
Ohno, A.4
-
30
-
-
0028253983
-
-
Nakamura, K.; Kondo, S.; Kawai, Y.; Nakajima, N.; Ohno, A. Biosci. Biotech. Biochem. 1994, 58, 2236-2240.
-
(1994)
Biosci. Biotech. Biochem.
, vol.58
, pp. 2236-2240
-
-
Nakamura, K.1
Kondo, S.2
Kawai, Y.3
Nakajima, N.4
Ohno, A.5
-
33
-
-
0029588274
-
-
Anderson, B. A.; Hansen, M. M.; Harkness, A. R.; Henry, C. L.; Vicenzi, J. T.; Zmijewski, M. J. J. Am. Chem. Soc. 1995, 117, 12358-12359.
-
(1995)
J. Am. Chem. Soc.
, vol.117
, pp. 12358-12359
-
-
Anderson, B.A.1
Hansen, M.M.2
Harkness, A.R.3
Henry, C.L.4
Vicenzi, J.T.5
Zmijewski, M.J.6
-
37
-
-
0025773494
-
-
Singer, Y.; Shity, H.; Bar, R. Appl. Microbiol. Biotechnol. 1991, 35, 731-737.
-
(1991)
Appl. Microbiol. Biotechnol.
, vol.35
, pp. 731-737
-
-
Singer, Y.1
Shity, H.2
Bar, R.3
-
38
-
-
7144229567
-
-
Details of this synthesis will be published elsewhere
-
Details of this synthesis will be published elsewhere.
-
-
-
-
39
-
-
0027276331
-
-
Taschner, M. J.; Black, D. J.; Chen, Q.-Z. Tetrahedron: Asymmetry 1993, 4, 1387-1390.
-
(1993)
Tetrahedron: Asymmetry
, vol.4
, pp. 1387-1390
-
-
Taschner, M.J.1
Black, D.J.2
Chen, Q.-Z.3
-
40
-
-
0000278041
-
-
Meinwald, J.; Tufariello, J. J.; Hurst, J. J. J. Org. Chem. 1964, 29, 9, 2914-2919.
-
(1964)
J. Org. Chem.
, vol.29
, Issue.9
, pp. 2914-2919
-
-
Meinwald, J.1
Tufariello, J.J.2
Hurst, J.J.3
-
41
-
-
84990161999
-
-
Walsh, C. T.; Chen, Y.-C. J. Angew. Chem., Int. Ed. Engl. 1988, 27, 333-343.
-
(1988)
Angew. Chem., Int. Ed. Engl.
, vol.27
, pp. 333-343
-
-
Walsh, C.T.1
Chen, Y.-C.J.2
-
44
-
-
33749085185
-
-
During the course of our work, Alphand et al. published their independent studies of the Baeyer-Villiger oxidations of 2-alkyl-substituted cyclohexanones by whole Acinetobacter cells: Alphand, V.; Furstoss, R.; Pedragosa-Moreau, S.; Roberts, S. M.; Willetts, A. J. J. Chem. Soc., Perkin Trans 1 1996, 1867-1872. Our results are in good agreement.
-
(1996)
J. Chem. Soc., Perkin Trans 1
, pp. 1867-1872
-
-
Alphand, V.1
Furstoss, R.2
Pedragosa-Moreau, S.3
Roberts, S.M.4
Willetts, A.J.5
-
45
-
-
0020783603
-
-
Schwab, J. M.; Li, W.-b.; Thomas, L. P. J. Am. Chem. Soc. 1983, 105, 5, 4800-4808.
-
(1983)
J. Am. Chem. Soc.
, vol.105
, Issue.5
, pp. 4800-4808
-
-
Schwab, J.M.1
Li, W.-B.2
Thomas, L.P.3
-
47
-
-
33947482604
-
-
Stork, G.; Brizzolara, A.; Landesman, H.; Szmuszkovicz, J.; Terrell, R. J. Am. Chem. Soc. 1963, 85, 207-222.
-
(1963)
J. Am. Chem. Soc.
, vol.85
, pp. 207-222
-
-
Stork, G.1
Brizzolara, A.2
Landesman, H.3
Szmuszkovicz, J.4
Terrell, R.5
-
48
-
-
20644469267
-
-
(a) Chen, C.-S.; Fujimoto, Y.; Girdaukas, G.; Sih, C. J. J. Am. Chem. Soc. 1982, 104, 7294-7299.
-
(1982)
J. Am. Chem. Soc.
, vol.104
, pp. 7294-7299
-
-
Chen, C.-S.1
Fujimoto, Y.2
Girdaukas, G.3
Sih, C.J.4
-
49
-
-
7144237106
-
-
note
-
1/(1 - E) where c = fractional conversion, ee(S) = enantiomeric excess of the remaining substrate, and E = enantioselectivity value.
-
-
-
-
50
-
-
7144231675
-
-
note
-
Note that there is a change in numbering priority for ketones 7d and 7f which inverts the (R/S) nomenclature.
-
-
-
-
52
-
-
0001738365
-
-
Saigo, K.; Kasahara, A.; Ogawa, S.; Nohira, H. Tetrahedron Lett. 1983, 511-512.
-
(1983)
Tetrahedron Lett.
, pp. 511-512
-
-
Saigo, K.1
Kasahara, A.2
Ogawa, S.3
Nohira, H.4
-
54
-
-
0024316993
-
-
Kim, H.-d.; Kawasaki, H.; Nakajima, M.; Koga, K. Tetrahedron Lett. 1989, 6537-6540.
-
(1989)
Tetrahedron Lett.
, pp. 6537-6540
-
-
Kim, H.-D.1
Kawasaki, H.2
Nakajima, M.3
Koga, K.4
-
55
-
-
0028327518
-
-
Fellous, R.; Lizzani-Cuvelier, L.; Loiseau, M. A.; Sassy, E. Tetrahedron: Asymmetry 1994, 5, 343-346.
-
(1994)
Tetrahedron: Asymmetry
, vol.5
, pp. 343-346
-
-
Fellous, R.1
Lizzani-Cuvelier, L.2
Loiseau, M.A.3
Sassy, E.4
-
56
-
-
0000281042
-
-
(a) Taschner, M. J.; Peddada, L.; Cyr, P.; Chen, Q. Z.; Black, D. J. NATO ASI Ser., Ser. C 1992, 381, 347-360.
-
(1992)
NATO ASI Ser., Ser. C
, vol.381
, pp. 347-360
-
-
Taschner, M.J.1
Peddada, L.2
Cyr, P.3
Chen, Q.Z.4
Black, D.J.5
-
62
-
-
0003407893
-
-
Eisenbraun, E. J.; McElvain, S. M. J. Am. Chem. Soc. 1955, 77, 7, 3383-3384.
-
(1955)
J. Am. Chem. Soc.
, vol.77
, Issue.7
, pp. 3383-3384
-
-
Eisenbraun, E.J.1
McElvain, S.M.2
-
63
-
-
7144225763
-
-
Both enantiomers of pulegone are commercially available from Fluka Chemical Corp.
-
Both enantiomers of pulegone are commercially available from Fluka Chemical Corp.
-
-
-
-
69
-
-
0029075087
-
-
Ottolina, G.; Pasta, P.; Carrea, G.; Colonna, S.; Dallavalle, S.; Holland, H. L. Tetrahedron: Asymmetry 1995, 6, 1375-1386.
-
(1995)
Tetrahedron: Asymmetry
, vol.6
, pp. 1375-1386
-
-
Ottolina, G.1
Pasta, P.2
Carrea, G.3
Colonna, S.4
Dallavalle, S.5
Holland, H.L.6
-
70
-
-
0029989509
-
-
Ottolina, G.; Carrea, G.; Colonna, S.; Rückemann, A. Tetrahedron: Asymmetry 1996, 7, 1123-1136.
-
(1996)
Tetrahedron: Asymmetry
, vol.7
, pp. 1123-1136
-
-
Ottolina, G.1
Carrea, G.2
Colonna, S.3
Rückemann, A.4
-
71
-
-
7144233531
-
-
note
-
- or OH.
-
-
-
-
72
-
-
0000717321
-
-
Krow, G. R. Tetrahedron 1981, 37, 2697-2724.
-
(1981)
Tetrahedron
, vol.37
, pp. 2697-2724
-
-
Krow, G.R.1
-
74
-
-
7144239811
-
-
note
-
The shape of the enzyme binding pocket in this diagram is only a schematic and does not accurately reproduce the cubic space model of ref 67.
-
-
-
-
75
-
-
7144231673
-
-
note
-
Details of this derivation are given in the Supporting Information for this article.
-
-
-
-
76
-
-
7144234615
-
-
-[ΔGs,eq,ax/(RT)]
-
-[ΔGs,eq,ax/(RT)].
-
-
-
-
77
-
-
0000564056
-
-
Allinger, N. L.; Blatter, H. M.; Freiberg, L. A.; Karkowski, F. M. J. Am. Chem. Soc. 1966, 88, 2999-3011.
-
(1966)
J. Am. Chem. Soc.
, vol.88
, pp. 2999-3011
-
-
Allinger, N.L.1
Blatter, H.M.2
Freiberg, L.A.3
Karkowski, F.M.4
-
84
-
-
0002714675
-
-
Still, W. C.; Kahn, M.; Mitra., A. J. Org. Chem. 1978, 14, 2923-2925.
-
(1978)
J. Org. Chem.
, vol.14
, pp. 2923-2925
-
-
Still, W.C.1
Kahn, M.2
Mitra, A.3
-
87
-
-
0026030413
-
-
Schena, M.; Picard, D.; Yamamoto, K. R. Methods Enzymol. 1991, 194, 389-399.
-
(1991)
Methods Enzymol.
, vol.194
, pp. 389-399
-
-
Schena, M.1
Picard, D.2
Yamamoto, K.R.3
-
89
-
-
7144248428
-
-
note
-
Although the high-resolution mass spectra were obtained under electron-impact conditions, only the M + H ions were observed.
-
-
-
|