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For systematic studies of solvent effects on enzymatic transesterification reactions, see: (a)
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For systematic studies of solvent effects on enzymatic transesterification reactions, see: (a) Kitano, K.; Matsubara, J.; Ohtani, T.; Otsubo, K.; Kawano, Y.; Morita, S.; Uchida, M. Tetrahedron Lett. 1999, 40, 5235-5238;
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(c) Ducret, A.; Trani, M.; Lortie, R. Enzyme Microb. Technol. 1998, 22, 212-216;
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(d) Wescott, C. R.; Noritomi, H.; Klibanov, A. M. J. Am. Chem. Soc. 1996, 118, 10365-10370;
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(e) Chaudhary, A. K.; Kamat, S. V.; Beckman, E. J.; Nurok, D.; Kleyle, R. M.; Hajdu, P.; Russell, A. J. J. Am. Chem. Soc. 1996, 118, 12891-12901;
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(f) Morrone, R.; Nicolosi, G.; Patti, A.; Piatelli, M. Tetrahedron: Asymmetry 1995, 6, 1773-1778;
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(h) Triantafyllou, A. Ö.; Aldercreutz, P.; Mattiasson, B. Biotechnol. Appl. Biochem. 1993, 17, 167-179;
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(l) Antczak, U.; Góra, J.; Antczak, T.; Galas, E. Enzyme Microb. Technol. 1991, 13, 589-593.
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Antczak, U.1
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0029120269
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For example, see: (EtOH, microsomal epoxide hydrolase).
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For example, see: Belluci, G.; Chiappe, C.; Ingrosso, G.; Rosini, C. Tetrahedron: Asymmetry 1995, 6, 1911-1918 (EtOH, microsomal epoxide hydrolase).
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Belluci, G.1
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23
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0033597912
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For recent examples of systems where enzymatic ester hydrolysis is superior to esterification, particularly in terms of % ee, see: (a) (no cosolvent, 14 days)
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For recent examples of systems where enzymatic ester hydrolysis is superior to esterification, particularly in terms of % ee, see: (a) Luzzio, F. A.; Fitch, R. W. J. Org. Chem. 1999, 64, 5485-5493 (no cosolvent, 14 days);
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Luzzio, F.A.1
Fitch, R.W.2
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(b) (CAL, MeOH)
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(b) Adam, W.; Diaz, M. T.; Saha-Moller, C. R. Tetrahedron: Asymmetry 1998, 9, 589-598 (CAL, MeOH);
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Adam, W.1
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25
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0030831509
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(c) (lipase AK, THF)
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(c) Morgan, B.; Dodds, D. R.; Zaks, A.; Andrews, D. R.; Klesse, R. J. Org. Chem. 1997, 62, 7736-7743 (lipase AK, THF);
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Morgan, B.1
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Klesse, R.5
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(d) (PPL, DMSO).
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(d) Berkowitz, D. B.; Maeng, J.-H. Tetrahedron: Asymmetry 1996, 7, 1577-1580 (PPL, DMSO).
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Berkowitz, D.B.1
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0030272259
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(a) (biphasic hydrolysis, 1-3 days);
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(a) Lampe, T. F. J.; Hoffmann, H. M. R.; Bornscheuer, U. T. Tetrahedron: Asymmetry 1996, 7, 2889-2900 (biphasic hydrolysis, 1-3 days);
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Lampe, T.F.J.1
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0029798502
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(b) (biphasic hydrolysis, 4-7 days).
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(b) Desai, S. B.; Argade, N. P.; Ganesh, K. N. J. Org. Chem. 1996, 61, 6730-6732 (biphasic hydrolysis, 4-7 days).
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Desai, S.B.1
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0030999709
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For solvent effects upon enzymatic hydrolyses carried out in water-saturated organic solvents, see: (a)
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For solvent effects upon enzymatic hydrolyses carried out in water-saturated organic solvents, see: (a) Akita, H.; Umezawa, I.; Matsukura, H. Chem. Pharm. Bull. 1997, 45, 272-278;
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(b) Hirose, Y.; Kariya, K.; Sasaki, I.; Kurono, Y.; Ebiike, H.; Achiwa, K. Tetrahedron Lett. 1992, 33, 7157-7160;
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(c) Tramper, J.; Vermue, M. H.; Beeftink, H. H., Eds.; Elsevier: Amsterdam
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(c) Ausseil, F.; Biaudet, H.; Masson, P. In Biocatalysis in Non-Conventional Media; Tramper, J.; Vermue, M. H.; Beeftink, H. H., Eds.; Elsevier: Amsterdam, 1992; pp. 593-600;
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For general studies of chymotrypsin- and trypsin-catalyzed hydrolyses in homogeneous organic-aqueous media, see: (a)
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For general studies of chymotrypsin- and trypsin-catalyzed hydrolyses in homogeneous organic-aqueous media, see: (a) Vidal, M. I.; Serralheiro, M. L. M.; Cabral, J. M. S. Biotechnol. Lett. 1992, 14, 1041-1044;
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(b) Guinn, R. M.; Blanch, H. W.; Clark, D. S. Enzyme Microb. Technol. 1991, 13, 320-326;
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Blanch, H.W.2
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(c) Khmelnitsky, Y. L.; Mozhaev, V. V.; Belova, A. B.; Sergeeva, M. V.; Martinek, K. Eur. J. Biochem. 1991, 198, 31-41;
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Khmelnitsky, Y.L.1
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Martinek, K.5
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0024747511
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(d) Mozhaev, V. V.; Khmelnitsky, Y. L.; Sergeeva, M. V.; Belova, A. B.; Klyachko, N. L. Eur. J. Biochem. 1989, 184, 597-602;
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Klyachko, N.L.5
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38
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0032554713
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For selected examples of the use of organic cosolvents in the hydrolytic enzymatic resolution/desymmetrization of synthetic intermediates, see: (a) (MeOH; CAL)
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For selected examples of the use of organic cosolvents in the hydrolytic enzymatic resolution/desymmetrization of synthetic intermediates, see: (a) Adamczyk, M.; Grote, J.; Rege, S. Bioorg. Med. Chem. Lett. 1998, 8, 885-890 (MeOH; CAL);
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Adamczyk, M.1
Grote, J.2
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0032570501
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(b) (MeCN, acetone, THF; PLE and Mucor miehei lipase)
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(b) Ranchoux, M.; Brunel, J.-M.; Iacazio, G.; Buono, G. Tetrahedron: Asymmetry 1998, 9, 581-587 (MeCN, acetone, THF; PLE and Mucor miehei lipase);
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Ranchoux, M.1
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Iacazio, G.3
Buono, G.4
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(c) Kang, S.-K.; Jeon, J.-H.; Yamaguchi, T.; Hong, R.-K.; Ko, B.-S. Tetrahedron: Asymmetry 1995, 6, 97-100 (acetone; PPL);
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Kang, S.-K.1
Jeon, J.-H.2
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Ko, B.-S.5
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0026440285
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(d) (THF, t-BuOH; CAL)
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(d) Johnson, C. R.; Bis, S. J. Tetrahedron Lett. 1992, 33, 7287-7290 (THF, t-BuOH; CAL);
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Johnson, C.R.1
Bis, S.J.2
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(f) (DMSO, t-BuOH, DMEU; PLE).
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(f) Guranti, G.; Banfi, L.; Narisano, E.; Riva, R.; Thea, S. Tetrahedron Lett. 1986, 27, 4639-4642 (DMSO, t-BuOH, DMEU; PLE).
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Guranti, G.1
Banfi, L.2
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44
-
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0027982335
-
-
For a tabulation of various log P values and a discussion of methods for calculating/measuring these, see: and references cited therein.
-
For a tabulation of various log P values and a discussion of methods for calculating/measuring these, see: Abraham, M. H.; Chadha, H. S.; Whiting, G. S.; Mitchell, R. C. J. Pharm. Sci. 1994, 83, 1085-1100 and references cited therein.
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85038059805
-
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Note: In at least one case involving subtilisin Carlsberg-mediated transesterifications with n-BuOH, increasing % ee correlates better with (decreasing) dipole moment than with (increasing) log P, see Ref. 5j.
-
Note: In at least one case involving subtilisin Carlsberg-mediated transesterifications with n-BuOH, increasing % ee correlates better with (decreasing) dipole moment than with (increasing) log P, see Ref. 5j.
-
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48
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84982010057
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(a) Yosphe-Besonçon, I.; Auriol, D.; Paul, F.; Monsan, P.; Gripon, J.-C.; Ribadeau-Dumas, B. Biotechnol. Appl. Biochem. 1993, 18, 93-102;
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