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Volumn 10, Issue 23, 1999, Pages 4513-4520

Hydrolytic enzymatic transformation of advanced synthetic intermediates: On the choice of the organic cosolvent

Author keywords

[No Author keywords available]

Indexed keywords

ACETONE; ACETONITRILE; DIGLYME; DIMETHYL SULFOXIDE; DIOXANE; ORGANIC SOLVENT; PODOPHYLLOTOXIN; POLYETHER DERIVATIVE; PYRIDINE; TRIGLYME; UNCLASSIFIED DRUG;

EID: 0033399646     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00509-1     Document Type: Article
Times cited : (14)

References (49)
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    • (b)
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    • (e)
    • (e) Wong, C.-H. Science 1989, 244, 1145-1152.
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    • For a study of lyophilized protein structure as a function of organic solvent, see:
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    • Desai, U.R.1    Klibanov, A.M.2
  • 8
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    • For general discussions on the effect of organic solvents upon enzymatic reactions, see: (a)
    • For general discussions on the effect of organic solvents upon enzymatic reactions, see: (a) Kvittingen, L. Tetrahedron 1994, 50, 8253-8274;
    • (1994) Tetrahedron , vol.50 , pp. 8253-8274
    • Kvittingen, L.1
  • 10
    • 0033538604 scopus 로고    scopus 로고
    • For systematic studies of solvent effects on enzymatic transesterification reactions, see: (a)
    • 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;
    • (1999) Tetrahedron Lett. , vol.40 , pp. 5235-5238
    • Kitano, K.1    Matsubara, J.2    Ohtani, T.3    Otsubo, K.4    Kawano, Y.5    Morita, S.6    Uchida, M.7
  • 23
    • 0033597912 scopus 로고    scopus 로고
    • For recent examples of systems where enzymatic ester hydrolysis is superior to esterification, particularly in terms of % ee, see: (a) (no cosolvent, 14 days)
    • 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);
    • (1999) J. Org. Chem. , vol.64 , pp. 5485-5493
    • Luzzio, F.A.1    Fitch, R.W.2
  • 28
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    • (b) (biphasic hydrolysis, 4-7 days).
    • (b) Desai, S. B.; Argade, N. P.; Ganesh, K. N. J. Org. Chem. 1996, 61, 6730-6732 (biphasic hydrolysis, 4-7 days).
    • (1996) J. Org. Chem. , vol.61 , pp. 6730-6732
    • Desai, S.B.1    Argade, N.P.2    Ganesh, K.N.3
  • 29
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    • For solvent effects upon enzymatic hydrolyses carried out in water-saturated organic solvents, see: (a)
    • 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;
    • (1997) Chem. Pharm. Bull. , vol.45 , pp. 272-278
    • Akita, H.1    Umezawa, I.2    Matsukura, H.3
  • 33
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    • For general studies of chymotrypsin- and trypsin-catalyzed hydrolyses in homogeneous organic-aqueous media, see: (a)
    • 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;
    • (1992) Biotechnol. Lett. , vol.14 , pp. 1041-1044
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  • 38
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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)
    • 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);
    • (1998) Bioorg. Med. Chem. Lett. , vol.8 , pp. 885-890
    • Adamczyk, M.1    Grote, J.2    Rege, S.3
  • 44
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    • 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.
    • (1994) J. Pharm. Sci. , vol.83 , pp. 1085-1100
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  • 45
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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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    • (b) Fr. Demande FR 2,609,376, 15 July
    • (b) Paul, F. B.; Monsan, P. F.; Auriol, D. H. Fr. Demande FR 2,609,376, 15 July 1988.
    • (1988)
    • Paul, F.B.1    Monsan, P.F.2    Auriol, D.H.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.