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Volumn 14, Issue 3, 1996, Pages 167-179

Preparation of (S)-cyanohydrins by enantioselective cleavage of racemic cyanohydrins with (R)-hydroxynitrile lyase

Author keywords

(R) hydroxynitrile lyase; (S) cyanohydrin synthesis; Enzyme catalyzed resolution

Indexed keywords

ALDEHYDES; AROMATIC COMPOUNDS; CATALYSIS; COMPOSITION EFFECTS; ENZYMES; GLYCOLS; SULFUR COMPOUNDS; SYNTHESIS (CHEMICAL);

EID: 0030683408     PISSN: 10242422     EISSN: None     Source Type: Journal    
DOI: 10.3109/10242429709106884     Document Type: Article
Times cited : (16)

References (36)
  • 1
    • 0030020862 scopus 로고    scopus 로고
    • A Convenient Synthesis of (S)-2-Azidonitriles, (S)-2-Aminonitriles and (S)-1,2-Diamines
    • Enzyme-catalyzed Reactions, Part 25. - Part 24
    • Enzyme-catalyzed Reactions, Part 25. - Part 24: Effenberger, F., Kremser, A. and Stelzer, U. (1996) "A Convenient Synthesis of (S)-2-Azidonitriles, (S)-2-Aminonitriles and (S)-1,2-Diamines". Tetrahedron Asymmetry 7, 607-618.
    • (1996) Tetrahedron Asymmetry , vol.7 , pp. 607-618
    • Effenberger, F.1    Kremser, A.2    Stelzer, U.3
  • 2
    • 0019623877 scopus 로고
    • Enzyme catalyzed reactions in water-organic solvent two-phase systems
    • Antonini, E., Carrea, G. and Cremonesi, P. (1981) "Enzyme catalyzed reactions in water-organic solvent two-phase systems". Enzyme Microb. Technol. 3, 291-296.
    • (1981) Enzyme Microb. Technol. , vol.3 , pp. 291-296
    • Antonini, E.1    Carrea, G.2    Cremonesi, P.3
  • 3
    • 0020477017 scopus 로고
    • Stabilization of Protein Structure by Sugars
    • Arakawa, T. and Timasheff, S.N. (1982) "Stabilization of Protein Structure by Sugars". Biochemistry 21, 6536-6544.
    • (1982) Biochemistry , vol.21 , pp. 6536-6544
    • Arakawa, T.1    Timasheff, S.N.2
  • 4
    • 0017845938 scopus 로고
    • D-Hydroxynitrile Lyase: Involvement of the Prosthetic Flavin Adenine Dinucleotide in Enzyme Activity
    • Bärwald, K.-R. and Jaenicke, L. (1978) "D-Hydroxynitrile Lyase: Involvement of the Prosthetic Flavin Adenine Dinucleotide in Enzyme Activity". FEBS Lett. 90, 255-260.
    • (1978) FEBS Lett. , vol.90 , pp. 255-260
    • Bärwald, K.-R.1    Jaenicke, L.2
  • 5
    • 26444534746 scopus 로고    scopus 로고
    • (1969) "Verfahren und Katalysator zur Darstellung von Cyanhydrinen sowie Verfahren zur Darstellung des Katalysators". Dt. Pat. DE-OS 1593260
    • Becker, W. and Pfeil, E. (1969) "Verfahren und Katalysator zur Darstellung von Cyanhydrinen sowie Verfahren zur Darstellung des Katalysators". Dt. Pat. DE-OS 1593260.
    • Becker, W.1    Pfeil, E.2
  • 6
    • 26444433673 scopus 로고
    • Beitrag zur Kenntnis der ätherischen Öle, III. Mitteil.: Über sauerstoffhaltige Bestandteile des Citronellöls-Java
    • Bohnsack, H. (1943) "Beitrag zur Kenntnis der ätherischen Öle, III. Mitteil.: Über sauerstoffhaltige Bestandteile des Citronellöls-Java". Ber. Dtsch. Chem. Ges. 76, 564-572.
    • (1943) Ber. Dtsch. Chem. Ges. , vol.76 , pp. 564-572
    • Bohnsack, H.1
  • 7
    • 26444536047 scopus 로고
    • Dissertation, Universität Leiden
    • Brussee, J. (1992) Dissertation, p. 36. Universität Leiden.
    • (1992) , pp. 36
    • Brussee, J.1
  • 8
    • 0000875956 scopus 로고
    • Mechanism of Carbanion Addition to Carbonyl Compounds. Equilibria and Kinetics of Substituted Cyanohydrin Cleavage and Formation in Aqueous Solution. Substituted Cyanohydrin Proton Dissociation Constants
    • Ching, W.-M. and Kallen, R.G. (1978) "Mechanism of Carbanion Addition to Carbonyl Compounds. Equilibria and Kinetics of Substituted Cyanohydrin Cleavage and Formation in Aqueous Solution. Substituted Cyanohydrin Proton Dissociation Constants". J. Am. Chem. Soc. 100, 6119-6124.
    • (1978) J. Am. Chem. Soc. , vol.100 , pp. 6119-6124
    • Ching, W.-M.1    Kallen, R.G.2
  • 9
    • 0344853432 scopus 로고
    • A quantitative study of semicarbazone formation
    • Conant, J.B. and Bartlett, P.D. (1932) "A quantitative study of semicarbazone formation". J. Am. Chem. Soc. 54, 2881-2899.
    • (1932) J. Am. Chem. Soc. , vol.54 , pp. 2881-2899
    • Conant, J.B.1    Bartlett, P.D.2
  • 10
    • 33748215202 scopus 로고
    • Synthesis and Reactions of Optically Active Cyanohydrins
    • Effenberger, F. (1994) "Synthesis and Reactions of Optically Active Cyanohydrins". Angew. Chem. Int. Ed. Engl. 33, 1555-1564.
    • (1994) Angew. Chem. Int. Ed. Engl. , vol.33 , pp. 1555-1564
    • Effenberger, F.1
  • 11
    • 0024607278 scopus 로고
    • Extractive catalysis: Solvent effects on equilibria of enzymatic reactions in two-phase systems
    • Eggers, D.K., Blanch, H.W. and Prausnitz, J.M. (1989) "Extractive catalysis: solvent effects on equilibria of enzymatic reactions in two-phase systems". Enzyme Microb. Technol. 11, 84-89.
    • (1989) Enzyme Microb. Technol. , vol.11 , pp. 84-89
    • Eggers, D.K.1    Blanch, H.W.2    Prausnitz, J.M.3
  • 12
    • 26444515332 scopus 로고
    • (1993) "Enzymic manufacture of optically active cyanohydrins in a two-phase solvent system". Eur. Pat. Appl. EP 547, 655
    • Geluk, H.W. and Loos, W.T. (1993) "Enzymic manufacture of optically active cyanohydrins in a two-phase solvent system". Eur. Pat. Appl. EP 547, 655; Chem. Abstr. 119, 158357g (1993).
    • (1993) Chem. Abstr. , vol.119
    • Geluk, H.W.1    Loos, W.T.2
  • 13
    • 0029636165 scopus 로고
    • Enzyme Catalyzed Biotransformations in Aqueous Two-Phase Systems with Precipitated Substrate and/or Product
    • Kasche, V. and Galunsky, B. (1995) "Enzyme Catalyzed Biotransformations in Aqueous Two-Phase Systems with Precipitated Substrate and/or Product". Biotechnol. Bioeng. 45, 261-267.
    • (1995) Biotechnol. Bioeng. , vol.45 , pp. 261-267
    • Kasche, V.1    Galunsky, B.2
  • 14
    • 0027325846 scopus 로고
    • Aliphatic (S)-Cyanohydrins by Enzyme Catalyzed Synthesis
    • Klempier, N., Griengl, H. and Hayn, M. (1993) "Aliphatic (S)-Cyanohydrins by Enzyme Catalyzed Synthesis". Tetrahedron Lett. 34, 4769-4772.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 4769-4772
    • Klempier, N.1    Griengl, H.2    Hayn, M.3
  • 15
    • 0028964103 scopus 로고
    • Synthesis of α,β-unsaturated (S)-Cyanohydrins Using the Oxynitrilase from Hevea brasiliensis
    • Klempier, N., Pichler, U. and Griengl, H. (1995) "Synthesis of α,β-unsaturated (S)-Cyanohydrins Using the Oxynitrilase from Hevea brasiliensis" Tetrahedron Asymmetry 6, 845-848.
    • (1995) Tetrahedron Asymmetry , vol.6 , pp. 845-848
    • Klempier, N.1    Pichler, U.2    Griengl, H.3
  • 16
    • 0002968804 scopus 로고
    • Chiral Cyanohydrins - Their Manufacture and Utility as Chiral Building Blocks
    • edited by A.N. Collins, G.N. Sheldrake and J. Crosby, New York: Wiley
    • Kruse, C.G. (1992) "Chiral Cyanohydrins - Their Manufacture and Utility as Chiral Building Blocks". In Chirality in Industry, edited by A.N. Collins, G.N. Sheldrake and J. Crosby, pp. 279-299. New York: Wiley.
    • (1992) Chirality in Industry , pp. 279-299
    • Kruse, C.G.1
  • 17
    • 0000024542 scopus 로고
    • The Synthesis of 3-Hydroxy-2-(3)-benzofuranone and of 4-Hydroxymandelic Acid
    • Ladenburg, K., Folkers, K. and Major, R.T. (1936) "The Synthesis of 3-Hydroxy-2-(3)-benzofuranone and of 4-Hydroxymandelic Acid". J. Am. Chem. Soc. 58, 1292-1294.
    • (1936) J. Am. Chem. Soc. , vol.58 , pp. 1292-1294
    • Ladenburg, K.1    Folkers, K.2    Major, R.T.3
  • 19
    • 0019344592 scopus 로고
    • Two-liquid-phase Biocatalytic Reactions
    • Lilly, M.D. (1982) "Two-liquid-phase Biocatalytic Reactions". J. Chem. Tech. Biotechnol. 32, 162-169.
    • (1982) J. Chem. Tech. Biotechnol. , vol.32 , pp. 162-169
    • Lilly, M.D.1
  • 21
    • 37049073081 scopus 로고
    • Optically Active (S)-Ketone and (R)-Aldehyde-cyanohydrins via an (R)-Oxynitrilase-catalysed Transcyanation. Chemoenzymatic Syntheses of 2-Cyanotetrahydrofuran and 2-Cyanotetrahydropyran
    • Menéndez, E., Brieva, R., Rebolledo, F. and Gotor, V. (1995) "Optically Active (S)-Ketone and (R)-Aldehyde-cyanohydrins via an (R)-Oxynitrilase-catalysed Transcyanation. Chemoenzymatic Syntheses of 2-Cyanotetrahydrofuran and 2-Cyanotetrahydropyran". J. Chem. Soc., Chem. Commun. 989-990.
    • (1995) J. Chem. Soc., Chem. Commun. , pp. 989-990
    • Menéndez, E.1    Brieva, R.2    Rebolledo, F.3    Gotor, V.4
  • 22
    • 26444572130 scopus 로고
    • Dissertation, Universität Düsseldorf
    • Niedermeyer, U. (1989) Dissertation, Universität Düsseldorf.
    • (1989)
    • Niedermeyer, U.1
  • 23
    • 0025253111 scopus 로고
    • Enzyme-catalyzed Synthesis of (5)-Cyanohydrins
    • Niedermeyer, U. and Kula, M.-R. (1990) "Enzyme-catalyzed Synthesis of (5)-Cyanohydrins". Angew. Chem. Int. Ed. Engl. 29, 386-387.
    • (1990) Angew. Chem. Int. Ed. Engl. , vol.29 , pp. 386-387
    • Niedermeyer, U.1    Kula, M.-R.2
  • 24
    • 26444483685 scopus 로고
    • (1993) "Manufacture of chiral cyanohydrins by resolution with oxynitrilase". Ger. DE 4, 139, 987
    • Niedermeyer, U. (1993) "Manufacture of chiral cyanohydrins by resolution with oxynitrilase". Ger. DE 4, 139, 987; Chem. Abstr. 119, 70564m (1993).
    • (1993) Chem. Abstr. , vol.119
    • Niedermeyer, U.1
  • 25
    • 85064432185 scopus 로고
    • Catalytic Asymmetric Cyanohydrin Synthesis
    • North, M. (1993) "Catalytic Asymmetric Cyanohydrin Synthesis". Synlett, 807-820.
    • (1993) Synlett , pp. 807-820
    • North, M.1
  • 26
    • 0003033957 scopus 로고
    • Equilibrium additions to carbonyl compounds
    • edited by J. Zabicky, London: Interscience
    • Ogata, Y. and Kawasaki, A. (1970) "Equilibrium additions to carbonyl compounds". In The Chemistry of the Carbonyl Group, edited by J. Zabicky, Vol. 2, pp. 33-36. London: Interscience.
    • (1970) The Chemistry of the Carbonyl Group , vol.2 , pp. 33-36
    • Ogata, Y.1    Kawasaki, A.2
  • 27
    • 0002256381 scopus 로고
    • Condensations leading to double bonds
    • edited by S. Patai, London: Interscience
    • Reeves, R.L. (1966) "Condensations leading to double bonds". In The Chemistry of the Carbonyl Group, edited by S. Patai, Vol. 1, p. 606. London: Interscience.
    • (1966) The Chemistry of the Carbonyl Group , vol.1 , pp. 606
    • Reeves, R.L.1
  • 28
    • 0002883588 scopus 로고
    • Stabilized soluble enzymes
    • Schmid, R.D. (1979) "Stabilized soluble enzymes". Adv. Biochem. Eng. 12, 41-118.
    • (1979) Adv. Biochem. Eng. , vol.12 , pp. 41-118
    • Schmid, R.D.1
  • 29
    • 0018787705 scopus 로고
    • Mechanism of Catalysis by the Flavoenzyme Oxynitrilase
    • Schuman Jorns, M. (1979) "Mechanism of Catalysis by the Flavoenzyme Oxynitrilase". J. Biol. Chem. 254, 12145-12152.
    • (1979) J. Biol. Chem. , vol.254 , pp. 12145-12152
    • Schuman Jorns, M.1
  • 30
    • 26444502403 scopus 로고
    • Dissertation, Universität Stuttgart
    • Schwämmle, A. (1995) Dissertation, Universität Stuttgart.
    • (1995)
    • Schwämmle, A.1
  • 31
    • 0014011418 scopus 로고
    • The Metabolism of Aromatic Compounds in Higher Plants. VIII on the Requirement of Hydroxynitrile Lyase for Flavin
    • Seely, M.K., Criddle, R.S. and Conn, E.E. (1966) "The Metabolism of Aromatic Compounds in Higher Plants. VIII On the Requirement of Hydroxynitrile Lyase for Flavin". J. Biol. Chem. 241, 4457-4462.
    • (1966) J. Biol. Chem. , vol.241 , pp. 4457-4462
    • Seely, M.K.1    Criddle, R.S.2    Conn, E.E.3
  • 32
    • 0006981889 scopus 로고
    • Water-organic solvent two-phase systems as media for biocatalytic reactions
    • Semenov, A.N., Khmelnitski, Y.L., Berezin, I.V. and Martinek, K. (1987) "Water-organic solvent two-phase systems as media for biocatalytic reactions". Biocatalysis 1, 3-8.
    • (1987) Biocatalysis , vol.1 , pp. 3-8
    • Semenov, A.N.1    Khmelnitski, Y.L.2    Berezin, I.V.3    Martinek, K.4
  • 33
    • 0037525783 scopus 로고
    • Carbonyl Reactions.I. The Kinetics of Cyanohydrin Formation in Aqueous Solution
    • Svirbely, W.J. and Roth, J.F. (1953) "Carbonyl Reactions.I. The Kinetics of Cyanohydrin Formation in Aqueous Solution". J. Am. Chem. Soc. 75, 3106-3111.
    • (1953) J. Am. Chem. Soc. , vol.75 , pp. 3106-3111
    • Svirbely, W.J.1    Roth, J.F.2
  • 34
    • 26444540154 scopus 로고
    • (1993) "Enantiomeric enrichment of cyanohydrins". US Pat. 5,241,087
    • van Eikeren, P. (1993) "Enantiomeric enrichment of cyanohydrins". US Pat. 5,241,087: Chem. Abstr. 120, 8336f (1994).
    • (1994) Chem. Abstr. , vol.120
    • Van Eikeren, P.1
  • 35
    • 0028337630 scopus 로고
    • Purification of oxynitrilases from plants
    • Woker, R., Vernau, J. and Kula, M.-R. (1994) "Purification of oxynitrilases from plants". Methods Enzymol. 228, 584-590.
    • (1994) Methods Enzymol. , vol.228 , pp. 584-590
    • Woker, R.1    Vernau, J.2    Kula, M.-R.3


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