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Volumn 1, Issue 5, 2006, Pages 564-568

Operational concept for the improved synthesis of (R)-3,3'-furoin and related hydrophobic compounds with benzaldehyde lyase

Author keywords

Benzaldehyde lyase; Benzoin condensation; Biphasic media; Continuous synthesis; Fluidized bed

Indexed keywords

BENZALDEHYDE LYASE; BENZOIN CONDENSATION; BIPHASIC MEDIA; BIPHASIC REACTION; BIPHASIC SYSTEMS; CONTINUOUS OPERATION; CONTINUOUS PROCESS; CONTINUOUS SYNTHESIS; ENANTIOPURE; ENHANCED STABILITY; ENZYME CATALYSIS; FLUIDISED BED; HYDROPHOBIC COMPOUNDS; NON-AQUEOUS; OPERATION CONDITIONS; OPERATIONAL CONCEPTS; POLYMER BEADS; REACTION CONDITIONS; STABLE OPERATION;

EID: 33845548028     PISSN: 18606768     EISSN: 18607314     Source Type: Journal    
DOI: 10.1002/biot.200600030     Document Type: Article
Times cited : (20)

References (27)
  • 1
    • 0034982692 scopus 로고    scopus 로고
    • Enantioselective synthesis of hydroxyl ketones through cleavage and formation of acyloin linkage. Enzymatic kinetic resolution via C-C bond cleavage
    • Demir, A. S., Pohl, M., Janzen, E., Müller, M., Enantioselective synthesis of hydroxyl ketones through cleavage and formation of acyloin linkage. Enzymatic kinetic resolution via C-C bond cleavage. J. Chem. Soc. Perkin Trans. 2001, 1, 633-635.
    • (2001) J. Chem. Soc. Perkin Trans. , vol.1 , pp. 633-635
    • Demir, A.S.1    Pohl, M.2    Janzen, E.3    Müller, M.4
  • 2
    • 4744350097 scopus 로고    scopus 로고
    • Enantioselective synthesis of alpha-hydroxy ketones via benzaldehyde lyase-catalyzed C-C bond formation reaction
    • Demir, A. S., Sesenoglu, O., Eren, E., Hosrik, B. et al., Enantioselective synthesis of alpha-hydroxy ketones via benzaldehyde lyase-catalyzed C-C bond formation reaction. Adv. Synth. Catal. 2002, 344, 96-103.
    • (2002) Adv. Synth. Catal. , vol.344 , pp. 96-103
    • Demir, A.S.1    Sesenoglu, O.2    Eren, E.3    Hosrik, B.4
  • 3
    • 0242526077 scopus 로고    scopus 로고
    • Mixed aromatic acyloin condensations with recombinant benzaldehyde lyase: synthesis of alpha-hydroxydihydrochalcones and related alpha-hydroxy ketones
    • Sanchez-Gonzalez, M., Rosazza, J. P. N., Mixed aromatic acyloin condensations with recombinant benzaldehyde lyase: synthesis of alpha-hydroxydihydrochalcones and related alpha-hydroxy ketones. Adv. Synth. Catal. 2003, 345, 819-824.
    • (2003) Adv. Synth. Catal. , vol.345 , pp. 819-824
    • Sanchez-Gonzalez, M.1    Rosazza, J.P.N.2
  • 4
    • 0037120881 scopus 로고    scopus 로고
    • Development of a donor-acceptor concept for enzymatic cross-coupling reactions of aldehydes: The first asymmetric cross-benzoin condensation
    • Dünkelmann, P., Kolter-Jung, D., Nitsche, A., Demir, A. S. et al., Development of a donor-acceptor concept for enzymatic cross-coupling reactions of aldehydes: The first asymmetric cross-benzoin condensation. J. Am. Chem. Soc. 2002, 124, 12084-12085.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 12084-12085
    • Dünkelmann, P.1    Kolter-Jung, D.2    Nitsche, A.3    Demir, A.S.4
  • 5
    • 21744459715 scopus 로고    scopus 로고
    • Stereoselective synthesis of novel benzoins catalysed by benzaldehyde lyase in a gel-stabilised two-phase system
    • Hischer, T., Gocke, D., Fernandez, M., Hoyos, P. et al., Stereoselective synthesis of novel benzoins catalysed by benzaldehyde lyase in a gel-stabilised two-phase system. Tetrahedron 2005, 61, 7378-7383.
    • (2005) Tetrahedron , vol.61 , pp. 7378-7383
    • Hischer, T.1    Gocke, D.2    Fernandez, M.3    Hoyos, P.4
  • 6
    • 0027265466 scopus 로고
    • Synthesis of 10-Deacetoxytaxol and 10-Deoxytaxotere
    • Chaudhary, A. G., Kingston, D. G. I., Synthesis of 10-Deacetoxytaxol and 10-Deoxytaxotere. Tetrahedron Lett. 1993, 34, 4921-4924.
    • (1993) Tetrahedron Lett , vol.34 , pp. 4921-4924
    • Chaudhary, A.G.1    Kingston, D.G.I.2
  • 7
    • 0029860827 scopus 로고    scopus 로고
    • Kurasoins A and B, new protein farnesyltransferase inhibitors produced by Paecilomyces sp FO-3684. II. Structure elucidation and total synthesis
    • Uchida, R., Shiomi, K., Sunazuka, T., Inokoshi, J. et al., Kurasoins A and B, new protein farnesyltransferase inhibitors produced by Paecilomyces sp. FO-3684. II. Structure elucidation and total synthesis. J. Antibiotics 1996, 49, 886-889.
    • (1996) J. Antibiotics , vol.49 , pp. 886-889
    • Uchida, R.1    Shiomi, K.2    Sunazuka, T.3    Inokoshi, J.4
  • 8
    • 0029791485 scopus 로고    scopus 로고
    • Studies on the synthesis of aureolic acid antibiotics: acyloin glycosidation studies
    • Roush, W. R., Briner, K., Kesler, B. S., Murphy, M., Gustin, D. J., Studies on the synthesis of aureolic acid antibiotics: acyloin glycosidation studies. J. Org. Chem. 1996, 61, 6098-6099.
    • (1996) J. Org. Chem. , vol.61 , pp. 6098-6099
    • Roush, W.R.1    Briner, K.2    Kesler, B.S.3    Murphy, M.4    Gustin, D.J.5
  • 9
    • 0001578860 scopus 로고    scopus 로고
    • Nitridomanganese(V) complexes: design, preparation, and use as nitrogen atom-transfer reagents
    • Du Bois, J., Tomooka, C. S., Hong, J., Carreira, E. M., Nitridomanganese(V) complexes: design, preparation, and use as nitrogen atom-transfer reagents. Acc. Chem. Res. 1997, 30, 364-372.
    • (1997) Acc. Chem. Res. , vol.30 , pp. 364-372
    • Du Bois, J.1    Tomooka, C.S.2    Hong, J.3    Carreira, E.M.4
  • 10
    • 0032557705 scopus 로고    scopus 로고
    • Synthesis and Rhizopus oryzae mediated enantioselective hydrolysis of 〈 -acetoxy aryl alkyl ketones
    • Demir, A. S., Hamamci, H., Tanyeli, C., M.Akhmedov, I., Doganel, F., Synthesis and Rhizopus oryzae mediated enantioselective hydrolysis of 〈 -acetoxy aryl alkyl ketones. Tetrahedron Asymm. 1998, 9, 1673-1677.
    • (1998) Tetrahedron Asymm , vol.9 , pp. 1673-1677
    • Demir, A.S.1    Hamamci, H.2    Tanyeli, C.3    Akhmedov, M.I.4    Doganel, F.5
  • 11
    • 0033230416 scopus 로고    scopus 로고
    • Alpha-trifluoromethylated acyloins induce apoptosis in human oral tumor cell lines
    • Kawase, M., Sakagami, H., Kusama, K., Motohashi, N., Saito, S., Alpha-trifluoromethylated acyloins induce apoptosis in human oral tumor cell lines. Bioorg. Med. Chem. Lett. 1999, 9, 3113-3118.
    • (1999) Bioorg. Med. Chem. Lett. , vol.9 , pp. 3113-3118
    • Kawase, M.1    Sakagami, H.2    Kusama, K.3    Motohashi, N.4    Saito, S.5
  • 12
    • 0033582467 scopus 로고    scopus 로고
    • A simple procedure for the synthesis of enantiopure 〈 -acetoxy ketones
    • Babudri, F., Fiandanese, V., Marchese, G., Punzi, A. A simple procedure for the synthesis of enantiopure 〈 -acetoxy ketones. Tetrahedron 1999, 55, 2431-2440.
    • (1999) Tetrahedron , vol.55 , pp. 2431-2440
    • Babudri, F.1    Fiandanese, V.2    Marchese, G.3    Punzi, A.4
  • 14
    • 0032736221 scopus 로고    scopus 로고
    • Biocatalytic synthesis of optically active r-oxyfunctionalized carbonyl compounds
    • Adam, W., Lazarus, M., Saha-Möller, C. R., Schreier, P., Biocatalytic synthesis of optically active r-oxyfunctionalized carbonyl compounds. Acc. Chem. Res. 1999, 32, 837-845.
    • (1999) Acc. Chem. Res. , vol.32 , pp. 837-845
    • Adam, W.1    Lazarus, M.2    Saha-Möller, C.R.3    Schreier, P.4
  • 15
    • 0034703153 scopus 로고    scopus 로고
    • Rapid access to enantiopure bupropion and its major metabolite by stereospecific nucleophilic substitution on a-ketotriflate
    • Fang, Q. K., Han, Z., Grover, P., Kessler, D. et al., Rapid access to enantiopure bupropion and its major metabolite by stereospecific nucleophilic substitution on a-ketotriflate. Tetrahedron Asymm. 2000, 11, 3659-3663.
    • (2000) Tetrahedron Asymm , vol.11 , pp. 3659-3663
    • Fang, Q.K.1    Han, Z.2    Grover, P.3    Kessler, D.4
  • 16
    • 0037463802 scopus 로고    scopus 로고
    • Inhibitors of Abeta production: solid-phase synthesis and SAR of alpha-hydroxycarbonyl derivatives
    • Wallace, O. B., Smith, D. W., Deshpande, M. S., Polson, C., Felsenstein, K. M., Inhibitors of Abeta production: solid-phase synthesis and SAR of alpha-hydroxycarbonyl derivatives. Bioorg. Med. Chem. Lett. 2003, 13, 1203.
    • (2003) Bioorg. Med. Chem. Lett. , vol.13 , pp. 1203
    • Wallace, O.B.1    Smith, D.W.2    Deshpande, M.S.3    Polson, C.4    Felsenstein, K.M.5
  • 19
    • 0021170291 scopus 로고
    • Biocatalysis in water-organic solvent two-phase systems
    • Carrea, G., Biocatalysis in water-organic solvent two-phase systems. Trends Biotechnol. 1984, 2, 102-106.
    • (1984) Trends Biotechnol , vol.2 , pp. 102-106
    • Carrea, G.1
  • 20
    • 0035024562 scopus 로고    scopus 로고
    • Synthesis of optically pure ethyl (S)-4-chloro-3-hydroxybutanoate by Escherichia coli transformant cells coexpressing the carbonyl reductase and glucose dehydrogenase genes
    • Kizaki, N., Yasohara, Y., Hasegawa, J., Wada, M. et al., Synthesis of optically pure ethyl (S)-4-chloro-3-hydroxybutanoate by Escherichia coli transformant cells coexpressing the carbonyl reductase and glucose dehydrogenase genes. Appl. Microbiol. Biotechnol. 2001, 55, 590-595.
    • (2001) Appl. Microbiol. Biotechnol. , vol.55 , pp. 590-595
    • Kizaki, N.1    Yasohara, Y.2    Hasegawa, J.3    Wada, M.4
  • 21
    • 0037666071 scopus 로고    scopus 로고
    • Practical asymmetric enzymatic reduction through discovery of a dehydrogenase-compatible biphasic reaction media
    • Gröger, H., Hummel, W., Buchholz, S., Drauz, K. et al., Practical asymmetric enzymatic reduction through discovery of a dehydrogenase-compatible biphasic reaction media. Org. Lett. 2003, 5, 173-176.
    • (2003) Org. Lett. , vol.5 , pp. 173-176
    • Gröger, H.1    Hummel, W.2    Buchholz, S.3    Drauz, K.4
  • 22
    • 21744445662 scopus 로고    scopus 로고
    • Application of alpha-keto acid decarboxylases in biotransformations
    • Iding, H., Dünnwald, T., Greiner, L., Liese, A. et al., Application of alpha-keto acid decarboxylases in biotransformations. Eur. J. Biochem. 1998, 257, 538-546.
    • (1998) Eur. J. Biochem. , vol.257 , pp. 538-546
    • Iding, H.1    Dünnwald, T.2    Greiner, L.3    Liese, A.4
  • 23
    • 0345829160 scopus 로고    scopus 로고
    • Utilization of adsorption effects for the continuous reduction of NADP+ with molecular hydrogen using Pyrococcus furiosus hydrogenase
    • Greiner, L., Schröder, I., Müller, D. H., Liese, A., Utilization of adsorption effects for the continuous reduction of NADP+ with molecular hydrogen using Pyrococcus furiosus hydrogenase. Green Chem. 2003, 5, 697-700.
    • (2003) Green Chem , vol.5 , pp. 697-700
    • Greiner, L.1    Schröder, I.2    Müller, D.H.3    Liese, A.4
  • 24
    • 85023335044 scopus 로고
    • The behaviour of proteins in relation to their structural stability
    • van den Tweel, W. J., Harder, A., Buitelaar, R. M. (Eds.), Elsevier, Amsterdam
    • Norde, W., The behaviour of proteins in relation to their structural stability, in: van den Tweel, W. J., Harder, A., Buitelaar, R. M. (Eds.), Stability and Stabilisation of Enzymes. Elsevier, Amsterdam 1993, pp. 3-11.
    • (1993) Stability and Stabilisation of Enzymes , pp. 3-11
    • Norde, W.1
  • 25
    • 0028371139 scopus 로고
    • Inactivation of enzymes by organic solvents: new technique with well-defined interfacial area
    • Ghatorae, A. S., Bell, G., Halling, P. J., Inactivation of enzymes by organic solvents: new technique with well-defined interfacial area. Biotech. Bioeng. 1994, 43, 331-336.
    • (1994) Biotech. Bioeng. , vol.43 , pp. 331-336
    • Ghatorae, A.S.1    Bell, G.2    Halling, P.J.3
  • 26
    • 0023289451 scopus 로고
    • Atomic physicochemical parameters for three-dimensional-structure-directed quantitative structureactivity relationships. 2. Modeling dispersive and hydrophobic interactions
    • Ghose, A. K., Crippen, G. M. J., Atomic physicochemical parameters for three-dimensional-structure-directed quantitative structureactivity relationships. 2. Modeling dispersive and hydrophobic interactions. J. Chem. Inf. Comput. Sci. 1987, 27, 21-35.
    • (1987) J. Chem. Inf. Comput. Sci. , vol.27 , pp. 21-35
    • Ghose, A.K.1    Crippen, G.M.J.2
  • 27
    • 0032516289 scopus 로고    scopus 로고
    • Preparation and properties of unsymmetrical benzoins and related compounds
    • Corrie, J. E. T., Preparation and properties of unsymmetrical benzoins and related compounds. Tetrahedron 1998, 54, 5407-5416.
    • (1998) Tetrahedron , vol.54 , pp. 5407-5416
    • Corrie, J.E.T.1


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