Recent Advances in Biocatalysis Applied to Organic Synthesis

Catalytic Methods in Asymmetric Synthesis: Advanced Materials, Techniques, and Applications

Volumn , Issue , 2011, Pages 491-527

  de Gonzalo, Gonzalo ^a   Lavandera, Iván ^a   Gotor, Vicente ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

Biocatalysis, recent advances biological methods, tool for stereo and regioselective transformations; Recent biocatalyzed methodologies, lyases EC 4.X.X.X biocatalysts, small molecules to double bonds "L" in small capital, please; Transferases, enzyme types transference of one group into another one, aminotransferases

Indexed keywords

EID: 84885964127     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9781118087992.ch12     Document Type: Chapter

References (106)

1. Breuer, M., Ditrich, K., Habicher, T., Hauer, B., Kesseler, M., Stürmer, R., Zelinski, T. (2004). Industrial methods for the production of optically active intermediates. Angew. Chem. Int. Ed., 43, 788-824.
2. Anastas, P., Eghbali, N. (2010). Green chemistry: principles and practice. Chem. Soc. Rev., 39, 301-312.
3. Fessner, W. D., Anthonsen, T. (2009). Modern Biocatalysis: Stereoselective and Environmentally Friendly Reactions. Wiley-VCH, Weinheim, Germany.
4. Gotor, V., Alfonso, I., García-Urdiales, E. (2008). Asymmetric Organic Synthesis with Enzymes. Wiley-VCH, Weinheim, Germany.
5. Patel, R. N. (Ed.) (2007). Biocatalysis in the Pharmaceutical and Biotechnology Industry. CRC Press, Boca Raton, FL.
6. Faber, K. (2004). Biotransformations in Organic Chemistry, 5th ed., Springer, Berlin, Germany.
7. Hudlicky, T., Reed, J. W. (2009). Applications of biotransformations and biocatalysis to complexity generation in organic synthesis. Chem. Soc. Rev., 38, 3117-3132.
8. Schmid, R. D., Urlacher, V. B. (2007). Modern Biooxidation. Enzymes, Reactions and Applications, Wiley-VCH, Weinheim, Germany.
9. Huisman, G. W., Liang, J., Krebber, A. (2010). Practical chiral alcohol manufacture using ketoreductases. Curr. Opin. Chem. Biol., 14, 122-129.
10. Matsuda, T., Yamanaka, R., Nakamura, K. (2009). Recent progress in biocatalysis for asymmetric oxidation and reduction. Tetrahedron: Asymmetry, 20, 513-557.
11. de Wildeman, S. M. A., Sonke, T., Schoemaker, H. E., May, O. (2007). Biocatalytic reductions: from lab curiosity to "fi rst choice." Acc. Chem. Res., 40, 1260-1266.
12. de Gonzalo, G., Lavandera, I., Faber, K., Kroutil, W. (2007). Enzymatic reduction of ketones in "micro-aqueous" media catalyzed by ADH-A from Rhodococcus ruber. Org. Lett., 9, 2163-2166.
13. Hildebrand, F., Lütz, S. (2009). Stable electroenzymatic processes by catalyst separation. C hem. Eur. J., 15, 4998-5001.
14. Bisogno, F. R., Lavandera, I., Kroutil, W., Gotor, V. (2009). Tandem concurrent processes: one-pot single-catalyst biohydrogen transfer for the simultaneous preparation of enantiopure secondary alcohols. J. Org. Chem., 74, 1730-1732.
15. Edegger, K., Stampfer, W., Seisser, B., Faber, K., Mayer, S. F., Oerhrlein, R., Hafner, A., Kroutil, W. (2006). Regio-and stereoselective reduction of diketones and oxidation of diols by biocatalytic hydrogen transfer. Eur. J. Org. Chem., 1904-1909.
16. Kurina-Sanz, M., Bisogno, F. R., Lavandera, I., Orden, A. A., Gotor, V. (2009). Promiscuous substrate binding explains the enzymatic stereo-and regiocontrolled synthesis of enantiopure hydroxy ketones and diols. Adv. Synth. Catal., 351, 1842-1848.
17. Katzberg, M., Wechler, K., Müller, M., Dünkelmann, P., Stohrer, J., Hummel, W., Bertau, M. (2009). Biocatalytic production of (5 S)-hydroxy-2-hexanone. Org. Biomol. Chem., 7, 304-314.
18. Kalaitzakis, D., Rozzell, J. D., Kambourakis, S., Smonou, I. (2006). Synthesis of valuable chiral intermediates by isolated ketoreductases: synthesis of a-alkyl-ß- hydroxyketones and 1,3-diols. Adv. Synth. Catal., 348, 1958-1969.
19. Kalaitzakis, D., Rozzell, J. D., Kambourakis, S., Smonou, I. (2006). A two-step chemoenzymatic synthesis of the natural pheromone (+)-sitophilure utilizing isolated, NADPH-dependent ketoreductases. Eur. J. Org. Chem., 2309-2313.
20. Baer, K., Kraußer, M., Burda, E., Hummel, W., Berkessel, A., Gröger, H. (2009). Sequential and modular synthesis of chiral 1,3-diols with two sterogenic centers: access to all four stereoisomers by combination of organo-and biocatalysis. Angew. Chem. Int. Ed., 48, 9355-9358.
21. Gröger, H., Chamouleau, F., Orologas, N., Rollmann, C., Drauz, K., Hummel, W., Weckbecker, A., May, O. (2006). Enantioselective reduction of ketones with " designer cells" at high substrate concentrations: highly effi cient access to functionalized optically active alcohols. Angew. Chem. Int. Ed., 45, 5677-5681.
22. Zhu, D., Ankati, H., Mukherjee, C., Yang, Y., Biehl, E. R., Hua, L. (2007). Asymmetric reduction of ß-ketonitriles with a recombinant carbonyl reductase and enzymatic transformation to optically pure ß-hydroxy carboxylic acids. Org. Lett., 9, 2561-2563.
23. Ankati, H., Yang, Y., Zhu, D., Biehl, E. R., Hua, L. (2008). Synthesis of optically pure 2-azido-1-arylethanols with isolated enzymes and conversion of triazole - containing ß-blocker analogues employing click chemistry. J. Org. Chem., 73, 6433-6436.
24. Schrittwieser, J. H., Lavandera, I., Seisser, B., Mautner, B., Kroutil, W. (2009). Biocatalytic cascade for the synthesis of enantiopure ß-azidoalcohols andß- hydroxynitriles. Eur. J. Org. Chem., 2293-2298.
25. Guo, Z., Chen, Y., Goswami, A., Hanson, R. L., Patel, R. N. (2006). Synthesis of ethyl and t-butyl (3 R ,5 S)-dihydroxy-6-benzyloxy hexanoates via diastereo-and enantioselective microbial reduction. Tetrahedron: Asymmetry, 17, 1589-1602.
26. Milagre, H. M. S., Milagre, C. D. F., Moran, P. J. S., Santana, M. H. A., Rodrigues, J. A. R. (2006). Asymmetric bioreduction of ethyl 3-halo-2-oxo-4-phenylbutanoate by Saccharomyces cerevisiae immobilized in Ca-alginate beads with double gel layer. Org. Process Res. Dev., 10, 611-617.
27. Acetti, D., Brenna, E., Fuganti, C. (2007). A new enzymatic approach to (R) - tamsulosin hydrochloride. Tetrahedron: Asymmetry, 18, 488-492.
28. Fischer, T., Pietruszka, J. (2007). Effi cient synthesis of either enantiomer of ethyl 5-hydroxyhept-6-enoate. Adv. Synth. Catal., 349, 1533-1536.
29. Matsuda, M., Yamazaki, T., Fuhshuku, K., Sugai, T. (2007). First total synthesis of modiolide A, based on the whole-cell yeast-catalyzed asymmetric reduction of a propargyl ketone. Tetrahedron, 63, 8752-8760.
30. Ema, T., Ide, S., Okita, N., Sakai, T. (2008). Highly effi cient chemoenzymatic synthesis of methyl (R)-o-chloromandelate, a key intermediate for clopidogrel, via asymmetric reduction with recombinant Escherichia coli. Adv. Synth. Catal., 350, 2039-2044.
31. Broussy, S., Cheloha, R. W., Berkowitz, D. B. (2009). Enantioselective ketoreductases-based entry into pharmaceutical building blocks: ethanol as tunable nicotinamide reductant. Org. Lett., 11, 305-308.
32. Vieira, G. A. B., Lemos, T. L. G., de Mattos, M. C., de Oliveira, M. C. F., Melo, V. M. M., de Gonzalo, G., Gotor-Fernández, V., Gotor, V. (2009). Chemoenzymatic synthesis of optically active mugetanol isomers: use of lipases and oxidoreductases in fragrance chemistry. Tetrahedron: Asymmetry, 20, 214-219.
33. Lacheretz, R., Gomez Pardo, D., Cossy, J. (2009). Daucus carota mediated - reduction of cyclic 3-oxo-amines. Org. Lett., 11, 1245-1248.
34. Voss, C. V., Gruber, C. C., Kroutil, W. (2008). Deracemization of secondary alcohols through tandem biocatalytic oxidation and reduction. Angew. Chem. Int. Ed., 47, 741-745.
35. Voss, C. V., Gruber, C. C., Faber, K., Knaus, T., Macheroux, P., Kroutil, W. (2008). Orchestration of concurrent oxidation and reduction cycles for stereoinversion and deracemisation of sec-alcohols. J. Am. Chem. Soc., 130, 13969-13972.
36. Stuermer, R., Hauer, B., Hall, M., Faber, K. (2007). Asymmetric bioreduction of activated C = C bonds using enoate reductases from the old yellow enzyme family. Curr. Opin. Chem. Biol., 11, 203-213.
37. Hall, M., Stueckler, C., Kroutil, W., Macheroux, P., Faber, K. (2007). Asymmetric bioreduction of activated alkenes using cloned 12-oxophytodienoate reductase isoenzymes OPR-1 and OPR-3 from Lycopersicum esculentum (tomato): a striking change of stereoselectivity. Angew. Chem. Int. Ed., 46, 3934-3937.
38. Hall, M., Stueckler, C., Ehammer, H., Pointner, E., Oberdorfer, G., Gruber, K., Hauer, B., Stuermer, R., Kroutil, W., Macheroux, P., Faber, K. (2008). Asymmetric bioreduction of C = C bonds using enoate reductases OPR1, OPR3 and YqjM: enzyme-based stereocontrol. A dv. Synth. Catal., 3 50, 411-418.
39. Bougioukou, D. J., Stewart, J. D. (2008). Opposite stereochemical courses for enzyme-mediated alkene reductions of an enantiomeric pair substrate. J. Am. Chem. Soc., 130, 7655-7658.
40. Kosjek, B., Fleitz, F. J., Dormer, P. G., Kuethe, J. T., Devine, P. N. (2008). Asymmetric bioreduction of a, ß-unsaturated nitriles and ketones. Tetrahedron: Asymmetry, 19, 1403-1406.
41. Urlacher, V. B., Eiben, S. (2006). Cytochrome P450 monooxygenases: perspectives for synthetic application. Trends Biotechnol., 24, 324-330.
42. Bernhardt, R. (2006). Cytochromes P450 as versatile biocatalysts. J. Biotechnol., 124, 128-145.
43. Weis, R., Winkler, M., Schittmayer, M., Kambourakis, S., Vink, M., Rozzell, J. D., Glieder, A. (2009). A diversifi ed library of bacterial and fungal bifunctional cytochrome P450 enzymes for drug metabolite synthesis. Adv. Synth. Catal., 351, 2140-2146.
44. Alphand, V., Fraaije, M. W., Mihovilovic, M. D., Ottolina, G. (2009). Second generation Baeyer-Villiger biocatalysts. In: W. D. Fessner, T. Anthonsen Modern Biocatalysis: Stereoselective and Environmentally Friendly Reactions, Wiley-VCH, Weinheim, Germany, pp. 339-368.
45. Kayser, M. M. (2009). "Designer reagents" recombinant microorganisms: new and powerful tools for organic synthesis. Tetrahedron, 65, 947-974.
46. Rudroff, F., Rydz, J., Ogink, F. H., Fink, M., Mihovilovic, M. D. (2007). Comparing the stereoselective biooxidation of cyclobutanones by recombinant strains expressing bacterial Baeyer-Villiger monooxygenases. Adv. Synth. Catal., 349, 1436-1444.
47. Snajdrova, R., Braun, I., Bach, T., Mereiter, K., Mihovilovic, M. D. (2007). Biooxidation of bridged cycloketones using Baeyer-Villiger monooxygenases of various bacterial origin. J. Org. Chem., 72, 9597-9603.
48. Rodríguez, C., de Gonzalo, G., Fraaije, M. W., Gotor, V. (2007). Enzymatic kinetic resolution of racemic ketones catalyzed by Baeyer-Villiger monooxygenases. Tetrahedron: Asymmetry, 18, 1338-1344.
49. Rodríguez, C., de Gonzalo, G., Torres Pazmiño, D. E., Fraaije, M. W., Gotor, V. (2009). Baeyer-Villiger monooxygenase-catalyzed kinetic resolution of racemic a-alkyl benzyl ketones: enzymatic synthesis of a-alkyl benzylketones and a-alkyl benzylesters. Tetrahedron: Asymmetry, 20, 1168-1173.
50. Rioz-Martínez, A., Bisogno, F. R., Rodríguez, C., de Gonzalo, G., Lavandera, I., Torres Pazmiño, D. E., Fraaije, M. W., Gotor, V. (2010). Biocatalysed concurrent production of enantioenriched compounds through parallel interconnected kinetic asymmetric transformations. Org. Biomol. Chem., 8, 1431-1437.
51. Hudlicky, T., Reed, J. W. (2009). On the merits of biocatalysis and the impact of arene cis-dihydrodiols on enantioselective synthesis. Synlett, 685-703.
52. Sullivan, B., Carrera, I., Drouin, M., Hudlicky, T. (2009). Symmetry-based design for the chemoenzymatic synthesis of oseltamivir (Tamifl u) from ethyl benzoate. Angew. Chem. Int. Ed., 48, 4229-4231.
53. Turner, N. J. (2010). Deracemisation methods. Curr. Opin. Chem. Biol., 14, 115-121.
54. Bailey, K. R., Ellis, A. J., Reiss, R., Snape, T. J., Turner, N. J. (2007). A template based mnemonic for monoamine oxidase (MAO-N) catalyzed reactions and its application to the chemo-enzymatic deracemisation of the alkaloid (±)-crispine A. Chem. Commun., 3640-3642.
55. Riva, S. (2006). Laccases: blue enzymes for green chemistry. Trends Biotechnol., 24, 219-226.
56. Torre, O., Alfonso, I., Gotor, V. (2004). Lipase catalyzed Michael addition of secondary amines to acrylonitrile. Chem. Commun., 1724-1726.
57. Witayakran, S., Ragauskas, A. J. (2009). Cocatalytic enzyme system for the Michael reaction in-situ generated ortho-quinones. Eur. J. Org. Chem., 358-363.
58. Koszelewski, D., Tauber, K., Faber, K., Kroutil, W. (2010). ?-Transaminases for the synthesis of non-racemic a-chiral primary amines. Trends Biotechnol., 28, 324-332.
59. Koszelewski, D., Lavandera, I., Clay, D., Guebitz, G. M., Rozzell, D., Kroutil, W. (2008). Formal asymmetric biocatalytic reductive amination. Angew. Chem. Int. Ed., 47, 9337-9340.
60. Koszelewski, D., Pressnitz, D., Clay, D., Kroutil, W. (2009). Deracemization of mexiletine biocatalyzed by ?-transaminases. Org. Lett., 11, 4810-4812.
61. Ingram, C. U., Bommer, M., Smith, M. E. B., Dalby, P. A., Ward, J. M., Hailes, H. C., Lye, G. J. (2007). One-Pot synthesis of amino-alcohols using a de-novo transketolase and ß-alanine:pyruvate transaminase pathway in Escherichia coli. Biotechnol. Bioeng., 96, 559-569.
62. Bornscheuer, U. T., Kaszlauskas, R. S. (2005). Hydrolases in Organic Synthesis: Regio-and Stereoselective Biotransformations, Wiley-VCH, Weinheim, Germany.
63. Ghanem, A. (2007). Trends in lipase-catalyzed asymmetric access to enantiomerically pure/enriched compounds. Tetrahedron, 63, 1721-1754.
64. Mendiola, J., García-Cerrado, S., de Frutos, O., Puente, M. L., Gu, R. L., Khau, V. V. (2009). Enzymatic resolution of N-substituted-ß-prolines. Org. Process Res. Dev., 13, 292-296.
65. Patterson, L. D., Miller, M. J. (2010). Enzymatic deprotection of the cephalosporin 3 '-acetoxy group using Candida antarctica lipase B. J. Org. Chem., 75, 1289-1292.
66. Henke, E., Bornscheuer, U. T., Schmid, R. D., Pleiss, J. (2003). A molecular mechanism of enantiorecognition of tertiary alcohols by carboxylesterases. ChemBioChem, 4, 485-493.
67. Bartsch, S., Kourist, R., Bornscheuer, U. T. (2008). Complete inversion of enantioselectivity towards acetylated tertiary alcohols by a double mutation of a Bacillus subtilis esterase. Angew. Chem. Int. Ed., 47, 1508-1511.
68. Kourist, R., Nguyen, G.-S., Strübing, D., Böttcher, D., Liebeton, K., Naumer, C., Eck, J., Bornscheuer, U. T. (2008). Hydrolase-catalyzed stereoselective preparation of protected a, a-dialkyl-a-hydroxycarboxylic acids. Tetrahedron: Asymmetry, 19, 1839-1843.
69. Li, D., Cheng, S., Wei, D., Ren, Y., Zhang, D. (2007). Production of enantiomerically pure (S)-ß-phenylalanine and (R)-ß-phenylalanine by penicillin G acylase from Escherichia coli in aqueous medium. Biotechnol. Lett., 29, 1825-1830.
70. Heck, T., Seebach, D., Osswald, S., ter Wiel, M. K. J., Kholer, H.-P. E., Geueke, B. (2009). Kinetic resolution of aliphatic ß-amino acid amides by ß-aminopeptidases. ChemBioChem., 10, 1558-1561.
71. Forró E., Fülöp, F. (2007). The fi rst directed enzymatic hydrolysis of alicyclicß- amino acid esters: a route to enantiopure cis-and trans-ß-amino acids. Chem. Eur. J., 13, 6397-6401.
72. Tasnádi, G., Forró, E., Fülöp, F. (2008). An effi cient new enzymatic method for the preparation of ß-aryl-ß-amino acid enantiomers. Tetrahedron: Asymmetry, 19, 2072-2077.
73. Zutter, U., Iding, H., Spurr, P., Wirz, B. (2008). New, effi cient synthesis of oseltamivir phosphate (Tamifl u) via enzymatic desymmetrization of a meso-1,3 - cyclohexanedicarboxylic acid diester. J. Org. Chem., 73, 4895-4902.
74. Ríos-Lombardía, N., Busto, E., García-Urdiales, E., Gotor-Fernández, V., Gotor, V. (2009). Enzymatic desymmetrization of prochiral 2-substituted-1,3-diamines: preparation of valuable nitrogenated compounds. J. Org. Chem., 74, 2571-2574.
75. Gotor, V. (2009). Biocatalysis applied to the synthesis of nucleoside analogs. In: W. D. Fessner, T. Anthonsen Modern Biocatalysis: Stereoselective and Environmentally Friendly Reactions, Wiley-VCH, Weinheim, Germany, pp. 135-152.
76. Simeó, Y., Sinisterra, J. V., Alcántara, A. R. (2009). Regioselective enzymatic acylation of pharmacologically interesting nucleosides in 2-methyltetrahydrofuran, a greener substitute for THF. Green Chem., 11, 855-862.
77. Díaz-Rodríguez, A., Fernández, S., Sanghvi, Y. S., Ferrero, M., Gotor, V. (2006). Novel chemoenzymatic protocol for the synthesis of 3 '-O-dimethoxytrityl-2' - deoxynucleoside derivatives as building blocks for oligonucleotide synthesis. Org. Process Res. Dev., 10, 581-587.
78. Lee, J. H., Han, K., Kim, M.-J., Park, J. (2010). Chemoenzymatic dynamic kinetic resolution of alcohols and amines. Eur. J. Org. Chem., 999-1015.
79. Kamal, A., Azhar, M. A., Krishnaji, T., Malik, M. S., Azeeza, S. (2008). Approaches based on enzyme mediated kinetic to dynamic kinetic resolutions: a versatile route for chiral intermediates. Coord. Chem. Rev., 252, 569-592.
80. Suárez-Mangas, J., Rodríguez-Mata, M., Busto, E., Gotor-Fernández, V., Gotor, V. (2009). Chemoenzymatic synthesis of rivastigmine based on lipase-catalyzed processes. J. Org. Chem., 74, 5304-5310.
81. Kim, M.-J., Kim, W.-H., Han, K., Choi, Y. K., Park, J. (2007). Dynamic kinetic resolution of primary amines with a recyclable Pd nanocatalyst for racemization. Org. Lett., 9, 1157-1159.
82. Thalen, L. K., Zhao, D., Sortais, J.-B., Paetzold, J., Hoben, C., Bäckvall, J.-E. (2009). A chemoenzymatic approach to enantiomerically pure amines using dynamic kinetic resolution: application to the synthesis of norsertraline. Chem. Eur. J., 15, 3403-3410.
83. Hoben, C. E., Kanupp, L., Bäckvall, J.-E. (2008). Practical chemoenzymatic dynamic kinetic resolution of primary amines via transfer of readily removable benzyloxycarbonyl group. Tetrahedron Lett., 49, 977-979.
84. Stenreiber, J., Faber, K., Griengl, H. (2008). De-racemization of enantiomers versus de-epimerization of diastereomers - classifi cation of dynamic kinetic asymmetric transformations (DYKAT). Chem. Eur. J., 14, 8060-8072.
85. Martín-Matute, B., Edin, M., Bäckvall, J.-E. (2006). Highly effi cient synthesis of enantiopure diacetylated C 2-symmetric diols by ruthenium-and enzyme - catalyzed dynamic kinetic asymmetric transformation (DYKAT). Chem. Eur. J., 12, 6053-6061.
86. Leijondahl, K., Borén, L., Braun, R., Bäckvall, J.-E. (2008). Enantiopure 1,5-diols from dynamic kinetic asymmetric transformation. Useful synthetic intermediates for the preparation of chiral heterocycles. Org. Lett., 10, 2027-2030.
87. Leijondahl, K., Borén, L., Braun, R., Bäckvall, J.-E. (2009). Enzyme-and ruthenium-catalyzed dynamic kinetic asymmetric transformation of 1,5-diols. Application to the synthesis of (+)-Solenopsin A. J. Org. Chem., 74, 1988-1993.
88. Holt, J., Hanefeld, U. (2009). Enantioselective enzyme-catalysed synthesis of cyanohydrins. Curr. Org. Synth., 6, 15-37.
89. Andexer, J. N., Langermann, J. V., Kragl, U., Pohl, M. (2009). How to overcome limitations in biotechnology processes - examples from hydroxynitrile lyase applications. Trends Biotechnol., 27, 599-607.
90. Bhunya, R., Mahapatra, T., Nanda, S. (2009). Prunus armeniaca hydroxynitrile lyase (ParsHNL)-catalyzed asymmetric transformation of cyanohydrins from sterically demanding aromatic aldehydes. Tetrahedron: Asymmetry, 20, 1526-1530.
91. van Pelt, S., van Rantwijk, F., Sheldon, R. (2009). Synthesis of aliphatic (S)-a - hydroxycarboxylic amides using a one-pot bienzymatic cascade immobilised oxynitrilase and nitrile hydratase. Adv. Synth. Catal., 351, 397-404.
92. Avi, M., Gaisberger, R., Feichtenhofer, S., Griengl, H. (2009). De novo synthesis of pentoses via cyanohydrins as key intermediates. Tetrahedron, 65, 5418-5426.
93. Janssen, D. B., MajerićElenkov, M., Hasnaoui, G., Hauer, B., Lutje Spelberg, J. H. (2006). Enantioselective formation and ring-opening of epoxides catalysed by halohydrin dehalogenases. Biochem. Soc. Trans., 34, 291-295.
94. MajerićElenkov, M., Tang, L., Hauer, B., Janssen, D. B. (2006). Sequential kinetic resolution catalyzed by halohydrin dehalogenase. Org. Lett., 8, 4227-4229.
95. MajerićElenkov, M., Hoeffken, H. W., Tang, L., Hauer, B., Janssen, D. B. (2007). Enzyme catalyzed nucleophilic ring opening of epoxides for the preparation of enantiopure tertiary alcohols. Adv. Synth. Catal., 349, 2279-2285.
96. Haak, R. M., Berthiol, F., Jerphagnon, T., Gayet, A. J. A., Tarabiono, C., Postema, C. P., Ritleng, V., Pfeffer, M., Janssen, D. B., Minnaard, A. J., Feringa, B. L., de Vries, J. G. (2008). Dynamic kinetic resolution of racemic ß-haloalcohols: direct access to enantioenriched epoxides. J. Am. Chem. Soc., 130, 13508-13509.
97. Clapes, P., Sprenger, G. A., Joglar, J. (2009). Novel strategies in aldolase-catalyzed synthesis of iminosugars. In: W. D. Fessner, T. Anthonsen Modern Biocatalysis: Stereoselective and Environmentally Friendly Reactions, Wiley - VCH, Weinheim, Germany, pp. 299-312.
98. Clapes, P., Fessner, W. D., Sprenger, G. A., Samland, A. K. (2010). Recent progress in stereoselective synthesis with aldolases. Curr. Opin. Chem. Biol., 14, 154-167.
99. Gutiérrez, M. L., Garrabou, X., Agosta, E., Servi, S., Parella, T., Joglar, J., Clapés, P. (2008). Serine hydromethyl transferase from Streptococcus thermophilu s and L-threonine aldolase from Escherichia coli as stereocomplementary biocatalysts for the synthesis of ß-hydroxy-a, ?-amino acids derivatives. Chem. Eur. J., 14, 4647-4656.
100. Fesko, K., Uhl, M., Stenreiber, J., Gruber, K., Griengl, H. (2010). Biocatalytic access to a, a-dialkyl-a-amino acids by a mechanism-based approach. Angew. Chem. Int. Ed., 49, 121-124.
101. Steinreiber, J., Schürmann, M., Wolberg, M., van Assema, F., Reisinger, C., Fesko, K., Mink, D., Griengl, H. (2007). Overcoming thermodynamic and kinetic limitations of aldolase catalyzed reactions by applying multienzymatic dynamic kinetic asymmetric transformations. Angew. Chem. Int. Ed., 46, 1624-1626.
102. Garrabou, X., Castillo, J. A., Guérard-Hélaine, C., Parella, T., Joglar, J., Clapés, P. (2009). Asymmetric self-and cross-aldol reactions of glycoaldehyde catalyzed by D-fructose-6-phosphate aldolase. Angew. Chem. Int. Ed., 48, 5521-5525.
103. Glueck, S. M., Pirker, M., Nestl, B. M., Ueberbacher, B. T., Larissegger-Schnell, B., Csar, K., Hauer, B., Stuermer, R., Kroutil, W., Faber, K. (2005). Biocatalytic racemization of aliphatic, arylaliphatic, and aromatic a-hydroxycarboxylic acids. J. Org. Chem., 70, 4028-4032.
104. Wu, B., Szymanski, W., Wietzes, P., de Wildeman, S., Poelarends, G. J., Feringa, B. L., Janssen, D. B. (2009). Enzymatic synthesis of enantiopure a-and ß-amino acids by phenylalanine aminomutase-catalyzed amination of cinnamic acid derivatives . ChemBioChem, 10, 338-344.
105. Szymanski, W., Wu, B., Weiner, B., de Wildeman, S., Feringa, B. L., Janssen, D. B. (2009). Phenylalanine aminomutase-catalyzed addition of ammonia to substituted cinnamic acids: a route to enantiopure a-and ß-amino acids. J. Org. Chem., 74, 9152-9157.
106. Hansch, H., Leo, A., Taft, R. W. (1971). A survey of Hammett substituent constants and resonance and fi eld parameters. Chem. Rev., 91, 165-195.