Overcoming thermodynamic and kinetic limitations of aldolase-catalyzed reactions by applying multienzymatic dynamic kinetic asymmetric transformations

Angewandte Chemie - International Edition

Volumn 46, Issue 10, 2007, Pages 1624-1626

  Steinreiber, Johannes ^a   Schürmann, Martin ^b   Wolberg, Michael ^c   Van Assema, Friso ^b   Reisinger, Christoph ^a   Fesko, Kateryna ^d   Mink, Daniel ^b   Griengl, Herfried ^a  

^a RESEARCH CENTRE APPLIED BIOCATALYSIS   (Austria)

^b Catalysis and Development   (Netherlands)

^c DSM RESOLVE   (Netherlands)

^d GRAZ UNIVERSITY OF TECHNOLOGY   (Austria)

Author keywords

Aldol reaction; Amino alcohols; Biocatalysis; Lyases; Threonine aldolase

Indexed keywords

CATALYSIS; METHYLATION; PHASE TRANSITIONS; REACTION KINETICS; SYNTHESIS (CHEMICAL); THERMODYNAMICS;

ALDOL REACTION; AMINO ALCOHOLS; LYASES; THREONINE ALDOLASE;

ENZYMES;

ALDEHYDE; AMINO ACID; FRUCTOSE BISPHOSPHATE ALDOLASE; GLYCINE;

ARTICLE; CATALYSIS; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; KINETICS; STEREOISOMERISM; SYNTHESIS; THERMODYNAMICS;

ALDEHYDES; AMINO ACIDS; CATALYSIS; FRUCTOSE-BISPHOSPHATE ALDOLASE; GLYCINE; KINETICS; MODELS, CHEMICAL; MOLECULAR STRUCTURE; STEREOISOMERISM; THERMODYNAMICS;

EID: 34248165875     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200604142     Document Type: Article

References (30)

1. a) M. G. Silvestri, G. Desantis, M. Mitchell, C.-H. Wong, Top. Stereochem. 2003, 23, 267-342;
2. b) W.-D. Fessner in Modern Aldol Reactions (Ed.: R. Mahrwald), VCH, Weinheim, 2004, pp. 201-272.
3. L. J. Whalen, C.-H. Wong, Aldrichimica Acta 2006, 39, 63-71.
4. M. Braun in Modern Aldol Reactions (Ed.: R. Mahrwald), VCH, Weinheim, 2004, pp. 1-62.
5. Review on threonine aldolases: J. Q. Liu, T. Dairi, N. Itoh, M. Kataoka, S. Shimizu, H. Yamada, J. Mol. Catal. B 2000, 10, 107-115.
6. a) F. P. Seebeck, D. Hilvert, J. Am. Chem. Soc. 2003, 125, 10158-10159;
7. b) F. P. Seebeck, A. Guainazzi, C. Amoreira, K. K. Baldridge, D. Hilvert, Angew. Chem. 2006, 118, 6978-6980;
8. Angew. Chem. Int. Ed. 2006, 45, 6824-6826.
9. a) B. T. Lotz, C. M. Gasparski, K. Peterson, M. J. Miller, J. Chem. Soc. Chem. Commun. 1990, 1107-1109;
10. b) V. P. Vassilev, T. Uchiyama, T. Kajimoto, C.-H. Wong, Tetrahedron Lett. 1995, 36, 4081-4084;
11. c) T. Kimura, V. P. Vassilev, G.-J. Shen, C.-H. Wong, J. Am. Chem. Soc. 1997, 119, 11734-11742.
12. J. Steinreiber, K. Fesko, C. Reisinger, M. Schürmann, F. van Assema, M. Wolberg, D. Mink, H. Griengl, Tetrahderon 2007, 63, 918-926.
13. M. Bechthold, S. Makart, M. Heinemann, S. Panke, J. Biotechnol. 2006, 124, 146-162.
14. J. Q. Liu, M. Odani, T. Yasuoka, T. Dairi, N. Itoh, M. Kataoka, S. Shimizu, H. Yamada, Appl. Microbiol. Biotechnol. 2000, 54, 44-51.
15. T. Nikaido, N. Kawada, T. Hamatani, Y. Ueda (Daicel Chemical Industries), WO 9523869, 1995;
16. T. Nikaido, N. Kawada, T. Hamatani, Y. Ueda (Daicel Chemical Industries), US 5731175, 1998;
17. T. Nikaido, N. Kawada, T. Hamatani, Y. Ueda (Daicel Chemical Industries), US 5846792, 1998;
18. T. Nikaido, N. Kawada, T. Hamatani, Y. Ueda (Daicel Chemical Industries), US 5874613, 1999.
19. S. Ito, T. Nikaido, A. Matsuyama (Daicel Chemical Industries), JP 46076, 2001.
20. For reviews about parallel kinetic resolution, see a) J. R. Dehli, V. Gotor, Chem. Soc. Rev. 2002, 31, 365-370;
21. b) E. Vedejs, M. Jure, Angew. Chem. 2005, 117, 4040-4069;
22. Angew. Chem. Int. Ed. 2005, 44, 3974-4001.
23. a) T. Boerresen, N. K. Klausen, L. M. Larsen, H. Soerensen, Biochim. Biophys. Acta 1989, 993, 108-115;
24. b) N. Connil, Y. Le Breton, X. Dousset, Y. Auffray, A. Rince, H. Prevost, Appl. Environ. Microbiol. 2002, 68, 3537-3544.
25. J. Q. Liu, S. Ito, T. Dairi, N. Itoh, S. Shimizu, H. Yamada, Appl. Microbiol. Biotechnol. 1998, 49, 702-708.
26. DYKAT: a) asymmetric allyllic alkylation: B. M. Trost, Chem. Pharm. Bull. 2002, 50, 1-14, and references therein;
27. b) chemoenzymatic desymmetrization of 1,3-diols: M. Edin, J. Steinreiber, J.-E. Bäckvall, Proc. Natl. Acad. Sci. USA 2004, 101, 5761-5766.
28. Organocatalytic DYKAT: E. Reyes, A. Cordova, Tetrahedron Lett. 2005, 46, 6605-6609.
29. a) O. Pamies, J.-E. Baeckvall, Chem. Rev. 2003, 103, 3247-3261;
30. b) H. Pellissier, Tetrahedron 2003, 59, 8291-8327.