Microbial aldolases as C–C bonding enzymes—unknown treasures and new developments

作者: Anne K. Samland , Georg A. Sprenger

DOI: 10.1007/S00253-006-0422-6

关键词:

摘要: Aldolases are a specific group of lyases that catalyze the reversible stereoselective addition donor compound (nucleophile) onto an acceptor (electrophile). Whereas most aldolases for their in aldolization reaction, they often tolerate wide range aldehydes as compounds. C–C bonding by creates stereocenters resulting aldol products. This makes interesting tools asymmetric syntheses rare sugars or sugar-derived compounds iminocyclitols, statins, epothilones, and sialic acids. Besides well-known fructose 1,6-bisphosphate aldolase, other microbial origin have attracted interest synthetic bio-organic chemists recent years. These either dihydroxyacetone phosphate depending on pyruvate/phosphoenolpyruvate, glycine, acetaldehyde substrate. Recently, aldolase accepts hydroxyacetone was described. A further enlargement arsenal available chemoenzymatic can be achieved through screening novel activities directed evolution existing to alter substrate- stereospecifities. We give update work aldolases, with emphasis aldolases.

参考文章(110)
I A Rose, E L O'Connell, Studies on the Interaction of Aldolase with Substrate Analogues Journal of Biological Chemistry. ,vol. 244, pp. 126- 134 ,(1969) , 10.1016/S0021-9258(19)78201-5
Franz Effenberger, Alexander Straub, Peter Fischer, Aldolase-catalyzed C-C bond formation for stereoselective synthesis of nitrogen-containing carbohydrates Journal of Organic Chemistry. ,vol. 55, pp. 3926- 3932 ,(1990) , 10.18419/OPUS-1124
Wolf-Dieter Fessner, Enzyme mediated CC bond formation Current Opinion in Chemical Biology. ,vol. 2, pp. 85- 97 ,(1998) , 10.1016/S1367-5931(98)80040-9
Dirk Franke, Che-Chang Hsu, Chi-Huey Wong, Directed evolution of aldolases. Methods in Enzymology. ,vol. 388, pp. 224- 238 ,(2004) , 10.1016/S0076-6879(04)88020-0
Kathryn M. Koeller, Chi-Huey Wong, Enzymes for chemical synthesis Nature. ,vol. 409, pp. 232- 240 ,(2001) , 10.1038/35051706
W. A. Greenberg, A. Varvak, S. R. Hanson, K. Wong, H. Huang, P. Chen, M. J. Burk, Development of an efficient, scalable, aldolase-catalyzed process for enantioselective synthesis of statin intermediates Proceedings of the National Academy of Sciences of the United States of America. ,vol. 101, pp. 5788- 5793 ,(2004) , 10.1073/PNAS.0307563101
Eva González-García, Virgil Helaine, Gérard Klein, Melanie Schuermann, Georg A. Sprenger, Wolf-Dieter Fessner, Jean-Louis Reymond, Fluorogenic stereochemical probes for transaldolases. Chemistry: A European Journal. ,vol. 9, pp. 893- 899 ,(2003) , 10.1002/CHEM.200390110
Akio Ozaki, Eric J. Toone, Claus H. Von der Osten, Anthony J. Sinskey, George M. Whitesides, Overproduction and substrate specificity of a bacterial fuculose-1-phosphate aldolase: a new enzymic catalyst for stereocontrolled aldol condensation Journal of the American Chemical Society. ,vol. 112, pp. 4970- 4971 ,(1990) , 10.1021/JA00168A058
Ji-Quan Liu, Tohru Dairi, Nobuya Itoh, Michihiko Kataoka, Sakayu Shimizu, Hideaki Yamada, Diversity of microbial threonine aldolases and their application Journal of Molecular Catalysis B: Enzymatic. ,vol. 10, pp. 107- 115 ,(2000) , 10.1016/S1381-1177(00)00118-1
Dominique Crestia, Colette Demuynck, Jean Bolte, Transketolase and fructose-1,6-bis-phosphate aldolase, complementary tools for access to new ulosonic acid analogues Tetrahedron. ,vol. 60, pp. 2417- 2425 ,(2004) , 10.1016/J.TET.2003.12.069