Enantioselective transaminations by dendrimeric enzyme mimics

作者: Ronald Breslow , Sujun Wei , Craig Kenesky

DOI: 10.1016/J.TET.2007.02.052

关键词: Organic chemistryAlanineDendrimerStereochemistryFolding (chemistry)PhenylalanineEnantioselective synthesisChemistryPyridoxamineTransaminationEnzyme

摘要: PAMAM dendrimers have been constructed with a pyridoxamine core and chiral capping amino groups. Transamination to form phenylalanine alanine from their related keto acids produced enantioselectivities induced by the formally remote caps, supporting computer models that indicate folding of dendrimer chains back into region.

参考文章(25)
Lei Liu, Mary Rozenman, Ronald Breslow, Hydrophobic effects on rates and substrate selectivities in polymeric transaminase mimics. Journal of the American Chemical Society. ,vol. 124, pp. 12660- 12661 ,(2002) , 10.1021/JA028151K
Lei Liu, Ronald Breslow, Selective racemization in preference to transamination catalyzed by pyridoxal enzyme analogs Tetrahedron Letters. ,vol. 42, pp. 2775- 2777 ,(2001) , 10.1016/S0040-4039(01)00329-X
Ronald Breslow, Milton Hammond, Manfred Lauer, Selective transamination and optical induction by a .beta.-cyclodextrin-pyridoxamine artificial enzyme Journal of the American Chemical Society. ,vol. 102, pp. 421- 422 ,(1980) , 10.1021/JA00521A093
Wenjun Zhou, Lei Liu, Ronald Breslow, Transamination by polymeric enzyme mimics Helvetica Chimica Acta. ,vol. 86, pp. 3560- 3567 ,(2003) , 10.1002/HLCA.200390300
Steven C. Zimmerman, Anthony W. Czarnik, Ronald Breslow, Intramolecular general base-acid catalysis in transaminations catalyzed by pyridoxamine enzyme analogs Journal of the American Chemical Society. ,vol. 105, pp. 1694- 1695 ,(1983) , 10.1021/JA00344A069
Ronald Breslow, Jean Chmielewski, Diane Foley, Bruce Johnson, Naofumi Kumabe, Michael Varney, Raj Mehra, Optically Active Amino Acid Synthesis by Artificial Transaminase Enzymes Tetrahedron. ,vol. 44, pp. 5515- 5524 ,(1988) , 10.1016/S0040-4020(01)86057-9
Jeffrey Winkler, Evdoxia Coutouli-Argyropoulou, Reinhard Leppkes, Ronald Breslow, Artificial transaminase carrying a synthetic macrocyclic binding group Journal of the American Chemical Society. ,vol. 105, pp. 7198- 7199 ,(1983) , 10.1021/JA00362A045
D A Tomalia, H Baker, J Dewald, M Hall, G Kallos, S Martin, J Roeck, J Ryder, P Smith, A New Class of Polymers: Starburst-Dendritic Macromolecules Polymer Journal. ,vol. 17, pp. 117- 132 ,(1985) , 10.1295/POLYMJ.17.117
Lei Liu, Ronald Breslow, A Potent Polymer/Pyridoxamine Enzyme Mimic Journal of the American Chemical Society. ,vol. 124, pp. 4978- 4979 ,(2002) , 10.1021/JA025895P