Biocatalytic Imine Reduction and Reductive Amination of Ketones

被引:180
作者
Schrittwieser, Joerg H. [1 ]
Velikogne, Stefan [1 ]
Kroutil, Wolfgang [1 ]
机构
[1] Graz Univ, Dept Chem Organ & Bioorgan Chem, NAWI Graz, A-8010 Graz, Austria
关键词
amines; biocatalysis; imines; reduction; reductive amination; AMINO-ACID DEHYDROGENASE; L-PIPECOLIC ACID; SUBSTITUTED ASPARTIC ACIDS; ARTIFICIAL METALLOENZYMES; ASYMMETRIC-SYNTHESIS; ENZYMATIC-SYNTHESIS; CRYSTAL-STRUCTURE; ESCHERICHIA-COLI; PYRROLINE-5-CARBOXYLATE REDUCTASE; ENANTIOSELECTIVE SYNTHESIS;
D O I
10.1002/adsc.201500213
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Chiral amines represent a prominent functional group in pharmaceuticals and agrochemicals and are hence attractive targets for asymmetric synthesis. Since the pharmaceutical industry has identified biocatalysis as a valuable tool for synthesising chiral molecules with high enantiomeric excess and under mild reaction conditions, enzymatic methods for chiral amine synthesis are increasing in importance. Among the strategies available in this context, the asymmetric reduction of imines by NAD(P)H-dependent enzymes and the related reductive amination of ketones have long remained underrepresented. However, recent years have witnessed an impressive progress in the application of natural or engineered imine-reducing enzymes, such as imine reductases, opine dehydrogenases, amine dehydrogenases, and artificial metalloenzymes. This review provides a comprehensive overview of biocatalytic imine reduction and reductive amination of ketones, highlighting the natural roles, substrate scopes, structural features, and potential application fields of the involved enzymes.
引用
收藏
页码:1655 / 1685
页数:31
相关论文
共 200 条
[41]   ENZYMATIC FORMATION OF (R)-RETICULINE FROM 1,2-DEHYDRORETICULINE IN THE OPIUM POPPY PLANT [J].
DEEKNAMKUL, W ;
ZENK, MH .
TETRAHEDRON LETTERS, 1990, 31 (34) :4855-4858
[42]  
DEEKNAMKUL W, 1992, PHYTOCHEMISTRY, V31, P813, DOI 10.1016/0031-9422(92)80020-F
[43]   NADP-glutamate dehydrogenase isoenzymes of Saccharomyces cerevisiae -: Purification, kinetic properties, and physiological roles [J].
DeLuna, A ;
Avendaño, A ;
Riego, L ;
González, A .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2001, 276 (47) :43775-43783
[44]   Artificial Transfer Hydrogenases for the Enantioselective Reduction of Cyclic Imines [J].
Duerrenberger, Marc ;
Heinisch, Tillmann ;
Wilson, Yvonne M. ;
Rossel, Thibaud ;
Nogueira, Elisa ;
Knoerr, Livia ;
Mutschler, Annette ;
Kersten, Karoline ;
Zimbron, Malcolm Jeremy ;
Pierron, Julien ;
Schirmer, Tilman ;
Ward, Thomas R. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (13) :3026-3029
[45]  
Durrenberger M., 2011, ANGEW CHEMIE, V123, P3082
[46]   Bioreduction of β-carboline imines to amines employing Saccharomyces bayanus [J].
Espinoza-Moraga, Marlene ;
Petta, Tania ;
Vasquez-Vasquez, Marco ;
Felipe Laurie, V. ;
Moraes, Luis A. B. ;
Silva Santos, Leonardo .
TETRAHEDRON-ASYMMETRY, 2010, 21 (16) :1988-1992
[47]   Critical residues for structure and catalysis in short-chain dehydrogenases/reductases [J].
Filling, C ;
Berndt, KD ;
Benach, J ;
Knapp, S ;
Prozorovski, T ;
Nordling, E ;
Ladenstein, R ;
Jörnvall, H ;
Oppermann, U .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2002, 277 (28) :25677-25684
[48]   Enantiomeric Natural Products: Occurrence and Biogenesis [J].
Finefield, Jennifer M. ;
Sherman, David H. ;
Kreitman, Martin ;
Williams, Robert M. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (20) :4802-4836
[49]   Biosynthesis of nonribosomal peptides [J].
Finking, R ;
Marahiel, MA .
ANNUAL REVIEW OF MICROBIOLOGY, 2004, 58 :453-488
[50]   ISOLATION AND CHARACTERIZATION OF DIHYDROPTERIDINE REDUCTASE FROM HUMAN-LIVER [J].
FIRGAIRA, FA ;
COTTON, RGH ;
DANKS, DM .
BIOCHEMICAL JOURNAL, 1981, 197 (01) :31-43