Asymmetric bioreductions of β-nitro acrylates as a route to chiral β2-Amino acids

被引:82
作者
Swiderska, Magdalena A. [1 ]
Stewart, Jon D. [1 ]
机构
[1] Univ Florida, Dept Chem, Gainesville, FL 32611 USA
关键词
D O I
10.1021/ol062612f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reductions of beta-nitroacrylates by Saccharomyces carlsbergensis old yellow enzyme is the key step in a concise route to optically active beta(2)-amino acids. The enzymatic reductions occur with 87 - 96% ee, with larger substrates providing greater stereoselectivities. This work extends enantioselective enzymatic alkene reductions to include acyclic systems with weakly coordinating substituents.
引用
收藏
页码:6131 / 6133
页数:3
相关论文
共 35 条
[1]  
ABRAMOVITZ AS, 1976, J BIOL CHEM, V251, P5321
[2]   Nitroalkanes and ethyl glyoxalate as common precursors for the preparation of both β-keto esters and α,β-unsaturated esters [J].
Ballini, R ;
Fiorini, D ;
Palmieri, A .
TETRAHEDRON LETTERS, 2004, 45 (38) :7027-7029
[3]   The role of glutamine 114 in Old Yellow Enzyme [J].
Brown, BJ ;
Hyun, JW ;
Duvvuri, S ;
Karplus, PA ;
Massey, V .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2002, 277 (03) :2138-2145
[4]   Asymmetric synthesis of beta-amino acids and alpha-substituted beta-amino acids [J].
Cardillo, G ;
Tomasini, C .
CHEMICAL SOCIETY REVIEWS, 1996, 25 (02) :117-&
[5]   Asymmetric Henry reaction catalyzed by C2-symmetric tridentate bis(oxazoline) and bis(thiazoline) complexes:: Metal-controlled reversal of enantioselectivity [J].
Du, DM ;
Lu, SF ;
Fang, T ;
Xu, JX .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (09) :3712-3715
[6]   Stereoselective synthesis of β2-amino acids by Michael addition of diorgano zinc reagents to nitro acrylates [J].
Eilitz, U ;
Lessmann, F ;
Seidelmann, O ;
Wendisch, V .
TETRAHEDRON-ASYMMETRY, 2003, 14 (02) :189-191
[7]   Stereoselective Michael addition of trimethyl aluminium to nitro acrylates: a route to 2-methyl-3-amino propionic acid [J].
Eilitz, U ;
Lessmann, F ;
Seidelmann, O ;
Wendisch, V .
TETRAHEDRON-ASYMMETRY, 2003, 14 (20) :3095-3097
[8]   An enantioselective synthesis of β2-amino acid derivatives [J].
Elaridi, J ;
Thaqi, A ;
Prosser, A ;
Jackson, WR ;
Robinson, AJ .
TETRAHEDRON-ASYMMETRY, 2005, 16 (07) :1309-1319
[9]   OLD YELLOW ENZYME AT 2-ANGSTROM RESOLUTION - OVERALL STRUCTURE, LIGAND-BINDING, AND COMPARISON WITH RELATED FLAVOPROTEINS [J].
FOX, KM ;
KARPLUS, PA .
STRUCTURE, 1994, 2 (11) :1089-1105
[10]  
GANGADHAR N, 2000, ORG LETT, V2, P3527