Practical synthesis of optically active α,α-disubstituted malonamic acids through asymmetric hydrolysis of malonamide derivatives with Rhodococcus sp CGMCC 0497

被引:42
作者
Wu, ZL [1 ]
Li, ZY [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod, Shanghai 200032, Peoples R China
关键词
D O I
10.1021/jo026691u
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A variety of alpha,alpha-disubstituted malonamides undergo enantioselective hydrolysis with Rhodococcus sp. CGMCC 0497 to give challenging enantiopure alpha,alpha-disubstituted malonamic acids with up to >99% enantiomeric excesses and 98% chemical yields. The enantioselectivity originated from the effects of a highly enantioselective amidase. The products could be converted to valuable (R)or (S)-alpha,alpha-dialkylated amino acids after routine conversions.
引用
收藏
页码:2479 / 2482
页数:4
相关论文
共 35 条
[1]   MICROBIAL DEGREDATION OF NITRILE COMPOUNDS .5. ALIPHATIC NITRILE HYDRATASE FROM ARTHROBACTER SP J-1 PURIFICATION AND CHARACTERIZATION [J].
ASANO, Y ;
FUJISHIRO, K ;
TANI, Y ;
YAMADA, H .
AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1982, 46 (05) :1165-1174
[2]   STEREOSELECTIVE HYDROLYSIS OF NITRILES AND AMIDES UNDER MILD CONDITIONS USING A WHOLE-CELL CATALYST [J].
BEARD, T ;
COHEN, MA ;
PARRATT, JS ;
TURNER, NJ ;
CROSBY, J ;
MOILLIET, J .
TETRAHEDRON-ASYMMETRY, 1993, 4 (06) :1085-1104
[3]   Stereoselective synthesis of quaternary α-amino acids.: Part 1:: Acyclic compounds [J].
Cativiela, C ;
Diaz-de-Villegas, MD .
TETRAHEDRON-ASYMMETRY, 1998, 9 (20) :3517-3599
[4]   NEW APPROACHES TO THE ASYMMETRIC-SYNTHESIS OF ALPHA-METHYLPHENYLALANINE [J].
CATIVIELA, C ;
DIAZDEVILLEGAS, MD ;
GALVEZ, JA .
TETRAHEDRON-ASYMMETRY, 1994, 5 (02) :261-268
[5]   Synthesis of novel α-substituted and α,α-disubstituted amino acids by rearrangement of ammonium ylides generated from metal carbenoids [J].
Clark, JS ;
Middleton, MD .
ORGANIC LETTERS, 2002, 4 (05) :765-768
[6]   REGIOSELECTIVE HYDROLYSIS OF AROMATIC DINITRILES USING A WHOLE-CELL CATALYST [J].
CROSBY, J ;
MOILLIET, J ;
PARRATT, JS ;
TURNER, NJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (13) :1679-1687
[7]   An enzyme library approach to biocatalysis: Development of nitrilases for enantioselective production of carboxylic acid derivatives [J].
DeSantis, G ;
Zhu, ZL ;
Greenberg, WA ;
Wong, KV ;
Chaplin, J ;
Hanson, SR ;
Farwell, B ;
Nicholson, LW ;
Rand, CL ;
Weiner, DP ;
Robertson, DE ;
Burk, MJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (31) :9024-9025
[8]  
FABER K, 2000, BIOTRANSFORMATIONS O, pCH2
[9]  
Glockler R, 1996, CHIMIA, V50, P413
[10]   5-cyanovaleramide production using immobilized Pseudomonas chlororaphis B23 [J].
Hann, EC ;
Eisenberg, A ;
Fager, SK ;
Perkins, NE ;
Gallagher, FG ;
Cooper, SM ;
Gavagan, JE ;
Stieglitz, B ;
Hennessey, SM ;
DiCosimo, R .
BIOORGANIC & MEDICINAL CHEMISTRY, 1999, 7 (10) :2239-2245