ALPHA-CHYMOTRYPSIN CATALYZED ENANTIOSELECTIVE HYDROLYSIS OF ALKENYL-ALPHA-AMINO ACID-ESTERS

被引:16
作者
SCHRICKER, B
THIRRING, K
BERNER, H
机构
[1] Sandoz Forschungsinstitut, A-1235 Wien
关键词
D O I
10.1016/S0960-894X(00)80152-3
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Preparative scale hydrolyses (0.1-0.3 M) were carried out on a series of alkenyl-alpha-aminoacid esters catalyzed by different hydrolytic enzymes. Within the scope of investigated substrates (1-10) and enzymes (PLE, chymopapain, papain, chymotrypsin, trypsin) alpha-chymotrypsin was shown to be the most effective. It showed broad substrate specificity, high stereoselectivity (ee 86-96%) and gave high chemical yields (up to 99%).
引用
收藏
页码:387 / 390
页数:4
相关论文
共 19 条
[1]   A REINVESTIGATION OF MIXED CARBONIC ANHYDRIDE METHOD OF PEPTIDE SYNTHESIS [J].
ANDERSON, GW ;
ZIMMERMAN, JE ;
CALLAHAN, FM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (19) :5012-+
[2]  
BERNER H, UNPUB
[3]   SYNTHESIS OF RP-56142 - A NEW IMMUNOACTIVE PEPTIDE [J].
BOUCHAUDON, J ;
DUTRUCROSSET, G ;
FARGE, D ;
JAMES, C .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (04) :695-701
[4]   AUTOMATED ENANTIOSEPARATION OF AMINO-ACIDS BY DERIVATIZATION WITH ORTHO-PHTHALDIALDEHYDE AND N-ACYLATED CYSTEINES [J].
BRUCKNER, H ;
WITTNER, R ;
GODEL, H .
JOURNAL OF CHROMATOGRAPHY, 1989, 476 :73-82
[5]   CHIRALLY SELECTIVE HYDROLYSIS OF D,L-AMINO ACID-ESTERS BY ALKALINE PROTEASE [J].
CHEN, ST ;
WANG, KT ;
WONG, CH .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (20) :1514-1516
[6]   CHEMOENZYMIC SYNTHESIS OF CHIRAL FURAN-DERIVATIVES - USEFUL BUILDING-BLOCKS FOR OPTICALLY-ACTIVE STRUCTURES [J].
DRUECKHAMMER, DG ;
BARBAS, CF ;
NOZAKI, K ;
WONG, CH ;
WOOD, CY ;
CIUFOLINI, MA .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (08) :1607-1611
[7]   ASYMMETRIC-SYNTHESIS OF ALPHA-ALKYLATED ALPHA-AMINO-ACIDS VIA SCHMIDT REARRANGEMENT OF ALPHA,ALPHA-BISALKYLATED BETA-KETO-ESTERS [J].
GEORG, GI ;
GUAN, XM ;
KANT, J .
TETRAHEDRON LETTERS, 1988, 29 (04) :403-406
[8]  
HORIKAWA H, 1976, TETRAHEDRON LETT, P191
[9]  
KOBER R, 1982, ANGEW CHEM, V94, P213
[10]   ENZYMATIC KINETIC RESOLUTION OF ALPHA-NITRO ALPHA-METHYL CARBOXYLIC-ACIDS [J].
LALONDE, JJ ;
BERGBREITER, DE ;
WONG, CH .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (10) :2323-2327