ENZYMATIC RESOLUTION OF AMPA BY USE OF ALPHA-CHYMOTRYPSIN

被引:14
作者
NIELSEN, B
FISKER, H
EBERT, B
MADSEN, U
CURTIS, DR
KROGSGAARDLARSEN, P
HANSEN, JJ
机构
[1] ROYAL DANISH SCH PHARM,DEPT ORGAN CHEM,PHARMABIOTEC RES CTR,DK-2100 COPENHAGEN,DENMARK
[2] AUSTRALIAN NATL UNIV,JOHN CURTIN SCH MED RES,CANBERRA,ACT 2601,AUSTRALIA
关键词
D O I
10.1016/S0960-894X(00)80102-X
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
The enantiomers of AMPA and its diethyl derivative were prepared by an enzymatic resolution using alpha-chymotrypsin in solution. Electrophysiological studies in vivo and in vitro showed the excitatory effects of AMPA to reside mainly in the L-enantiomer in agreement with the IC50 values of 0.02 muM and 76 muM observed for the L- and D-enantiomer, respectively, in [H-3]AMPA binding assays.
引用
收藏
页码:107 / 114
页数:8
相关论文
共 19 条
[1]   KINETIC RESOLUTION OF UNNATURAL AND RARELY OCCURRING AMINO-ACIDS - ENANTIOSELECTIVE HYDROLYSIS OF N-ACYL AMINO-ACIDS CATALYZED BY ACYLASE-I [J].
CHENAULT, HK ;
DAHMER, J ;
WHITESIDES, GM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (16) :6354-6364
[2]  
COHEN SG, 1969, J BIOL CHEM, V244, P2664
[3]  
GREENSTEIN JP, 1961, CHEM AMINO ACIDS, P1753
[4]  
GREENSTEIN JP, 1961, CHEM AMINO ACIDS, P737
[5]   SEPARATION OF THE OPTICAL ISOMERS OF AMINO-ACIDS BY LIGAND-EXCHANGE CHROMATOGRAPHY USING CHEMICALLY BONDED CHIRAL PHASES [J].
GUBITZ, G ;
JELLENZ, W ;
SANTI, W .
JOURNAL OF CHROMATOGRAPHY, 1981, 203 (JAN) :377-384
[6]   ISOXAZOLE AMINO-ACIDS AS GLUTAMIC-ACID AGONISTS - SYNTHESIS OF SOME ANALOGS AND HOMOLOGS OF IBOTENIC ACID [J].
HANSEN, JJ ;
KROGSGAARDLARSEN, P .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (08) :1826-1833
[7]   STRUCTURAL, CONFORMATIONAL, AND STEREOCHEMICAL REQUIREMENTS OF CENTRAL EXCITATORY AMINO-ACID RECEPTORS [J].
HANSEN, JJ ;
KROGSGAARDLARSEN, P .
MEDICINAL RESEARCH REVIEWS, 1990, 10 (01) :55-94
[8]   EXCITATORY AMINO-ACID AGONISTS - ENZYMIC RESOLUTION, X-RAY STRUCTURE, AND ENANTIOSELECTIVE ACTIVITIES OF (R)-BROMOHOMOIBOTENIC AND (S)-BROMOHOMOIBOTENIC ACID [J].
HANSEN, JJ ;
NIELSEN, B ;
KROGSGAARDLARSEN, P ;
BREHM, L ;
NIELSEN, EO ;
CURTIS, DR .
JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (10) :2254-2260
[9]   ENZYMIC RESOLUTION AND BINDING TO RAT-BRAIN MEMBRANES OF THE GLUTAMIC-ACID AGONIST ALPHA-AMINO-3-HYDROXY-5-METHYL-4-ISOXAZOLEPROPIONIC ACID [J].
HANSEN, JJ ;
LAURIDSEN, J ;
NIELSEN, E ;
KROGSGAARDLARSEN, P .
JOURNAL OF MEDICINAL CHEMISTRY, 1983, 26 (06) :901-903
[10]   QUANTITATIVE STUDIES ON SOME ANTAGONISTS OF N-METHYL D-ASPARTATE IN SLICES OF RAT CEREBRAL-CORTEX [J].
HARRISON, NL ;
SIMMONDS, MA .
BRITISH JOURNAL OF PHARMACOLOGY, 1985, 84 (02) :381-391