ASYMMETRIC-SYNTHESIS OF (S)-4-AMINOHEX-5-ENOIC ACID - A POTENT INHIBITOR OF 4-AMINOBUTYRATE-2-OXOGLUTARATE AMINOTRANSFERASE

被引：46

作者：

KWON, TW ^{[1
]}

KEUSENKOTHEN, PF ^{[1
]}

SMITH, MB ^{[1
]}

机构：

[1] UNIV CONNECTICUT,DEPT CHEM,ROOM 151,215 GLENBROOK RD,STORRS,CT 06269

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 23期

关键词：

D O I：

10.1021/jo00049a023

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The potent inhibitor of 4-aminobutyrate-2-oxoglutarate aminotransferase (GABA-T), 4-aminohex-5-enoic acid (vinyl GABA), has been synthesized with excellent enantioselectivity in six steps from L-glutamic acid in an overall yield of 33%. This is the most efficient synthesis of this important compound and illustrates the use of a novel alkenyl protecting group for pyroglutamate. This allowed the preparation and manipulation of the key (S)-2-oxopyrrolidine-5-carboxaldehyde intermediate.

引用

页码：6169 / 6173

页数：5

共 37 条

[1] THE HYDROGENATION OF ESTERS TO ALCOHOLS AT 25-DEGREES-150-DEGREES [J].

ADKINS, H ;

BILLICA, HR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1948, 70 (09) :3121-3125

[2] ANTAGONISM OF A KAINIC ACID SYNDROME BY BACLOFEN AND OTHER PUTATIVE GABAMIMETICS [J].

BERNARD, PS ;

SOBISKI, RE ;

DAWSON, KM .

BRAIN RESEARCH BULLETIN, 1980, 5 :519-523

[3]

Bodor N., 1983, PHARMACOL THERAPEUT, V19, P337

[4]

BODOR N, 1982, OPTIMIZATION DRUG DE, P156

[5] BICUCULLINE, AN ANTAGONIST OF GABA AND SYNAPTIC INHIBITION IN SPINAL CORD OF CAT [J].

CURTIS, DR ;

DUGGAN, AW ;

FELIX, D ;

JOHNSTON, GA .

BRAIN RESEARCH, 1971, 32 (01) :69-&

[6]

CURTIS DR, 1981, EXP BRAIN RES, V42, P158

[7] ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].

DALE, JA ;

DULL, DL ;

MOSHER, HS .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&

[8] ACTION OF BETA-PHENYL-GABA DERIVATIVES ON NEURONS OF CAT CEREBRAL-CORTEX [J].

DAVIES, J ;

WATKINS, JC .

BRAIN RESEARCH, 1974, 70 (03) :501-505

[9]

Enna SJ, 1983, GABA RECEPTORS

[10]

Grieben W., Br. UK Pat. Appl., Patent No. [GB 2,133,002, 2133002]

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