Synthesis of (2S,5S)-5-fluoromethylornithine; A potent inhibitor of ornithine aminotransferase

被引：10

作者：

Ducep, JB

Heintzelmann, B

Jund, K

Lesur, B

Schleimer, M

Zimmermann, PR

机构：

[1] Marion Merrell Research Institute, Strasbourg Research Center, 67080 Strasbourg

来源：

TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 02期

关键词：

D O I：

10.1016/S0957-4166(96)00504-6

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Only one of the four enantiomers of 5-fluoromethylomithine 1 was an irreversible inhibitor of ornithine aminotransferase. The active enantiomer la was synthesized from diaminoadipic acid 2 with a chemical diastereomeric separation and an enantiomeric resolution by hydrolysis of a phenylacetamide with benzylpenicillinase. (C) 1997 Elsevier Science Ltd.

引用

收藏

页码：327 / 335

页数：9

相关论文

共 17 条

[1] DL-CANALINE AND 5-FLUOROMETHYLORNITHINE - COMPARISON OF 2 INACTIVATORS OF ORNITHINE AMINOTRANSFERASE [J].

BOLKENIUS, FN ;

KNODGEN, B ;

SEILER, N .

BIOCHEMICAL JOURNAL, 1990, 268 (02) :409-414

[2] NEW POWERFUL CATALYSTS FOR THE REDUCTION OF ESTERS BY LITHIUM BOROHYDRIDE [J].

BROWN, HC ;

NARASIMHAN, S .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (08) :1604-1606

[3]

DUANE G, 1988, BIOCHEM J, V253, P481

[4]

Ducep JB, 1996, ACS SYM SER, V639, P196

[5]

FISMAN M, 1985, AM J PSYCHIAT, V142, P71

[6] AMMONIA IS ENDOGENOUSLY GENERATED IN THE BRAIN IN THE PRESENCE OF PRESUMED AND VERIFIED DEMENTIA OF ALZHEIMER TYPE [J].

HOYER, S ;

NITSCH, R ;

OESTERREICH, K .

NEUROSCIENCE LETTERS, 1990, 117 (03) :358-362

[7] AMINO-ACID DERIVATIVES THAT STABILIZE SECONDARY STRUCTURES OF POLYPEPTIDES .1. SYNTHESIS OF LL-3-AMINO-2-PIPERIDONE-6-CARBOXYLIC ACID (LL-ACP), A NOVEL BETA-TURN-FORMING AMINO-ACID [J].

KEMP, DS ;

SUN, ET .

TETRAHEDRON LETTERS, 1982, 23 (37) :3759-3760

[8]

LI JP, 1989, INT J PEPT PROT RES, V34, P311

[9] SYNTHESIS OF OPTICALLY PURE MECHANISM-BASED INHIBITORS OF GAMMA-AMINOBUTYRIC-ACID AMINOTRANSFERASE (GABA-T) VIA ENZYME-CATALYZED RESOLUTION [J].

MARGOLIN, AL .

TETRAHEDRON LETTERS, 1993, 34 (08) :1239-1242

[10] EFFECTS OF INHIBITION OF ORNITHINE AMINOTRANSFERASE ON THIOACETAMIDE-INDUCED HEPATOGENIC ENCEPHALOPATHY [J].

SARHAN, S ;

KNODGEN, B ;

GRAUFFEL, C ;

SEILER, N .

NEUROCHEMICAL RESEARCH, 1993, 18 (04) :539-549