Unsaturated thioacetic acids as novel mechanism - Based inhibitors of peptidylglycine alpha-hydroxylating monooxygenase

被引：13

作者：

Casara, P ^{[1
]}

Ganzhorn, A ^{[1
]}

Philippo, C ^{[1
]}

Chanal, MC ^{[1
]}

Danzin, C ^{[1
]}

机构：

[1] MARION MERRELL DOW RES INST,STRASBOURG CTR,F-67080 STRASBOURG,FRANCE

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1996年 / 6卷 / 04期

关键词：

D O I：

10.1016/0960-894X(96)00041-8

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Several unsaturated thioacetic acids were synthesized as potential mechanism-based inhibitors of peptidylglycine alpha-hydroxylating monooxygenase (PHM) prepared from horse serum. Trans-styrylthioacetic acid produced potent time-dependent inhibition of PHM. Potential mechanisms are proposed to explain PHM inactivation by unsaturated thioacetic acids.

引用

页码：393 / 396

页数：4

共 21 条

[1] ELIMINATION AND ADDITION-REACTIONS .26. ASYMMETRIC INDUCTION IN ADDITIONS OF NUCLEOPHILES AND ELECTROPHILES TO ALPHA,BETA-UNSATURATED SULFOXIDES [J].

ABBOTT, DJ ;

COLONNA, S ;

STIRLING, CJM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (05) :492-498

[2] RESONANCE STABILIZATION OF HETEROALLYLIC RADICALS [J].

BORDWELL, FG ;

JI, GZ ;

ZHANG, XM .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (18) :5254-5256

[3] 4-PHENYL-3-BUTENOIC ACID, AN INVIVO INHIBITOR OF PEPTIDYLGLYCINE HYDROXYLASE (PEPTIDE AMIDATING ENZYME) [J].

BRADBURY, AF ;

MISTRY, J ;

ROOS, BA ;

SMYTH, DG .

EUROPEAN JOURNAL OF BIOCHEMISTRY, 1990, 189 (02) :363-368

[4] THE BIOSYNTHESIS OF NEUROPEPTIDES - PEPTIDE ALPHA-AMIDATION [J].

EIPPER, BA ;

STOFFERS, DA ;

MAINS, RE .

ANNUAL REVIEW OF NEUROSCIENCE, 1992, 15 :57-85

[5] INHIBITION OF PEPTIDYLGLYCINE ALPHA-AMIDATING MONOOXYGENASE BY N-SUBSTITUTED HOMOCYSTEINE ANALOGS [J].

ERION, MD ;

TAN, J ;

WONG, M ;

JENG, AY .

JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (26) :4430-4437

[6]

KATAPODIS AG, 1990, BIOCHEMISTRY-US, V29, P4541

[7]

KATAPODIS AG, 1990, BIOCHEMISTRY-US, V29, P6115

[8]

KITZ R, 1962, J BIOL CHEM, V237, P3245

[9] IRREVERSIBLE INHIBITION OF MAMMALIAN AND INSECT PEPTIDYLGLYCINE ALPHA-HYDROXYLATING MONOOXYGENASES (PHMS), PEPTIDE AMIDATING ENZYMES, BY N-FORMYL AMIDES [J].

KLINGE, M ;

CHENG, HM ;

ZABRISKIE, TM ;

VEDERAS, JC .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (11) :1379-1380

[10]

LALEZARI I, 1984, SYNTHESIS-STUTTGART, P660

← 1 2 3 →