Synthesis of dipeptide-bound epoxides and α,β-unsaturated amides as potential irreversible transglutaminase inhibitors

被引：41

作者：

de Macédo, P ^{[1
]}

Marrano, C ^{[1
]}

Keillor, JW ^{[1
]}

机构：

[1] Univ Montreal, Dept Chim, Montreal, PQ H3C 3J7, Canada

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2002年 / 10卷 / 02期

基金：

加拿大自然科学与工程研究理事会;

关键词：

D O I：

10.1016/S0968-0896(01)00292-9

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 [生物化学与分子生物学]; 081704 [应用化学];

摘要：

Herein we report the synthesis of 24 novel peptides Lis potential irreversible inactivators of transglutaminase (TGase). These peptides were designed to resemble Cbz-L-Gln-Gly, known to be a good TGase substrate, and to include either alpha,beta -unsaturated amide groups or the corresponding epoxide groups. The side chain length: of the amino acid residue bearing the inhibitor group was also varied in order to permit investigation of this effect. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：355 / 360

页数：6

共 47 条

[1]

DIOXIRANE EPOXIDATION OF ALPHA,BETA-UNSATURATED KETONES [J].

ADAM, W ;

HADJIARAPOGLOU, L ;

SMERZ, A .

CHEMISCHE BERICHTE, 1991, 124 (01) :227-232

[2]

A CONVENIENT PREPARATION OF ACETONE SOLUTIONS OF DIMETHYLDIOXIRANE [J].

ADAM, W ;

BIALAS, J ;

HADJIARAPOGLOU, L .

CHEMISCHE BERICHTE, 1991, 124 (10) :2377-2377

[3]

HIV-1 GP120-DEPENDENT INDUCTION OF APOPTOSIS IN ANTIGEN-SPECIFIC HUMAN T-CELL CLONES IS CHARACTERIZED BY TISSUE TRANSGLUTAMINASE EXPRESSION AND PREVENTED BY CYCLOSPORINE-A [J].

AMENDOLA, A ;

LOMBARDI, G ;

OLIVERIO, S ;

COLIZZI, V ;

PIACENTINI, M .

FEBS LETTERS, 1994, 339 (03) :258-264

[4]

SOLID-STATE C-13 NMR-STUDY OF A TRANSGLUTAMINASE INHIBITOR ADDUCT [J].

AUGER, M ;

MCDERMOTT, AE ;

ROBINSON, V ;

CASTELHANO, AL ;

BILLEDEAU, RJ ;

PLIURA, DH ;

KRANTZ, A ;

GRIFFIN, RG .

BIOCHEMISTRY, 1993, 32 (15) :3930-3934

[5]

AZARI P, 1981, CURR EYE RES, P463

[6]

Propagating structure of Alzheimer's β-amyloid(10-35) is parallel β-sheet with residues in exact register [J].

Benzinger, TLS ;

Gregory, DM ;

Burkoth, TS ;

Miller-Auer, H ;

Lynn, DG ;

Botto, RE ;

Meredith, SC .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1998, 95 (23) :13407-13412

[7]

PRECOCIOUS APPEARANCE OF INVOLUCRIN AND EPIDERMAL TRANSGLUTAMINASE DURING DIFFERENTIATION OF PSORIATIC SKIN [J].

BERNARD, BA ;

REANO, A ;

DARMON, YM ;

THIVOLET, J .

BRITISH JOURNAL OF DERMATOLOGY, 1986, 114 (03) :279-283

[8]

ENHANCED TRANSGLUTAMINASE ACTIVITY IN TRANSFORMED HUMAN-LUNG FIBROBLAST CELLS AFTER EXPOSURE TO SODIUM-BUTYRATE [J].

BIRCKBICHLER, PJ ;

ORR, GR ;

PATTERSON, MK ;

CONWAY, E ;

CARTER, HA ;

MAXWELL, MD .

BIOCHIMICA ET BIOPHYSICA ACTA, 1983, 763 (01) :27-34

[9]

A highly conserved lysine residue on the head domain of type II keratins is essential for the attachment of keratin intermediate filaments to the cornified cell envelope through isopeptide crosslinking by transglutaminases [J].

Candi, E ;

Tarcsa, E ;

Digiovanna, JJ ;

Compton, JG ;

Elias, PM ;

Marekov, LN ;

Steinert, PM .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1998, 95 (05) :2067-2072

[10]

SYNTHESIS, CHEMISTRY, AND ABSOLUTE-CONFIGURATION OF NOVEL TRANSGLUTAMINASE INHIBITORS CONTAINING A 3-HALO-4,5-DIHYDROISOXAZOLE [J].

CASTELHANO, AL ;

BILLEDEAU, R ;

PLIURA, DH ;

BONAVENTURA, BJ ;

KRANTZ, A .

BIOORGANIC CHEMISTRY, 1988, 16 (03) :335-340

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