Synthesis and biological evaluation of enantiopure thionitrites: The solid-phase synthesis and nitrosation of D-glutathione as a molecular probe

被引：8

作者：

Cavero, M

Hobbs, A

Madge, D

Motherwell, WB

Selwood, D

Potier, P

机构：

[1] UCL, Christopher Ingold Labs, Dept Chem, London WC1H 0AJ, England

[2] Wolfson Inst Biomed Res, London WC1E 6AU, England

[3] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2000年 / 10卷 / 07期

基金：

英国惠康基金;

关键词：

D O I：

10.1016/S0960-894X(00)00060-3

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The D-isomer of the naturally-occurring tripeptide glulathione (gamma-L-Glu-L-Cys-Gly, L-GSH) has been synthesised using the Fmoc solid phase peptide synthesis strategy. The D-GSH obtained has been nitrosated to give the D-isomer of the bioactive thionitrite, S-nitroso-L-glutathione. The biological activity of both enantiomers of S-nitrosoglutathione has been studied and compared to the activity of the D- and L-isomers of N-acetyl-S-nitrosopenicillamine (SNAP) and S-nitrosocysteine (CysNO). (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：641 / 644

页数：4

共 30 条

[1] ALBERT R, 1987, SYNTHESIS-STUTTGART, P635
[2] Butler AR, 1997, ANAL BIOCHEM, V249, P1
[3] THE PHYSIOLOGICAL-ROLE OF NITRIC-OXIDE
BUTLER, AR
WILLIAMS, DLH
[J]. CHEMICAL SOCIETY REVIEWS, 1993, 22 (04) : 233 - 241
[4] AMINO-ACIDS AND PEPTIDES .29. USE OF S-BENZYLTHIOMETHYL-L-CYSTEINE IN PEPTIDE SYNTHESIS - SYNTHESIS OF GLUTATHIONE AND HOMOGLUTATHIONE
CAMBLE, R
PURKAYAS.R
YOUNG, GT
[J]. JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (10): : 1219 - &
[5] FONTECAVE M, 1994, B SOC CHIM FR, V131, P620
[6] Are thiols the carrier of nitric oxide in biological systems? A kinetic model
Gabor, G
Allon, N
Weetall, HH
[J]. MICROCHEMICAL JOURNAL, 1997, 56 (02) : 177 - 187
[7] Cell-mediated biotransformation of S-nitrosoglutathione
Gordge, MP
Addis, P
Noronha-Dutra, AA
Hothersall, JS
[J]. BIOCHEMICAL PHARMACOLOGY, 1998, 55 (05) : 657 - 665
[8] GUTTMAN ST, 1966, HELV CHIM ACTA, V14, P83
[9] GYORGYDEAK Z, 1990, LIEBIGS ANN CHEM, P281
[10] COLOR TEST FOR DETECTION OF FREE TERMINAL AMINO GROUPS IN SOLID-PHASE SYNTHESIS OF PEPTIDES
KAISER, E
COLESCOT.RL
BOSSINGE.CD
COOK, PI
[J]. ANALYTICAL BIOCHEMISTRY, 1970, 34 (02) : 595 - &

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