Observations on the reactivity of thiyl radicals derived from 3,6-epidithiodiketopiperazine-2,5-diones and related congeners

被引：16

作者：

Hilton, ST

Motherwell, WB

Potier, P

Pradet, C

Selwood, DL

机构：

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

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

[3] UCL, Wolfson Inst Biomed Res, London WC1E 6BT, England

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2005年 / 15卷 / 09期

基金：

英国生物技术与生命科学研究理事会;

关键词：

D O I：

10.1016/j.bmcl.2005.03.022

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A range of thiyl radicals derived from the reduced form of epidithiodiketopiperazines (ETPs) act as polarity reversal catalysts for the hydrosilylation of an enol lactone but not for H-atom abstraction from a model ribose ester. (c) 2005 Elsevier Ltd. All rights reserved.

引用

收藏

页码：2239 / 2242

页数：4

相关论文

共 25 条

[1] THE REVERSE OF THE REPAIR REACTION OF THIOLS - H-ABSTRACTION AT CARBON BY THIYL RADICALS [J].

AKHLAQ, MS ;

SCHUCHMANN, HP ;

VONSONNTAG, C .

INTERNATIONAL JOURNAL OF RADIATION BIOLOGY, 1987, 51 (01) :91-102

[2] A novel redox mechanism for the glutathione-dependent reversible uptake of a fungal toxin in cells [J].

Bernardo, PH ;

Brasch, N ;

Chai, CLL ;

Waring, P .

JOURNAL OF BIOLOGICAL CHEMISTRY, 2003, 278 (47) :46549-46555

[3] Evidence for gliotoxin-glutathione conjugate adducts [J].

Bernardo, PH ;

Chai, CLL ;

Deeble, GJ ;

Liu, XM ;

Waring, P .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (04) :483-485

[4] Carbohydrate-derived thiols as protic polarity-reversal catalysts for enantioselective radical-chain reactions [J].

Cai, YD ;

Roberts, BP ;

Tocher, DA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (11) :1376-1386

[5] Radical-chain racemisation of tetrahydrofurfuryl acetate under conditions of polarity-reversal catalysis: possible implications for the radical-induced strand cleavage of DNA [J].

Cai, YD ;

Roberts, BP .

CHEMICAL COMMUNICATIONS, 1998, (10) :1145-1146

[6] The first electrochemical study of epidithiopiperazine-2,5-diones, a special class of α,α′-disulfide bridged cyclic dipeptides [J].

Chai, CLL ;

Heath, GA ;

Huleatt, PB ;

O'Shea, GA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1999, (03) :389-391

[7] Redox sensitive epidithiodioxopiperazines in biological mechanisms of toxicity [J].

Chai, CLL ;

Waring, P .

REDOX REPORT, 2000, 5 (05) :257-264

[8] Nucleotide C3',4'-radical cations and the effect of a 2'-oxygen substituent. The DNA/RNA paradox [J].

Crich, D ;

Mo, XS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (01) :249-250

[9]

EICHNER RD, 1988, J BIOL CHEM, V263, P3772

[10] CRYSTAL STRUCTURE OF GLIOTOXIN [J].

FRIDRICH.J ;

MATHIESO.AM .

ACTA CRYSTALLOGRAPHICA, 1967, 23 :439-&