Abstraction of deuterium from dideuteroglycine by aryl radical: A model for 1,4-benzene diradical reactions with proteins

被引：16

作者：

Braslau, R ^{[1
]}

Anderson, MO ^{[1
]}

机构：

[1] Univ Calif Santa Cruz, Dept Chem & Biochem, Santa Cruz, CA 95064 USA

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 24期

基金：

美国国家科学基金会;

关键词：

amino acids and derivatives; radicals and radical reactions; diynes; labelling;

D O I：

10.1016/S0040-4039(98)00791-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Aryl radicals are generated by oxidation of aryl hydrazine with PbO2 or via photolysis of aryl iodide. Abstraction of deuterium from dideuteroglycine derivatives is demonstrated as a model for the possible reaction of 1,4-aryl diradicals with amino acid residues in proteins. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：4227 / 4230

页数：4

共 15 条

[1] DEUTERATED AMINO ACIDS .I. SYNTHESIS OF GLYCINE-D AND RELATED DERIVATIVES [J].

BLOMQUIS.AT ;

HISCOCK, BF ;

HARPP, DN .

JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (01) :338-&

[2] Low-temperature preparations of unimolecular nitroxide initiators for ''living'' free radical polymerizations [J].

Braslau, R ;

Burrill, LC ;

Siano, M ;

Naik, N ;

Howden, RK ;

Mahal, LK .

MACROMOLECULES, 1997, 30 (21) :6445-6450

[3] Free-radical reactions in the synthesis of alpha-amino acids and derivatives [J].

Easton, CJ .

CHEMICAL REVIEWS, 1997, 97 (01) :53-82

[4] The chemistry of enediynes, enyne allenes and related compounds [J].

Grissom, JW ;

Gunawardena, GU ;

Klingberg, D ;

Huang, DH .

TETRAHEDRON, 1996, 52 (19) :6453-6518

[5] AZOESTER COMPOUNDS FOR INDUCING DNA CLEAVAGE UNDER PHYSIOLOGICAL CONDITIONS [J].

JEBARATNAM, DJ ;

KUGABALASOORIAR, S ;

CHEN, H ;

ARYA, DP .

TETRAHEDRON LETTERS, 1995, 36 (18) :3123-3126

[6] Fluorine substitution enhances the reactivity of substituted phenyl radicals toward organic hydrogen atom donors [J].

Li, RM ;

Smith, RL ;

Kenttamaa, HI .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (21) :5056-5061

[7] Ab initio calculation of hydrogen abstraction reactions of phenyl radical and p-benzyne [J].

Logan, CF ;

Chen, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (08) :2113-2114

[8] Synthetic and mechanistic studies on the azabicyclo[7.3.1]enediyne core and naphtho[2,3-h]quinoline portions of dynemicin A [J].

Magnus, P ;

Eisenbeis, SA ;

Fairhurst, RA ;

Iliadis, T ;

Magnus, NA ;

Parry, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (24) :5591-5605

[9] STUDIES ON THE THERMAL GENERATION AND REACTIVITY OF A CLASS OF (SIGMA,PI)-1,4-BIRADICALS [J].

MYERS, AG ;

DRAGOVICH, PS ;

KUO, EY .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (24) :9369-9386

[10] Toward site specificity of oxidative damage in proteins: C-H and C-C bond dissociation energies and reduction potentials of the radicals of alanine, serine, and threonine residues - An ab initio study [J].

Rauk, A ;

Yu, D ;

Armstrong, DA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (01) :208-217

← 1 2 →