Synthesis of 2,2-and 2,5-disubstituted 1-oxyl pyrrolidine radicals as new homobifunctional cross-linking spin labels

被引:10
作者
Kálai, T
Jekö, J
Hubbell, WL
Hideg, K
机构
[1] Univ Pecs, Inst Organ & Med Chem, H-7602 Pecs, Hungary
[2] ICN Hungary Ltd, H-4440 Tiszavasvari, Hungary
[3] Univ Calif Los Angeles, Jules Stein Eye Inst, Los Angeles, CA 90095 USA
[4] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
来源
SYNTHESIS-STUTTGART | 2003年 / 13期
关键词
cross linking reagents; proteins; free radicals; Grignard reactions; nitrones; lithium;
D O I
10.1055/s-2003-41053
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of 2,2- and 2,5-disubstituted pyrrolidine nitroxide radicals starting from readily available nitrones 1, 11 is described. The stable radicals are acylating (10, 20), alkylating (7, 17) and thiol-specific (8, 18) reagents capable of producing crosslinks in proteins over distances in the range of 10-15 Angstrom.
引用
收藏
页码:2084 / 2088
页数:5
相关论文
共 27 条
[1]   A NOVEL REVERSIBLE THIOL-SPECIFIC SPIN LABEL - PAPAIN ACTIVE-SITE LABELING AND INHIBITION [J].
BERLINER, LJ ;
GRUNWALD, J ;
HANKOVSZKY, HO ;
HIDEG, K .
ANALYTICAL BIOCHEMISTRY, 1982, 119 (02) :450-455
[2]   Interaction of singlet molecular oxygen with double fluorescent and spin sensors [J].
Bilski, P ;
Hideg, K ;
Kálai, T ;
Bilska, MA ;
Chignell, CF .
FREE RADICAL BIOLOGY AND MEDICINE, 2003, 34 (04) :489-495
[3]   A new spin on protein dynamics [J].
Columbus, L ;
Hubbell, WL .
TRENDS IN BIOCHEMICAL SCIENCES, 2002, 27 (06) :288-295
[4]   Molecular motion of spin labeled side chains in α-helices:: Analysis by variation of side chain structure [J].
Columbus, L ;
Kálai, T ;
Jekö, J ;
Hideg, K ;
Hubbell, WL .
BIOCHEMISTRY, 2001, 40 (13) :3828-3846
[5]   VARIABLE ELECTRONIC-PROPERTIES OF THE CSNME2 GROUP [J].
CREARY, X ;
ALDRIDGE, T .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (13) :4280-4285
[6]  
Formaggio F, 2002, CHEM-EUR J, V8, P84, DOI 10.1002/1521-3765(20020104)8:1<84::AID-CHEM84>3.0.CO
[7]  
2-N
[8]  
HANKOVSZKY HO, 1980, SYNTHESIS-STUTTGART, P914
[9]  
HASSNER A, 1994, ORGANIC SYNTHESIS BA, P89
[10]   In vivo EPR imaging of the distribution and metabolism of nitroxide radicals in human skin [J].
He, GL ;
Samouilov, A ;
Kuppusamy, P ;
Zweier, JL .
JOURNAL OF MAGNETIC RESONANCE, 2001, 148 (01) :155-164