Ferrocene-histidine conjugates:: N-ferrocenoyl-histidyl(imN-ferrocenoyl)methylester:: synthesis and structure

被引:17
作者
Mandal, HS [1 ]
Kkaatz, HB [1 ]
机构
[1] Univ Saskatchewan, Dept Chem, Saskatoon, SK S7N 5C9, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
ferrocene; histidine; bioconjugate; amino acid; X-ray; electrochemistry;
D O I
10.1016/S0022-328X(03)00182-7
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The preparation of the new ferrocenoyl histidyl conjugates N-Fc-His-OMe (2) and N-Fc-His(epsilon-N-Fc)-OMe (3) and of a simple ferrocenoyl imidazole conjugate Fc-Im (4) is reported together with their spectroscopic and electrochemical characterization. The electrochemistry of 3 exhibits two fully reversible one-electron. oxidations, which are due to the stepwise oxidation of the two ferrocenoyl groups. The crystal structure of 3 shows the difference in the chemical environment of the two Fc groups, one being attached to the alpha-N and one being attached to the epsilon-N of the imidazole of histidine. There is no discernible intermolecular interaction present in the crystal structure. (C) 2003 Elsevier Science B.V. All rights reserved.
引用
收藏
页码:32 / 37
页数:6
相关论文
共 22 条
[1]   Synthesis of the first ferrocene-labeled dideoxynucleotide and its use for 3′-redox end-labeling of 5′-modified single-stranded oligonucleotides [J].
Anne, A ;
Blanc, B ;
Moiroux, J .
BIOCONJUGATE CHEMISTRY, 2001, 12 (03) :396-405
[2]   Ferrocenoyl glycylcystamine: organization into a supramolecular helicate structure [J].
Bediako-Amoa, I ;
Silerova, R ;
Kraatz, HB .
CHEMICAL COMMUNICATIONS, 2002, (20) :2430-2431
[3]   SANDWICHES BRING A NEW ELEMENT TO MOLECULAR RECOGNITION [J].
CONSTABLE, EC .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1991, 30 (04) :407-408
[4]  
Desiraju G. R, 1999, WEAK HYDROGEN BOND
[5]   Chiral ferrocene amines derived from amino acids and peptides:: Synthesis, solution and X-ray crystal structures and electrochemical investigations [J].
Hess, A ;
Sehnert, J ;
Weyhermüller, T ;
Metzler-Nolte, N .
INORGANIC CHEMISTRY, 2000, 39 (24) :5437-5443
[6]   Ferrocene-oligonucleotide conjugates for electrochemical probing of DNA [J].
Ihara, T ;
Maruo, Y ;
Takenaka, S ;
Takagi, M .
NUCLEIC ACIDS RESEARCH, 1996, 24 (21) :4273-4280
[7]   Gene sensor using ferrocenyl oligonucleotide [J].
Ihara, T ;
Nakayama, M ;
Murata, M ;
Nakano, K ;
Maeda, M .
CHEMICAL COMMUNICATIONS, 1997, (17) :1609-1610
[8]   Ferrocenoyl amino acids: A synthetic and structural study [J].
Kraatz, HB ;
Lusztyk, J ;
Enright, GD .
INORGANIC CHEMISTRY, 1997, 36 (11) :2400-2405
[9]   Electrochemical investigations of M-DNA self-assembled monolayers on gold electrodes [J].
Li, CZ ;
Long, YT ;
Kraatz, HB ;
Lee, JS .
JOURNAL OF PHYSICAL CHEMISTRY B, 2003, 107 (10) :2291-2296
[10]   Ferrocenic acid derivatives: towards rationalizing changes in the electronic and geometric structures [J].
Lin, L ;
Berces, A ;
Kraatz, HB .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1998, 556 (1-2) :11-20