Synthesis and characterization of novel N-para-ferrocenyl benzoyl dipeptide esters

被引:22
作者
Savage, David
Alley, Steven R.
Goel, Alok
Hogan, Tara
Ida, Yoshiteru
Kelly, Paula N.
Lehmann, Laurent
Kenny, Peter T. M. [1 ]
机构
[1] Dublin City Univ, Sch Chem Sci, Dublin 9, Ireland
[2] Dublin City Univ, Natl Inst Cellular Biotechnol, Dublin 9, Ireland
[3] Showa Univ, Sch Pharmaceut Sci, Shinagawa Ku, Tokyo 1428555, Japan
关键词
ferrocene; bioorganometallic chemistry; tandem mass spectrometry; dipeptides; CV; ELECTROCHEMICAL ANION RECOGNITION; RAY CRYSTAL-STRUCTURES; AMINO-ACID ESTERS; STRUCTURAL-CHARACTERIZATION; METHYL-ESTER; REDOX; DERIVATIVES; CHAINS; PEPTIDES; FC;
D O I
10.1016/j.inoche.2006.06.013
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
N-para-ferrocenyl benzoyl dipeptide esters 2-5 were prepared by coupling para-ferrocenyl benzoic acid I to the dipeptide ethyl esters GlyGly(OEt) 2, GlyAla(OEt) 3, GlyLeu(OEt) 4 and GlyPhe(OEt) 5. The compounds were fully characterized by a range of NMR spectroscopic techniques.. mass spectrometry (ESI-MS, FABMS, MS/MS) and cyclic voltammetry (CV). The a(1) and b(1) ions appeared at one mass unit less than the expected mass in the tandem mass spectra. The CV curves of compounds 2-5 exhibited quasi-reversible redox behavior similar to the Fc/Fc(+) redox couple and displayed oxidation potential values in the 50-55 mV range, against the Fc/Fc+ redox couple. (C) 2006 Elsevier B.V. All rights reserved.
引用
收藏
页码:1267 / 1270
页数:4
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