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The synthesis and structural characterization of N-para-ferrocenyl benzoyl dipeptide esters: The X-ray crystal structure of N-{para-(ferrocenyl)benzoyl}-l-alanine-glycine ethyl ester
Authors:Alok Goel  David Savage  Tara Hogan  Sylvia M. Draper  Peter T.M. Kenny
Affiliation:a National Institute for Cellular Biotechnology, Dublin City University, Dublin 9, Ireland
b School of Chemical Sciences, Dublin City University, Dublin 9, Ireland
c Chemistry Department, Trinity College, Dublin 2, Ireland
Abstract:A series ofN-para-ferrocenyl benzoyl dipeptide esters 2-5 were prepared by coupling para-ferrocenyl benzoic acid (1) to the dipeptide ethyl esters using the conventional 1,3-dicyclohexylcarbodiimide (DCC), 1-hydroxybenzotriazole (HOBt) protocol. The dipeptides employed in the synthesis were Ala-Gly(OEt) (2), Ala-Ala(OEt) (3), Ala-Leu(OEt) (4) and Ala-Phe(OEt) (5). The compounds were fully characterized by a range of NMR spectroscopic techniques, electrospray ionization mass spectrometry (ESI-MS) and tandem mass spectrometry (MS/MS). In addition the X-ray crystal structure of the l-alanine-glycine derivative 2 has been determined.
Keywords:Ferrocene   Bioorganometallic chemistry   Tandem mass spectrometry   Dipeptides   X-ray
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