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Synthesis and structural characterization of metallated bioconjugates: C-terminal labeling of amino acids with ferroceneamine
Jorge L. Jios
1 ,
Norma N. Buceta
1 ,
Srecko I. Kirin
2 ,
Nils Metzler-Nolte
* 2, 3 ,
Carlos O. Della Védova
1, 4 ,
Thomas Weyhermüller
5
1  Laboratorio de Servicios a la Industria y al Sistema Científico (UNLP-CIC-CONICET), Departamento de Química, Facultad de Ciencias Exactas, Universidad Nacional de La Plata, 47 esq. 115, (1900) La Plata, República Argentina
2  Institute of Pharmacy and Molecular Biotechnology, University of Heidelberg, Im Neuenheimer Feld 364, D-69120 Heidelberg, Germany
3  Department of Chemistry, University of Bochum, Universitätsstraße 150, 44801 Bochum, Germany
4  CEQUINOR (UNLP-CONICET), Departamento de Química, Facultad de Ciencias Exactas, Universidad Nacional de La Plata, 47 esq. 115, (1900) La Plata, Argentina
5  Max Planck Institute for Bioinorganic Chemistry, Stiftstraße 34 - 36, D-45470 Mülheim an der Ruhr, Germany
Published: 30 November 2006 by MDPI in The 10th International Electronic Conference on Synthetic Organic Chemistry session Bioorganic Chemistry and Natural Products
https://doi.org/10.3390/ecsoc-10-01427
Abstract: Ferroceneamine, H2N-Fc, has been substituted to the C-terminus of 6 amino acids using the HBTU / HOBt coupling protocol. The synthesized bioconjugates Boc-Aaa-Fc, Aaa = Gly (1), Leu (2), Phe (3), Val (4), Cys(Acm) (5), Tyr(tBu) (6) (Acm = acetamidomethyl, tBu = t-buthyl), have been characterized by 1H NMR, 13C NMR EI-MS, EI-HRMS, UV and CD spectroscopies. In addition, a VT NMR study on 4 and the X-ray structure of 1 are presented.
Keywords: Amino acids, bioorganometallic chemistry, ferrocene, peptides, X-ray
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