EventsThe 10th International Electronic Conference on Synthetic Organic Chemistry
Event submissions
Published
with-doi10.3390/ecsoc-10-01427
This submission belongs to the session c. Bioorganic Chemistry and Natural Products of the event The 10th International Electronic Conference on Synthetic Organic Chemistry
Published date
30 Nov, 2006
Citation
Jorge L. Jios, Norma N. Buceta, Srecko I. Kirin, Nils Metzler-Nolte, Carlos O. Della Védova, Thomas Weyhermüller, Synthesis and structural characterization of metallated bioconjugates: C-terminal labeling of amino acids with ferroceneamine, in Proceedings of The 10th International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2006, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-10-01427
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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
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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