The 2,2':6',2"-terpyridine scaffold has been identified as a conformationally discrete structural element potentially capable of inducing reversible folding in substituents, attached through suitable spacers to its 6,6"-positions, by metal complexation/ decomplexation or by protonation/deprotonation. The synthesis of some terpyridine–amino acids and terpyridine– dipeptide conjugates is described. The assembly of these conjugates has been achieved by connecting NH2- and CO2H- protected glycine, alanine, and valine residues or antiparallel oriented AlaGly/GlyAla chains to the terpyridine scaffold through phenylacetylene spacers. Preliminary experiments showed that upon addition of Zn2+ to the amino acid substituted transoid terpyridine systems, folded cisoid complexes were formed. Also, bis(protonation) of the dipeptide- substituted system resulted in the formation of a folded adduct. Reversibility of the folding process was shown by Zn2+ removal with triethylamine or deprotonation with aqueous ammonia.

Synthesis of some 2,2':6',2"-terpyridines disubstituted in positions 6 and 6" with head to tail oriented amino acids and dipeptide : a simple entry to a reversible inducer of folding in amino acid sequences / R. Annunziata, M. Benaglia, A. Puglisi, L. Raimondi, F. Cozzi. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 2008:23(2008), pp. 3976-3983. [10.1002/ejoc.200800433]

Synthesis of some 2,2':6',2"-terpyridines disubstituted in positions 6 and 6" with head to tail oriented amino acids and dipeptide : a simple entry to a reversible inducer of folding in amino acid sequences

R. Annunziata
Primo
;
M. Benaglia
Secondo
;
A. Puglisi;L. Raimondi
Penultimo
;
F. Cozzi
Ultimo
2008

Abstract

The 2,2':6',2"-terpyridine scaffold has been identified as a conformationally discrete structural element potentially capable of inducing reversible folding in substituents, attached through suitable spacers to its 6,6"-positions, by metal complexation/ decomplexation or by protonation/deprotonation. The synthesis of some terpyridine–amino acids and terpyridine– dipeptide conjugates is described. The assembly of these conjugates has been achieved by connecting NH2- and CO2H- protected glycine, alanine, and valine residues or antiparallel oriented AlaGly/GlyAla chains to the terpyridine scaffold through phenylacetylene spacers. Preliminary experiments showed that upon addition of Zn2+ to the amino acid substituted transoid terpyridine systems, folded cisoid complexes were formed. Also, bis(protonation) of the dipeptide- substituted system resulted in the formation of a folded adduct. Reversibility of the folding process was shown by Zn2+ removal with triethylamine or deprotonation with aqueous ammonia.
Amino acids; Conformational analysis; Folding; Peptides; Terpyridines
Settore CHIM/06 - Chimica Organica
2008
Article (author)
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/57266
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