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
Articolo
Data di Pubblicazione:
2008
Citazione:
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]
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.
Tipologia IRIS:
01 - Articolo su periodico
Keywords:
Amino acids; Conformational analysis; Folding; Peptides; Terpyridines
Elenco autori:
R. Annunziata, M. Benaglia, A. Puglisi, L. Raimondi, F. Cozzi
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