We synthesized by solution methods a water-soluble, terminally blocked heptapeptide based on five markedly helicogenic, C-alpha-tetrasubstituted alpha-amino acids C-alpha-methyl-L-norvalines and two strongly hydrophilic 2-amino-3-[1-(1,4,7-triazacyclononane)]-L-propanoic acid residues at positions 2 and 5. A Fourier transform infrared absorption and NMR analysis in deuterated chloroform and aqueous solutions of the heptapeptide and two side-chain protected synthetic precursors confirmed our working hypothesis that all oligomers are folded in the 3(10)-helical conformation. Based on these findings, we exploited this heptapeptide as a chiral reference compound for detailed electronic CD, vibrational CD, and Raman optical activity characterizations of the 3(10)-helix in aqueous solution.
The complete chirospectroscopic signature of the peptide 3(10)- helix in aqueous solution
TONIOLO, CLAUDIO;FORMAGGIO, FERNANDO;
2004
Abstract
We synthesized by solution methods a water-soluble, terminally blocked heptapeptide based on five markedly helicogenic, C-alpha-tetrasubstituted alpha-amino acids C-alpha-methyl-L-norvalines and two strongly hydrophilic 2-amino-3-[1-(1,4,7-triazacyclononane)]-L-propanoic acid residues at positions 2 and 5. A Fourier transform infrared absorption and NMR analysis in deuterated chloroform and aqueous solutions of the heptapeptide and two side-chain protected synthetic precursors confirmed our working hypothesis that all oligomers are folded in the 3(10)-helical conformation. Based on these findings, we exploited this heptapeptide as a chiral reference compound for detailed electronic CD, vibrational CD, and Raman optical activity characterizations of the 3(10)-helix in aqueous solution.Pubblicazioni consigliate
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