期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2014, 期 8, 页码 1741-1752出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201301765
关键词
Sensors; EPR spectroscopy; Magnetic properties; Amino acids; Peptides; Protein modifications; Protein folding
资金
- C'Nano NOVATECS [IF-08-1453/R]
- Fondazione CARIPARO (Progetti di Eccellenza)
To expand the presently extremely limited repertoire of known nitronyl nitroxide -amino acids, we report here the synthesis of a novel, conformationally constrained, quaternary, chiral residue, Aic(CN), and its subsequent conversion into a blue-colored, imidazolinyl nitronyl nitroxide-bearing -amino acid, Aic(NN). Deprotection and peptide coupling reactions were examined. The configurational assignment of Aic(NN) was achieved by X-ray crystallographic analysis of an appropriate tripeptide. This latter investigation, accompanied by an IR absorption conformational analysis, strongly supports the view that the Aic(NN) residue is an efficient peptide turn former. Numerous spectroscopic and magnetic properties of its derivatives and the tripeptide are also described. Of particular relevance for future applications are its UV/Vis absorption, NMR, and EPR signatures.
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