Synthesis of a thymine-functionalized nucleoamino acid for the solid phase assembly of cationic nucleopeptides(485 views) Roviello GN, Musumeci D, D'Alessandro C, Pedone C
Istituto di Biostrutture e Bioimmagini, CNR, Via Mezzocannone 16, 80134, Naples, Italy, giovanni.roviello@cnr.it.
Dipartimento di Scienze Chimiche, Università di Napoli Federico II, 80126 Naples, Italy
Dipartimento Delle Scienze Biologiche, Università di Napoli Federico II, 80134 Naples, Italy
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Synthesis of a thymine-functionalized nucleoamino acid for the solid phase assembly of cationic nucleopeptides
In this work, we report the synthesis of a thymine-functionalized nucleoamino acid suitable for the solid phase synthesis of nucleopeptides. The monomer was obtained in solution starting from commercial compounds and after NMR ((1)H and (13)C) and ESIMS (positive ions) characterization it was used for the assembly of a cationic nucleopeptide obtained by sequentially introducing underivatized L-lysine units and nucleoamino acid monomers. After detachment from the resin, performed in acidic conditions, the oligomer was purified by HPLC and characterized by LC-ESIMS (positive ions) which confirmed the identity of the thymine-based nucleopeptide. The cationic nucleobase-containing peptide, well soluble in water, was studied by CD spectroscopy which allowed us to exclude any helical pre-organization of the nucleopeptide in the experimental conditions used. Furthermore, CD behavior of the oligomer at different temperatures was also studied as described in this work.
Synthesis of a thymine-functionalized nucleoamino acid for the solid phase assembly of cationic nucleopeptides