Dakin-West reaction on 1-thyminyl acetic acid for the synthesis of 1, 3-bis(1-thyminyl)-2-propanone, a heteroaromatic compound with nucleopeptide-binding properties

This work deals with the Dakin-West synthesis, starting from the nucleoamino acid 1-thyminyl acetic acid, as well the NMR, ESI MS, and X-ray characterization of Aheteroaromatic compound denominated by us T2CO, comprising two thymine moieties anchored to A2-propanonic unit, the spectroscopic properties of which were studied by UV as Afunction of temperature and ionic strength. Preliminary binding-studies with molecules of biomedical interest such as nucleic acids and proteins, performed on samples containing T2CO, suggested that this molecule is able to interact very weakly with double-stranded RNA, whereas it does not seem to bind other nucleic acids or proteins. Moreover, by studies with fresh human serum we found that T 2CO is resistant to enzymatic degradation till 24 h, whereas UV metal binding-studies, performed using solutions of copper (II) chloride dihydrate and nickel (II) chloride hexahydrate, revealed Acertain ability of T 2CO to bind copper (II) cation. Finally, by CD spectroscopy we investigated the influence of T2CO on the already described supramolecular networks based on l-serine-containing nucleopeptides. More particularly, we found that T2CO is able to increase the level of structuration of the non-covalent supramolecular assembly of the chiral nucleopeptides, which is Afeature of remarkable interest for the development of innovative drug delivery tools. © 2012 Springer-Verlag.

Dakin-West reaction on 1-thyminyl acetic acid for the synthesis of 1, 3-bis(1-thyminyl)-2-propanone, a heteroaromatic compound with nucleopeptide-binding properties

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