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

Amino Acids
Giovanni N RovielloCarlo Pedone

Abstract

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 a heteroaromatic compound denominated by us T(2)CO, comprising two thymine moieties anchored to a 2-propanonic unit, the spectroscopic properties of which were studied by UV as a function of temperature and ionic strength. Preliminary binding-studies with molecules of biomedical interest such as nucleic acids and proteins, performed on samples containing T(2)CO, 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(2)CO 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 a certain ability of T(2)CO to bind copper (II) cation. Finally, by CD spectroscopy we investigated the influence of T(2)CO on the already described supramolecular networks based on L-serine-containing nucleopeptides. More particularly, we found that T(2)CO is able to increase the level of structuration of the n...Continue Reading

References

Mar 27, 1998·The Journal of Peptide Research : Official Journal of the American Peptide Society·D KrzyzanowskaM Kochman
Aug 12, 2006·The Journal of Organic Chemistry·Khanh-Van Tran, David Bickar
Dec 25, 2007·Acta Crystallographica. Section A, Foundations of Crystallography·George M Sheldrick
Nov 6, 2008·Journal of Peptide Science : an Official Publication of the European Peptide Society·G N RovielloE Benedetti
Nov 3, 2009·FASEB Journal : Official Publication of the Federation of American Societies for Experimental Biology·Zhou FeiJing-Hua Yang

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Citations

Sep 10, 2013·International Journal of Molecular Sciences·Laura RicciottiRaffaele Cioffi
Jan 15, 2014·Bioorganic & Medicinal Chemistry·Giovanni N RovielloCarlo Pedone
Oct 8, 2013·Acta Crystallographica. Section E, Structure Reports Online·Giuseppina RovielloAngela Tuzi
Oct 11, 2013·Acta Crystallographica. Section E, Structure Reports Online·Giuseppina RovielloClaudio Ferone
Apr 8, 2015·International Journal of Molecular Sciences·Daniela Marasco, Pasqualina Liana Scognamiglio
Mar 17, 2015·International Journal of Pharmaceutics·Giovanni N RovielloValentina Roviello
Jun 5, 2013·Biological Chemistry·Giovanni N RovielloCarlo Pedone
Nov 20, 2016·Amino Acids·Giovanni N RovielloCaterina Vicidomini
Sep 9, 2013·Materials·Giuseppina RovielloOreste Tarallo
Jul 17, 2013·Materials·Francesco ColangeloRaffaele Cioffi
Jul 3, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Pasqualina Liana ScognamiglioGiovanni Nicola Roviello

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