Synthetic approaches to nucleopeptides containing all four nucleobases, and nucleic acid-binding studies on a mixed-sequence nucleo-oligolysine

RSC Advances
Giovanni N Roviello, Domenica Musumeci

Abstract

In this article we describe two solid-phase synthetic routes to obtain a nucleo-oligolysine α-peptide containing all four natural nucleobases. The first one is based on the oligomerization of the nucleobase-containing monomers, easily synthesized as herein described. The second strategy has the advantage of avoiding the solution synthesis of the monomeric building blocks, leading to the final nucleopeptide by direct solid-phase couplings of the suitably protected nucleobases with the free amino groups on the growing peptide chain still anchored to the resin. Both strategies are general and can be applied to the synthesis of nucleopeptides having backbones formed by any other diamino acid moiety decorated with the four nucleobases. We also report the CD and UV studies on the hybridization properties of the obtained nucleopeptide, containing all four nucleobases on alternate lysines in the sequence, towards complementary DNA and RNA strands. The nucleo-oligolysine with a mixed-base sequence did not prove to bind complementary DNA, but was able to recognize the complementary RNA forming a complex with a higher melting temperature than that of the corresponding RNA/RNA natural duplex and comparable with that of the analogous PNA/RN...Continue Reading

References

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May 17, 2006·Clinical and Experimental Pharmacology & Physiology·Jasmine H P ChanW S Fred Wong
Dec 11, 2007·Nucleosides, Nucleotides & Nucleic Acids·Giovanni N RovielloCarlo Pedone
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Mar 12, 2011·Journal of Medicinal Chemistry·Giovanni N RovielloCarlo Pedone
Nov 5, 2011·Chemistry : a European Journal·Luca SimeoneDaniela Montesarchio
Jun 5, 2013·Biological Chemistry·Giovanni N RovielloCarlo Pedone
Jan 15, 2014·Bioorganic & Medicinal Chemistry·Giovanni N RovielloCarlo Pedone
Mar 1, 2014·Biochimica Et Biophysica Acta·Pasqualina Liana ScognamiglioDaniela Marasco
Mar 17, 2015·International Journal of Pharmaceutics·Giovanni N RovielloValentina Roviello
May 16, 2015·FASEB Journal : Official Publication of the Federation of American Societies for Experimental Biology·Concetta Di NataleDaniela Marasco
Jul 23, 2015·Beilstein Journal of Nanotechnology·Giovanni N RovielloMerab Mirtskhulava
Mar 15, 2016·RSC Advances·Giovanni N RovielloMichele Saviano

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Citations

Mar 15, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Na Chen, Juan Xie
Feb 26, 2019·Future Medicinal Chemistry·Caterina VicidominiGiovanni N Roviello
Feb 27, 2020·Chemical Reviews·Moran Frenkel-PinterLuke J Leman
Mar 7, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Nicola BorboneGiorgia Oliviero
May 20, 2020·Bioorganic Chemistry·Domenica MusumeciGiovanni N Roviello
Jul 3, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Pasqualina Liana ScognamiglioGiovanni Nicola Roviello
Nov 10, 2020·Journal of the American Chemical Society·Sebastian PomplunBradley L Pentelute

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Methods Mentioned

BETA
NMR
Circular
acetylation

Software Mentioned

Oligo
- Calculator

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