Next Article in Journal
Tracking Control of a Class of Chaotic Systems
Next Article in Special Issue
Convenient Asymmetric Synthesis of Fmoc-(S)-6,6,6-Trifluoro-Norleucine
Previous Article in Journal
Analytical Solutions of Fractional Klein-Gordon and Gas Dynamics Equations, via the (G/G)-Expansion Method
Previous Article in Special Issue
Occurrence of the d-Proline Chemotype in Enzyme Inhibitors
Article Menu
Issue 4 (April) cover image

Export Article

Open AccessArticle

Investigation of the Stereochemical-Dependent DNA and RNA Binding of Arginine-Based Nucleopeptides

1
DISTABiF, Università degli Studi della Campania “Luigi Vanvitelli”, via A. Vivaldi 43, 81100 Caserta, Italy
2
Departamento de Química Farmacéutica y Orgánica, Facultad de Farmacia, “Campus de Cartuja”, Granada University, 18071 Granada, Spain
3
Dipartimento di Farmacia, Università degli Studi di Napoli “Federico II”, via D. Montesano 49, 80131 Napoli, Italy
*
Authors to whom correspondence should be addressed.
Symmetry 2019, 11(4), 567; https://doi.org/10.3390/sym11040567
Received: 28 March 2019 / Revised: 12 April 2019 / Accepted: 17 April 2019 / Published: 19 April 2019
(This article belongs to the Special Issue Amino Acid Chirality)
  |  
PDF [5825 KB, uploaded 19 April 2019]
  |  

Abstract

Nucleopeptides represent an intriguing class of nucleic acid analogues, in which nucleobases are placed in a peptide structure. The incorporation of D- and/or L-amino acids in nucleopeptide molecules allows the investigation of the role of backbone stereochemistry in determining the formation of DNA and RNA hybrids. Circular Dichroism (CD) spectroscopic studies indicated the nucleopeptide as having fully l-backbone configuration-formed stable hybrid complexes with RNA molecules. Molecular Dynamics (MD) simulations suggested a potential structure of the complex resulting from the interaction between the l-nucleopeptide and RNA strand. From this study, both the backbone (ionics and H-bonds) and nucleobases (pairing and π-stacking) of the chiral nucleopeptide appeared to be involved in the hybrid complex formation, highlighting the key role of the backbone stereochemistry in the formation of the nucleopeptide/RNA complexes. View Full-Text
Keywords: nucleic acid; nucleopeptides; backbone stereochemistry; solid-phase synthesis; molecular dynamic simulation nucleic acid; nucleopeptides; backbone stereochemistry; solid-phase synthesis; molecular dynamic simulation
Figures

Figure 1

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).
SciFeed

Share & Cite This Article

MDPI and ACS Style

Tomassi, S.; Montalban, F.F.; Russo, R.; Novellino, E.; Messere, A.; Di Maro, S. Investigation of the Stereochemical-Dependent DNA and RNA Binding of Arginine-Based Nucleopeptides. Symmetry 2019, 11, 567.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Symmetry EISSN 2073-8994 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top