Submonomeric Strategy with Minimal Protection for the Synthesis of C(2)-Modified Peptide Nucleic Acids

[Image: see text] A novel synthesis of C(2)-modified peptide nucleic acids (PNAs) is proposed, using a submonomeric strategy with minimally protected building blocks, which allowed a reduction in the required synthetic steps. N(3)-unprotected, d-Lys- and d-Arg-based backbones were used to obtain pos...

Descripción completa

Detalles Bibliográficos
Autores principales: Volpi, Stefano, Rozzi, Andrea, Rivi, Nicola, Neri, Martina, Knoll, Wolfgang, Corradini, Roberto
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7880566/
https://www.ncbi.nlm.nih.gov/pubmed/33417460
http://dx.doi.org/10.1021/acs.orglett.0c04116
_version_ 1783650724853317632
author Volpi, Stefano
Rozzi, Andrea
Rivi, Nicola
Neri, Martina
Knoll, Wolfgang
Corradini, Roberto
author_facet Volpi, Stefano
Rozzi, Andrea
Rivi, Nicola
Neri, Martina
Knoll, Wolfgang
Corradini, Roberto
author_sort Volpi, Stefano
collection PubMed
description [Image: see text] A novel synthesis of C(2)-modified peptide nucleic acids (PNAs) is proposed, using a submonomeric strategy with minimally protected building blocks, which allowed a reduction in the required synthetic steps. N(3)-unprotected, d-Lys- and d-Arg-based backbones were used to obtain positively charged PNAs with high optical purity, as inferred from chiral GC measurements. “Chiral-box” PNAs targeting the G12D point mutation of the KRAS gene were produced using this method, showing improved sequence selectivity for the mutated- vs wild-type DNA strand with respect to unmodified PNAs.
format Online
Article
Text
id pubmed-7880566
institution National Center for Biotechnology Information
language English
publishDate 2021
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-78805662021-02-16 Submonomeric Strategy with Minimal Protection for the Synthesis of C(2)-Modified Peptide Nucleic Acids Volpi, Stefano Rozzi, Andrea Rivi, Nicola Neri, Martina Knoll, Wolfgang Corradini, Roberto Org Lett [Image: see text] A novel synthesis of C(2)-modified peptide nucleic acids (PNAs) is proposed, using a submonomeric strategy with minimally protected building blocks, which allowed a reduction in the required synthetic steps. N(3)-unprotected, d-Lys- and d-Arg-based backbones were used to obtain positively charged PNAs with high optical purity, as inferred from chiral GC measurements. “Chiral-box” PNAs targeting the G12D point mutation of the KRAS gene were produced using this method, showing improved sequence selectivity for the mutated- vs wild-type DNA strand with respect to unmodified PNAs. American Chemical Society 2021-01-08 2021-02-05 /pmc/articles/PMC7880566/ /pubmed/33417460 http://dx.doi.org/10.1021/acs.orglett.0c04116 Text en © 2021 The Authors. Published by American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
spellingShingle Volpi, Stefano
Rozzi, Andrea
Rivi, Nicola
Neri, Martina
Knoll, Wolfgang
Corradini, Roberto
Submonomeric Strategy with Minimal Protection for the Synthesis of C(2)-Modified Peptide Nucleic Acids
title Submonomeric Strategy with Minimal Protection for the Synthesis of C(2)-Modified Peptide Nucleic Acids
title_full Submonomeric Strategy with Minimal Protection for the Synthesis of C(2)-Modified Peptide Nucleic Acids
title_fullStr Submonomeric Strategy with Minimal Protection for the Synthesis of C(2)-Modified Peptide Nucleic Acids
title_full_unstemmed Submonomeric Strategy with Minimal Protection for the Synthesis of C(2)-Modified Peptide Nucleic Acids
title_short Submonomeric Strategy with Minimal Protection for the Synthesis of C(2)-Modified Peptide Nucleic Acids
title_sort submonomeric strategy with minimal protection for the synthesis of c(2)-modified peptide nucleic acids
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7880566/
https://www.ncbi.nlm.nih.gov/pubmed/33417460
http://dx.doi.org/10.1021/acs.orglett.0c04116
work_keys_str_mv AT volpistefano submonomericstrategywithminimalprotectionforthesynthesisofc2modifiedpeptidenucleicacids
AT rozziandrea submonomericstrategywithminimalprotectionforthesynthesisofc2modifiedpeptidenucleicacids
AT rivinicola submonomericstrategywithminimalprotectionforthesynthesisofc2modifiedpeptidenucleicacids
AT nerimartina submonomericstrategywithminimalprotectionforthesynthesisofc2modifiedpeptidenucleicacids
AT knollwolfgang submonomericstrategywithminimalprotectionforthesynthesisofc2modifiedpeptidenucleicacids
AT corradiniroberto submonomericstrategywithminimalprotectionforthesynthesisofc2modifiedpeptidenucleicacids

Ejemplares similares