Tuning Cross-Coupling Approaches to C3 Modification of 3-Deazapurines

[Image: see text] A general approach to C3 modification of purine scaffold through various types of cross-coupling reactions has been established. Tuning substrate electronics and reaction conditions resulted in the development of highly efficient sp(2)–sp, sp(2)–sp(2), and sp(2)–sp(3) cross-couplin...

Descripción completa

Detalles Bibliográficos
Autores principales: Weseliński, Łukasz J., Begoyan, Vagarshak, Ferrier, Alexis, Tanasova, Marina
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2017
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6045343/
https://www.ncbi.nlm.nih.gov/pubmed/30023537
http://dx.doi.org/10.1021/acsomega.7b01159
_version_ 1783339648188153856
author Weseliński, Łukasz J.
Begoyan, Vagarshak
Ferrier, Alexis
Tanasova, Marina
author_facet Weseliński, Łukasz J.
Begoyan, Vagarshak
Ferrier, Alexis
Tanasova, Marina
author_sort Weseliński, Łukasz J.
collection PubMed
description [Image: see text] A general approach to C3 modification of purine scaffold through various types of cross-coupling reactions has been established. Tuning substrate electronics and reaction conditions resulted in the development of highly efficient sp(2)–sp, sp(2)–sp(2), and sp(2)–sp(3) cross-coupling conditions for modification of 3-deazaadenine to access C3-modified adenine and hypoxanthine scaffolds. The optimized methodologies to access the corresponding 3-deazaadenosine phosphoramidites for solid-phase DNA synthesis have been demonstrated.
format Online
Article
Text
id pubmed-6045343
institution National Center for Biotechnology Information
language English
publishDate 2017
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-60453432018-07-16 Tuning Cross-Coupling Approaches to C3 Modification of 3-Deazapurines Weseliński, Łukasz J. Begoyan, Vagarshak Ferrier, Alexis Tanasova, Marina ACS Omega [Image: see text] A general approach to C3 modification of purine scaffold through various types of cross-coupling reactions has been established. Tuning substrate electronics and reaction conditions resulted in the development of highly efficient sp(2)–sp, sp(2)–sp(2), and sp(2)–sp(3) cross-coupling conditions for modification of 3-deazaadenine to access C3-modified adenine and hypoxanthine scaffolds. The optimized methodologies to access the corresponding 3-deazaadenosine phosphoramidites for solid-phase DNA synthesis have been demonstrated. American Chemical Society 2017-10-20 /pmc/articles/PMC6045343/ /pubmed/30023537 http://dx.doi.org/10.1021/acsomega.7b01159 Text en Copyright © 2017 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Weseliński, Łukasz J.
Begoyan, Vagarshak
Ferrier, Alexis
Tanasova, Marina
Tuning Cross-Coupling Approaches to C3 Modification of 3-Deazapurines
title Tuning Cross-Coupling Approaches to C3 Modification of 3-Deazapurines
title_full Tuning Cross-Coupling Approaches to C3 Modification of 3-Deazapurines
title_fullStr Tuning Cross-Coupling Approaches to C3 Modification of 3-Deazapurines
title_full_unstemmed Tuning Cross-Coupling Approaches to C3 Modification of 3-Deazapurines
title_short Tuning Cross-Coupling Approaches to C3 Modification of 3-Deazapurines
title_sort tuning cross-coupling approaches to c3 modification of 3-deazapurines
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6045343/
https://www.ncbi.nlm.nih.gov/pubmed/30023537
http://dx.doi.org/10.1021/acsomega.7b01159
work_keys_str_mv AT weselinskiłukaszj tuningcrosscouplingapproachestoc3modificationof3deazapurines
AT begoyanvagarshak tuningcrosscouplingapproachestoc3modificationof3deazapurines
AT ferrieralexis tuningcrosscouplingapproachestoc3modificationof3deazapurines
AT tanasovamarina tuningcrosscouplingapproachestoc3modificationof3deazapurines

Ejemplares similares