A Chemical Approach to Introduce 2,6-Diaminopurine and 2-Aminoadenine Conjugates into Oligonucleotides without Need for Protecting Groups

[Image: see text] We report a simple, postsynthetic strategy for synthesis of oligonucleotides containing 2,6-diaminopurine nucleotides and 2-aminoadenine conjugates using 2-fluoro-6-amino-adenosine. The strategy allows introduction of 2,6-diaminopurine and other 2-amino group-containing ligands. Th...

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Autores principales: Madaoui, Mimouna, Datta, Dhrubajyoti, Wassarman, Kelly, Zlatev, Ivan, Egli, Martin, Ross, Bruce S., Manoharan, Muthiah
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9425559/
https://www.ncbi.nlm.nih.gov/pubmed/35973215
http://dx.doi.org/10.1021/acs.orglett.2c01848
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author Madaoui, Mimouna
Datta, Dhrubajyoti
Wassarman, Kelly
Zlatev, Ivan
Egli, Martin
Ross, Bruce S.
Manoharan, Muthiah
author_facet Madaoui, Mimouna
Datta, Dhrubajyoti
Wassarman, Kelly
Zlatev, Ivan
Egli, Martin
Ross, Bruce S.
Manoharan, Muthiah
author_sort Madaoui, Mimouna
collection PubMed
description [Image: see text] We report a simple, postsynthetic strategy for synthesis of oligonucleotides containing 2,6-diaminopurine nucleotides and 2-aminoadenine conjugates using 2-fluoro-6-amino-adenosine. The strategy allows introduction of 2,6-diaminopurine and other 2-amino group-containing ligands. The strongly electronegative 2-fluoro deactivates 6-NH(2) obviating the need for any protecting group on adenine, and simple aromatic nucleophilic substitution of fluorine makes reaction with aqueous NH(3) or R-NH(2) feasible at the 2-position.
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spelling pubmed-94255592022-08-31 A Chemical Approach to Introduce 2,6-Diaminopurine and 2-Aminoadenine Conjugates into Oligonucleotides without Need for Protecting Groups Madaoui, Mimouna Datta, Dhrubajyoti Wassarman, Kelly Zlatev, Ivan Egli, Martin Ross, Bruce S. Manoharan, Muthiah Org Lett [Image: see text] We report a simple, postsynthetic strategy for synthesis of oligonucleotides containing 2,6-diaminopurine nucleotides and 2-aminoadenine conjugates using 2-fluoro-6-amino-adenosine. The strategy allows introduction of 2,6-diaminopurine and other 2-amino group-containing ligands. The strongly electronegative 2-fluoro deactivates 6-NH(2) obviating the need for any protecting group on adenine, and simple aromatic nucleophilic substitution of fluorine makes reaction with aqueous NH(3) or R-NH(2) feasible at the 2-position. American Chemical Society 2022-08-16 2022-08-26 /pmc/articles/PMC9425559/ /pubmed/35973215 http://dx.doi.org/10.1021/acs.orglett.2c01848 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Madaoui, Mimouna
Datta, Dhrubajyoti
Wassarman, Kelly
Zlatev, Ivan
Egli, Martin
Ross, Bruce S.
Manoharan, Muthiah
A Chemical Approach to Introduce 2,6-Diaminopurine and 2-Aminoadenine Conjugates into Oligonucleotides without Need for Protecting Groups
title A Chemical Approach to Introduce 2,6-Diaminopurine and 2-Aminoadenine Conjugates into Oligonucleotides without Need for Protecting Groups
title_full A Chemical Approach to Introduce 2,6-Diaminopurine and 2-Aminoadenine Conjugates into Oligonucleotides without Need for Protecting Groups
title_fullStr A Chemical Approach to Introduce 2,6-Diaminopurine and 2-Aminoadenine Conjugates into Oligonucleotides without Need for Protecting Groups
title_full_unstemmed A Chemical Approach to Introduce 2,6-Diaminopurine and 2-Aminoadenine Conjugates into Oligonucleotides without Need for Protecting Groups
title_short A Chemical Approach to Introduce 2,6-Diaminopurine and 2-Aminoadenine Conjugates into Oligonucleotides without Need for Protecting Groups
title_sort chemical approach to introduce 2,6-diaminopurine and 2-aminoadenine conjugates into oligonucleotides without need for protecting groups
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9425559/
https://www.ncbi.nlm.nih.gov/pubmed/35973215
http://dx.doi.org/10.1021/acs.orglett.2c01848
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