[4 + 2] and [2 + 4] cycloaddition reactions on single- and double-stranded DNA: a dual-reactive nucleoside

Here we report dual reactivity of diene-modified duplex DNA containing 5-(1,3-butadienyl)-2′-deoxyuridine “BDdU”. Normal-electron demand [4 + 2] cycloaddition proceeded upon addition of a maleimide, whereas inverse-electron demand [2 + 4] cycloaddition occurred upon addition of a tetrazine to give a...

Descripción completa

Detalles Bibliográficos
Autores principales: Bujalska, Anna, Basran, Kaleena, Luedtke, Nathan W.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: RSC 2022
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9175100/
https://www.ncbi.nlm.nih.gov/pubmed/35755194
http://dx.doi.org/10.1039/d2cb00062h
_version_ 1784722383279489024
author Bujalska, Anna
Basran, Kaleena
Luedtke, Nathan W.
author_facet Bujalska, Anna
Basran, Kaleena
Luedtke, Nathan W.
author_sort Bujalska, Anna
collection PubMed
description Here we report dual reactivity of diene-modified duplex DNA containing 5-(1,3-butadienyl)-2′-deoxyuridine “BDdU”. Normal-electron demand [4 + 2] cycloaddition proceeded upon addition of a maleimide, whereas inverse-electron demand [2 + 4] cycloaddition occurred upon addition of a tetrazine to give a novel, photoswitchable product.
format Online
Article
Text
id pubmed-9175100
institution National Center for Biotechnology Information
language English
publishDate 2022
publisher RSC
record_format MEDLINE/PubMed
spelling pubmed-91751002022-06-23 [4 + 2] and [2 + 4] cycloaddition reactions on single- and double-stranded DNA: a dual-reactive nucleoside Bujalska, Anna Basran, Kaleena Luedtke, Nathan W. RSC Chem Biol Chemistry Here we report dual reactivity of diene-modified duplex DNA containing 5-(1,3-butadienyl)-2′-deoxyuridine “BDdU”. Normal-electron demand [4 + 2] cycloaddition proceeded upon addition of a maleimide, whereas inverse-electron demand [2 + 4] cycloaddition occurred upon addition of a tetrazine to give a novel, photoswitchable product. RSC 2022-05-05 /pmc/articles/PMC9175100/ /pubmed/35755194 http://dx.doi.org/10.1039/d2cb00062h Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Bujalska, Anna
Basran, Kaleena
Luedtke, Nathan W.
[4 + 2] and [2 + 4] cycloaddition reactions on single- and double-stranded DNA: a dual-reactive nucleoside
title [4 + 2] and [2 + 4] cycloaddition reactions on single- and double-stranded DNA: a dual-reactive nucleoside
title_full [4 + 2] and [2 + 4] cycloaddition reactions on single- and double-stranded DNA: a dual-reactive nucleoside
title_fullStr [4 + 2] and [2 + 4] cycloaddition reactions on single- and double-stranded DNA: a dual-reactive nucleoside
title_full_unstemmed [4 + 2] and [2 + 4] cycloaddition reactions on single- and double-stranded DNA: a dual-reactive nucleoside
title_short [4 + 2] and [2 + 4] cycloaddition reactions on single- and double-stranded DNA: a dual-reactive nucleoside
title_sort [4 + 2] and [2 + 4] cycloaddition reactions on single- and double-stranded dna: a dual-reactive nucleoside
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9175100/
https://www.ncbi.nlm.nih.gov/pubmed/35755194
http://dx.doi.org/10.1039/d2cb00062h
work_keys_str_mv AT bujalskaanna 42and24cycloadditionreactionsonsingleanddoublestrandeddnaadualreactivenucleoside
AT basrankaleena 42and24cycloadditionreactionsonsingleanddoublestrandeddnaadualreactivenucleoside
AT luedtkenathanw 42and24cycloadditionreactionsonsingleanddoublestrandeddnaadualreactivenucleoside

Ejemplares similares