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Photoswitchable Oligonucleotides Containing Different Diarylethene-Modified Nucleotides

[Image: see text] Diarylethenes are a well-studied class of photoswitches and have often been linked to partner molecules to render them photoresponsive. Earlier, our lab developed a new type of diarylethenes in which the purine or pyrimidine base of a nucleoside or oligonucleotide serves as one of...

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Autores principales: Sarter, Christopher, Dey, Surjendu, Jäschke, Andres
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2019
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6682051/
https://www.ncbi.nlm.nih.gov/pubmed/31460326
http://dx.doi.org/10.1021/acsomega.9b01070
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author Sarter, Christopher
Dey, Surjendu
Jäschke, Andres
author_facet Sarter, Christopher
Dey, Surjendu
Jäschke, Andres
author_sort Sarter, Christopher
collection PubMed
description [Image: see text] Diarylethenes are a well-studied class of photoswitches and have often been linked to partner molecules to render them photoresponsive. Earlier, our lab developed a new type of diarylethenes in which the purine or pyrimidine base of a nucleoside or oligonucleotide serves as one of the two aryl residues of the photochromic system. Here, we report the synthesis of three different diarylethene-deoxyuridine phosphoramidites and their site-specific incorporation into oligodeoxynucleotides by solid-phase synthesis. Various DNA sequences carrying single or multiple, identical or different photoswitchable moieties are synthesized with high yield and purity. Upon UV irradiation, these DNA strands form a colored closed-ring isomer. The combination of different diarylethenes within one strand leads to an additive absorption spectrum. The photochromic DNA oligonucleotides are thermostable and photoreversible.
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spelling pubmed-66820512019-08-27 Photoswitchable Oligonucleotides Containing Different Diarylethene-Modified Nucleotides Sarter, Christopher Dey, Surjendu Jäschke, Andres ACS Omega [Image: see text] Diarylethenes are a well-studied class of photoswitches and have often been linked to partner molecules to render them photoresponsive. Earlier, our lab developed a new type of diarylethenes in which the purine or pyrimidine base of a nucleoside or oligonucleotide serves as one of the two aryl residues of the photochromic system. Here, we report the synthesis of three different diarylethene-deoxyuridine phosphoramidites and their site-specific incorporation into oligodeoxynucleotides by solid-phase synthesis. Various DNA sequences carrying single or multiple, identical or different photoswitchable moieties are synthesized with high yield and purity. Upon UV irradiation, these DNA strands form a colored closed-ring isomer. The combination of different diarylethenes within one strand leads to an additive absorption spectrum. The photochromic DNA oligonucleotides are thermostable and photoreversible. American Chemical Society 2019-07-15 /pmc/articles/PMC6682051/ /pubmed/31460326 http://dx.doi.org/10.1021/acsomega.9b01070 Text en Copyright © 2019 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 Sarter, Christopher
Dey, Surjendu
Jäschke, Andres
Photoswitchable Oligonucleotides Containing Different Diarylethene-Modified Nucleotides
title Photoswitchable Oligonucleotides Containing Different Diarylethene-Modified Nucleotides
title_full Photoswitchable Oligonucleotides Containing Different Diarylethene-Modified Nucleotides
title_fullStr Photoswitchable Oligonucleotides Containing Different Diarylethene-Modified Nucleotides
title_full_unstemmed Photoswitchable Oligonucleotides Containing Different Diarylethene-Modified Nucleotides
title_short Photoswitchable Oligonucleotides Containing Different Diarylethene-Modified Nucleotides
title_sort photoswitchable oligonucleotides containing different diarylethene-modified nucleotides
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6682051/
https://www.ncbi.nlm.nih.gov/pubmed/31460326
http://dx.doi.org/10.1021/acsomega.9b01070
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