DNA-Templated N(Me)-Alkoxyamine Glycosylation

[Image: see text] The potential of N(Me)-alkoxyamine glycosylation as a DNA-templated ligation has been studied. On a hairpin stem-template model, a notable rate enhancement and an increased equilibrium yield are observed compared to the corresponding reaction without a DNA catalyst. The N-glycosidi...

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Autores principales: Österlund, Tommi, Korhonen, Heidi, Virta, Pasi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2018
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6203178/
https://www.ncbi.nlm.nih.gov/pubmed/29513541
http://dx.doi.org/10.1021/acs.orglett.8b00113
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author Österlund, Tommi
Korhonen, Heidi
Virta, Pasi
author_facet Österlund, Tommi
Korhonen, Heidi
Virta, Pasi
author_sort Österlund, Tommi
collection PubMed
description [Image: see text] The potential of N(Me)-alkoxyamine glycosylation as a DNA-templated ligation has been studied. On a hairpin stem-template model, a notable rate enhancement and an increased equilibrium yield are observed compared to the corresponding reaction without a DNA catalyst. The N-glycosidic connection is dynamic at pH 5, whereas it becomes irreversible at pH 7. The N(Me)-alkoxyamine glycosylation may hence be an attractive pH controlled reaction for the assembly of DNA-based dynamic products.
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spelling pubmed-62031782018-11-05 DNA-Templated N(Me)-Alkoxyamine Glycosylation Österlund, Tommi Korhonen, Heidi Virta, Pasi Org Lett [Image: see text] The potential of N(Me)-alkoxyamine glycosylation as a DNA-templated ligation has been studied. On a hairpin stem-template model, a notable rate enhancement and an increased equilibrium yield are observed compared to the corresponding reaction without a DNA catalyst. The N-glycosidic connection is dynamic at pH 5, whereas it becomes irreversible at pH 7. The N(Me)-alkoxyamine glycosylation may hence be an attractive pH controlled reaction for the assembly of DNA-based dynamic products. American Chemical Society 2018-03-07 2018-03-16 /pmc/articles/PMC6203178/ /pubmed/29513541 http://dx.doi.org/10.1021/acs.orglett.8b00113 Text en Copyright © 2018 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 Österlund, Tommi
Korhonen, Heidi
Virta, Pasi
DNA-Templated N(Me)-Alkoxyamine Glycosylation
title DNA-Templated N(Me)-Alkoxyamine Glycosylation
title_full DNA-Templated N(Me)-Alkoxyamine Glycosylation
title_fullStr DNA-Templated N(Me)-Alkoxyamine Glycosylation
title_full_unstemmed DNA-Templated N(Me)-Alkoxyamine Glycosylation
title_short DNA-Templated N(Me)-Alkoxyamine Glycosylation
title_sort dna-templated n(me)-alkoxyamine glycosylation
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6203178/
https://www.ncbi.nlm.nih.gov/pubmed/29513541
http://dx.doi.org/10.1021/acs.orglett.8b00113
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AT virtapasi dnatemplatednmealkoxyamineglycosylation

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