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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Detalles Bibliográficos
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
Descripción
Sumario:[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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