DNA-Templated N(Me)-Alkoxyamine Glycosylation



: Tommi Österlund, Heidi Korhonen, Pasi Virta

Publisher: AMER CHEMICAL SOC

: 2018

: Organic Letters

: ORGANIC LETTERS

: ORG LETT

: 20

: 6

: 1496

: 1499

: 4

: 1523-7060

: 1523-7052

DOI: https://doi.org/10.1021/acs.orglett.8b00113


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 I may hence be an attractive pH controlled reaction for the assembly of DNA-based dynamic products.



Last updated on 2024-26-11 at 21:37