A1 Refereed original research article in a scientific journal
DNA-Templated N(Me)-Alkoxyamine Glycosylation
Authors: Tommi Österlund, Heidi Korhonen, Pasi Virta
Publisher: AMER CHEMICAL SOC
Publication year: 2018
Journal: Organic Letters
Journal name in source: ORGANIC LETTERS
Journal acronym: ORG LETT
Volume: 20
Issue: 6
First page : 1496
Last page: 1499
Number of pages: 4
ISSN: 1523-7060
eISSN: 1523-7052
DOI: https://doi.org/10.1021/acs.orglett.8b00113
Abstract
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.
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.
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