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DNA-Templated N(Me)-Alkoxyamine Glycosylation
Tekijät: Tommi Österlund, Heidi Korhonen, Pasi Virta
Kustantaja: AMER CHEMICAL SOC
Julkaisuvuosi: 2018
Journal: Organic Letters
Tietokannassa oleva lehden nimi: ORGANIC LETTERS
Lehden akronyymi: ORG LETT
Vuosikerta: 20
Numero: 6
Aloitussivu: 1496
Lopetussivu: 1499
Sivujen määrä: 4
ISSN: 1523-7060
eISSN: 1523-7052
DOI: https://doi.org/10.1021/acs.orglett.8b00113
Tiivistelmä
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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