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DNA-Templated N(Me)-Alkoxyamine Glycosylation.

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

SUBMITTER: Osterlund T

PROVIDER: S-EPMC6203178 | biostudies-literature | 2018 Mar

REPOSITORIES: biostudies-literature

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DNA-Templated N(Me)-Alkoxyamine Glycosylation.

Österlund Tommi T Korhonen Heidi H Virta Pasi P

Organic letters 20180307 6

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. ...[more]

PMID: 29513541

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