DNA-Templated N(Me)-Alkoxyamine Glycosylation
Author(s) -
Tommi Österlund,
Heidi Korhonen,
Pasi Virta
Publication year - 2018
Publication title -
organic letters
Language(s) - Uncategorized
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.8b00113
Subject(s) - chemistry , glycosylation , glycosidic bond , dna , yield (engineering) , catalysis , ligation , combinatorial chemistry , biochemistry , microbiology and biotechnology , enzyme , materials science , metallurgy , biology
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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