DNA-catalyzed glycosylation using aryl glycoside donors

Abstract

We report the identification by in vitro selection of Zn2+/Mn2+-dependent deoxyribozymes that glycosylate the 3′-OH of a DNA oligonucleotide. Both β and α anomers of aryl glycosides can be used as the glycosyl donors. Individual deoxyribozymes are each specific for a particular donor anomer.

DNA-Templated N(Me)-Alkoxyamine Glycosylation

“…Even reactions that are perceived to occur under dry conditions may work in aqueous media under hybridization-driven conditions. As an example, DNA-catalyzed glycosylation using aryl glycosides as donors has recently been described . However, for the self-assembled DNA-based supramolecular constructs, , dynamic combinatorial libraries, or for the models of self-replicating systems, − reversible dynamic reactions are of particular interest. − In addition, it would be beneficial if the reaction was biorthogonal and inducible by traceless stimuli, e.g., by a reasonable pH change, − oxidation, , or UV irradiation .…”

DNAmoreDB, a database of DNAzymes

“…The DNAzymes present in the database are classified according to the reaction that they catalyze, namely: RNA cleavage ( 1 , 7 ), DNA cleavage ( 9 , 22 ), RNA ligation ( 6 , 23–25 ), DNA ligation ( 24 , 26 ), DNA site-specific depurination ( 27 ), Porphyrin metalation ( 28 , 29 ), DNA phosphorylation ( 30 , 31 ), DNA capping ( 32 ), amino acid side-chain modification ( 9 , 33 , 34 ), thymine dimer repair ( 35 , 36 ), Copper-mediated Azide-Alkyne Cycloaddition (CuAAC) ( 37 ), Dephosphorylation ( 38 ), Diels-Alder ( 39 ), Tyrosine azido‐adenylylation ( 40 ), Modification of Phosphorylated Amino Acid Side Chains ( 41 , 42 ), Tyrosine Phosphorylation ( 43 , 44 ), Glycosylation ( 45 ), Reductive amination ( 46 ), Amide hydrolysis ( 47 , 48 ), and Ester hydrolysis ( 48 ). This classification allows users to apply filters while browsing the DNAzymes page, which can be accessed from the toolbar and from the quick links on the Home page.…”