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Synthesis and Enzymatic Incorporation of Modified Deoxyadenosine Triphosphates
Author(s) -
Lam Curtis,
Hipolito Christopher,
Perrin David M.
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200800381
Subject(s) - chemistry , deoxyadenosine , deoxyribozyme , imidazole , stereochemistry , combinatorial chemistry , nucleotide , nucleophile , nucleophilic substitution , nucleoside , catalysis , dna , organic chemistry , biochemistry , gene
Several deoxyadenosine triphosphates containing modifications at the 8‐position have been synthesized. Suitably protected 8‐bromodeoxyadenosines were coupled with five imidazole‐containing moieties by nucleophilic aromatic substitution or Sonagashira coupling to give modified nucleosides that were then triphosphorylated. Incorporation assays were performed for these modified residues with many commercially available DNA polymerases, and it was found that two of the modified dATPs could be effectively taken up as substrates by Sequenase V2.0. These two residues are candidates for substrates in combinatorial selections in the search for improved catalysis from DNAzymes. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)