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Synthesis and Enzymatic Incorporation of Modified Deoxyadenosine Triphosphates

TitleSynthesis and Enzymatic Incorporation of Modified Deoxyadenosine Triphosphates
Publication TypeJournal Article
Year of Publication2008
AuthorsLam, C, Hipolito, C, Perrin, DM
JournalEuropean Journal of Organic Chemistry
Pagination4915-4923
Date PublishedOct
Type of ArticleArticle
ISBN Number1434-193X
KeywordsAMINO-ACID, bioorganic chemistry, CATALYTIC REPERTOIRE, CLEAVING DNA ENZYME, DERIVATIVES, DNA, ENZYMES, FUNCTIONALITIES, HETEROCYCLES, IN-VITRO SELECTION, NUCLEIC-ACIDS, nucleotides, OLIGONUCLEOTIDES, PCR, POLYMERASES, SELEX
Abstract

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. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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