title: Preparation of base-deuterated 2'-deoxyadenosine nucleosides and their site-specific incorporation into DNA.
abstract: We report a four-step synthesis of 2'-deoxy-2-deuteroadenosine from 2'-deoxyadenosine in 38% overall yield. The more accessible 2'-deoxy-8-deuteroadenosine was also prepared and incorporated into DNA by automated solid phase synthesis (80% deuterium) using N6-benzoyl-2'-deoxy-8-deuteroadenosine-3'-O-(2-cyanoethyl-N,N-diisopropylphosphoramidite) in combination with acetyl-protected deoxycytidine and phenoxyacetyl-protected purine phosphoramidites.
authors.affiliation: Department of Chemistry, University of Washington, Seattle 98195-1700, USA.
authors.forename: P
authors.initials: P
authors.lastname: Chirakul
authors.forename: J R
authors.initials: JR
authors.lastname: Litzer
authors.lastname: Sigurdsson STh
mesh_terms: D001671:Biochemistry / Q000379:methods; D004247:DNA / Q000737:chemistry*; D003839:Deoxyadenosines / Q000737:chemistry*; D003903:Deuterium / Q000737:chemistry*; D007553:Isotope Labeling / Q000379:methods; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D003839:Deoxyadenosines; D009705:Nucleosides; D004247:DNA; D003903:Deuterium; C058118:2'-deoxyadenosine