Preparation of base-deuterated 2'-deoxyadenosine nucleosides and their site-specific incorporation into DNA.
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.
Chirakul
P
P
Department of Chemistry, University of Washington, Seattle 98195-1700, USA.
Litzer
J R
JR
Sigurdsson STh
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
D003839:Deoxyadenosines; D009705:Nucleosides; D004247:DNA; D003903:Deuterium; C058118:2'-deoxyadenosine