title: Synthesis and application of a 5'-aldehyde phosphoramidite for covalent attachment of DNA to biomolecules.
abstract: We recently reported the use of covalently attached DNA as a structural constraint for rational control of macromolecular conformation. Reductive amination was employed to attach each strand of the duplex DNA constraint to RNA, utilizing an aldehyde tethered to the 5'-terminus of the DNA. Here we describe the synthesis of a thymidine phosphoramidite that has the 5'-tethered aldehyde masked as a 1,2-diol. We also describe optimized reductive amination conditions for linking 5'-aldehyde-DNA with 2'-amino-2'-deoxy-RNA. These procedures should be generally applicable for attaching DNA to biomolecules.
authors.affiliation: Department of Chemistry, University of Illinois at Urbana-Champaign, 600 South Mathews Avenue, Urbana, Illinois 61801, USA.
authors.forename: Chandrasekhar V
authors.initials: CV
authors.lastname: Miduturu
authors.forename: Scott K
authors.initials: SK
authors.lastname: Silverman
mesh_terms: D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry; D000588:Amines / Q000737:chemistry; D004247:DNA / Q000737:chemistry / Q000378:metabolism*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D009943:Organophosphorus Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D012313:RNA / Q000737:chemistry / Q000378:metabolism*
chemical_list: D000447:Aldehydes; D000588:Amines; D009943:Organophosphorus Compounds; C434331:phosphoramidite; D012313:RNA; D004247:DNA