title: Regioselective synthesis of 1,3,5-13C3 and 2,4-13C2-labeled 2-deoxyribonolactones.
abstract: The synthesis of 1,3,5-13C3- and 2,4-13C2-labeled 5-O-bromobenzyl-2-deoxyribonolactones 2, precursors to 13C-enriched nucleoside phosphoramidites for solid-phase synthesis of DNA oligonucletides, is described. An equimolar combination of these two multiply labeled lactones affords a "population-labeled" mixture of isotopomers which exhibits an approximately 50-fold increase in the sensitivity of 13C-NMR compared to natural abundance measurements. The 13C-13C 2-bond and 4-bond coupling constants are reported for the lactones; all are <2Hz, confirming that this labeling scheme should be especially useful for NMR-relaxation measurements.
authors.affiliation: Department of Chemistry, Syracuse University, NY 13244-4100, USA.
authors.forename: P J
authors.initials: PJ
authors.lastname: Hatala
authors.forename: J
authors.initials: J
authors.lastname: Kallmerten
authors.forename: P N
authors.initials: PN
authors.lastname: Borer
mesh_terms: D001671:Biochemistry / Q000379:methods*; D002247:Carbon Isotopes; D007553:Isotope Labeling / Q000379:methods; D007783:Lactones / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D013400:Sugar Acids / Q000737:chemistry
chemical_list: D002247:Carbon Isotopes; D007783:Lactones; D013400:Sugar Acids; C056405:2,4,5-trihydroxypentanoic acid gamma-lactone