Chemical Synthesis of 13C and 15N Labeled Nucleosides

Abstract

The chemical synthesis of 13 C and 15 N labeled nucleosides for site-specific incorporation in RNA or DNA oligonucleotides is herein reviewed. The review covers the following aspects: 1: single-and multiple site chemical 13 C and/or 15 N labeling of purine bases, 2: single-and multiple site chemical 13 C and/or 15 N labeling of pyrimidine bases, 3: single-and multiple site chemical 13 C labeling of the sugar residues.

Unambiguous structural elucidation of base‐modified purine nucleosides using NMR

“…15 N) can greatly enhance the power of NMR, in particular for the structural characterisation of macrobiomolecules such as DNA. [28,29] Two preparative protocols are generally used to introduce NMR-sensitive atoms in biological molecules: one is uniform labelling by cell culture [30] in which cells are treated with nutrient sources containing stable isotopes such as 13 C and 15 N to generate uniformly labelled biomolecules such as nucleotides that are then enzymatically phosphorylated and incorporated into oligonucleotides using enzymes and suitable templates. The other is site-specific labelling by chemical reaction in which an NMR-sensitive atom is placed at pre-determined position of the molecules.…”

Easy preparative scale syntheses of labelled xanthines: caffeine, theophylline and theobromine

“…35 This one step procedure using triethylorthoformate (or formamide, dimethylethylacetate, diethoxymethylacetate) is now widely used for both xanthines and purines. 21,36,37 Unfortunately, the combined yields of the two last steps were low (20%), leading to an extensive loss of labelled material. In order to overcome low yield, we have developed a second procedure starting from guanosine ( Figure 4).…”

Combined experimental and computational study of W(II), Ru(II), Pt(IV) and Cu(I) amine and amido complexes using 15N NMR spectroscopy

“…In fact, despite increased use of 15 N NMR spectroscopy in the study of solid-state and biological systems [64][65][66][67][68][69][70][71][72], the application of 15 N NMR spectroscopy to solution phase transition metal chemistry is relatively rare [73][74][75]. The dearth of 15 N NMR data for metal amido (and related) complexes is due in large part to the low natural abundance and low sensitivity of the 15 N nucleus [73].…”