5522-55-4

Basic information

• Product Name: URACIL-15N2
• Synonyms: URACIL-15N2;URACIL (1,3-15N2);Uracil-1,3-15N2,99 atom % 15N;URACIL-1,3-15N2, 98+ ATOM % 15N;URACIL-13-15N2 99%
• CAS NO: 5522-55-4
• Molecular Formula: C₄H₄N₂O₂
• Molecular Weight: 114.1
• Product Categories: Alphabetical Listings;Stable Isotopes;U-Z
• Mol File: 5522-55-4.mol
• Article Data: 4

Chemical Properties

• Melting Point: >300 °C (dec.)(lit.)
• Appearance: /
• Density: 1.321g/cm³
• Refractive Index: 1.501
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Water (Slightly)
• CAS DataBase Reference: URACIL-15N2(CAS DataBase Reference)
• NIST Chemistry Reference: URACIL-15N2(5522-55-4)
• EPA Substance Registry System: URACIL-15N2(5522-55-4)

Safety Data

• Hazardous Substances Data: 5522-55-4(Hazardous Substances Data)

Usage

Uses

Uracil-15N2 can be used as a stable-isotopic standard to measure of post-replicative DNA metabolic and damage in brains of rodents. This compound can also be used for isotope tracing to determine the mechanism and stem-cell activity of 5-carboxycytosine decarboxylation.

InChI:InChI=1/C4H4N2O2/c7-3-1-2-5-4(8)6-3/h1-2H,(H2,5,6,7,8)/i5+1,6+1

Upstream product

• 2067-80-3 urea-15N₂ 
• 471-25-0 Propiolic acid 

Downstream Products

• 1391935-63-9 3',5'-(toluoyl)-2'-deoxy-(N₁,N₃-⁽¹⁵⁾N)-uridine 

Relevant articles and documents

5-Oxyacetic Acid Modification Destabilizes Double Helical Stem Structures and Favors Anionic Watson–Crick like cmo5U-G Base Pairs

Watson–Crick like G-U mismatches with tautomeric Genol or Uenol bases can evade fidelity checkpoints and thereby contribute to translational errors. The 5-oxyacetic acid uridine (cmo5U) modification is a base modification at the wobble position on tRNAs and is presumed to expand the decoding capability of tRNA at this position by forming Watson–Crick like cmo5Uenol-G mismatches. A detailed investigation on the influence of the cmo5U modification on structural and dynamic features of RNA was carried out by using solution NMR spectroscopy and UV melting curve analysis. The introduction of a stable isotope labeled variant of the cmo5U modifier allowed the application of relaxation dispersion NMR to probe the potentially formed Watson–Crick like cmo5Uenol-G base pair. Surprisingly, we find that at neutral pH, the modification promotes transient formation of anionic Watson–Crick like cmo5U?-G, and not enolic base pairs. Our results suggest that recoding is mediated by an anionic Watson–Crick like species, as well as bring an interesting aspect of naturally occurring RNA modifications into focus—the fine tuning of nucleobase properties leading to modulation of the RNA structural landscape by adoption of alternative base pairing patterns.

The economical synthesis of [2'-(13)C, 1,3-(15)N2]uridine; preliminary conformational studies by solid state NMR.

The synthesis of [2'-(13)C, 1,3-(15)N2]uridine 11 was achieved as follows. An epimeric mixture of D-[1-(13)C]ribose 3 and D-[1-(13)C]arabinose 4 was obtained in excellent yield by condensation of K13CN with D-erythrose 2 using a modification of the Kiliani-Fischer synthesis. Efficient separation of the two aldose epimers was pivotally achieved by a novel ion-exchange (Sm3+) chromatography method. D-[2-(13)C]Ribose 5 was obtained from D-[1-(13)C]arabinose 4 using a Ni(II) diamine complex (nickel chloride plus TEMED). Combination of these procedures in a general cycling manner can lead to the very efficient preparation of specifically labelled 13C-monosaccharides of particular chirality. 15N-labelling was introduced in the preparation of [2'-(13)C, 1,3-(15)N2]uridine 11 via [15N2]urea. Cross polarisation magic angle spinning (CP-MAS) solid-state NMR experiments using rotational echo double resonance (REDOR) were carried out on crystals of the labelled uridine to show that the inter-atomic distance between C-2' and N-1 is closely similar to that calculated from X-ray crystallographic data. The REDOR method will be used now to determine the conformation of bound substrates in the bacterial nucleoside transporters NupC and NupG.