Uracil

• CAT Number: A000678
• CAS Number: 66-22-8
• Molecular Formula: C4H4N2O2
• Molecular Weight: 112.088
• Purity: ≥95%
• Synonyms: 66-22-8; 2,4-Dihydroxypyrimidine; 2,4(1H,3H)-Pyrimidinedione; Pyrimidine-2,4(1H,3H)-dione; 2,4-Pyrimidinediol
• Storage: -20°C
• IUPAC Name: 1H-pyrimidine-2,4-dione
• InChI: InChI=1S/C4H4N2O2/c7-3-1-2-5-4(8)6-3/h1-2H,(H2,5,6,7,8)
• InChIKey: ISAKRJDGNUQOIC-UHFFFAOYSA-N
• SMILES: C1=CNC(=O)NC1=O

Uracil is one of the four nucleobases in the nucleic acid of RNA that are represented by the letters A, G, C and U. The others are adenine (A), cytosine (C), and guanine (G). In RNA, uracil binds to adenine via two hydrogen bonds. In DNA, the uracil nucleobase is replaced by thymine. Uracil is a demethylated form of thymine. Uracil/’s use in the body is to help carry out the synthesis of many enzymes necessary for cell function through bonding with riboses and phosphates. Uracil serves as allosteric regulator and coenzyme for reactions in the human body and in plants. Uracil can be used to determine microbial contamination of tomatoes.

Reference

1: Bag SS, Yashmeen A. Uracil-amino acid as a scaffold for β-sheet
peptidomimetics: Study of photophysics and interaction with BSA protein. Bioorg
Med Chem Lett. 2017 Nov 10. pii: S0960-894X(17)31104-6. doi:
10.1016/j.bmcl.2017.11.017. [Epub ahead of print] PubMed PMID: 29153423.

2: Ilyina MG, Khamitov EM, Mustafin AG, Khursan SL. Controlled stabilization of
anionic forms of the uracil derivatives: A DFT study. J Mol Graph Model. 2017 Nov
11;79:65-71. doi: 10.1016/j.jmgm.2017.11.007. [Epub ahead of print] PubMed PMID:
29145035.

3: Wang Y, Liu D, Deng J, Wang Y, Xu J, Ye C. Loop-mediated isothermal
amplification using self-avoiding molecular recognition systems and antarctic
thermal sensitive uracil-DNA-glycosylase for detection of nucleic acid with
prevention of carryover contamination. Anal Chim Acta. 2017 Dec 15;996:74-87.
doi: 10.1016/j.aca.2017.10.022. Epub 2017 Oct 27. PubMed PMID: 29137710.

4: Yan Y, Qing Y, Pink JJ, Gerson SL. Loss of Uracil DNA Glycosylase Selectively
Re-sensitizes p53 Mutant and Deficient Cells to 5-FdU. Mol Cancer Res. 2017 Nov
8. pii: molcanres.0215.2017. doi: 10.1158/1541-7786.MCR-17-0215. [Epub ahead of
print] PubMed PMID: 29117941.

5: Anithaa VS, Vijayakumar S, Sudha M, Shankar R. Theoretical investigation on
hydrogen bond interaction of diketo/keto-enol form uracil and thymine tautomers
with intercalators. J Mol Model. 2017 Nov 6;23(12):333. doi:
10.1007/s00894-017-3476-8. PubMed PMID: 29105034.

6: Wu RR, Hamlow LA, He CC, Nei YW, Berden G, Oomens J, Rodgers MT. The intrinsic
basicity of the phosphate backbone exceeds that of uracil and thymine residues:
protonation of the phosphate moiety is preferred over the nucleobase for pdThd
and pUrd. Phys Chem Chem Phys. 2017 Nov 3. doi: 10.1039/c7cp05521h. [Epub ahead
of print] PubMed PMID: 29099122.

7: Deng X, Han L, Zhou J, Zhang H, Li Q. Discovery of triazole-based uracil
derivatives bearing amide moieties as novel dipeptidyl peptidase-IV inhibitors.
Bioorg Chem. 2017 Dec;75:357-367. doi: 10.1016/j.bioorg.2017.10.010. Epub 2017
Oct 23. PubMed PMID: 29096096.

8: Yang L, Yang L, Yu H, Liu L, Zhao X, Huang X. Conformational transitions of
uracil transporter UraA from Escherichia coli: a molecular simulation study. J
Biomol Struct Dyn. 2017 Oct 26:1-13. doi: 10.1080/07391102.2017.1388288. [Epub
ahead of print] PubMed PMID: 29072107.

9: Fennimore MA, Matsika S. Correction: Core-excited and shape resonances of
uracil. Phys Chem Chem Phys. 2017 Nov 1;19(42):29005-29006. doi:
10.1039/c7cp90241g. PubMed PMID: 29057412.

10: Kuznetsova AA, Iakovlev DA, Misovets IV, Ishchenko AA, Saparbaev MK,
Kuznetsov NA, Fedorova OS. Pre-steady-state kinetic analysis of damage
recognition by human single-strand selective monofunctional uracil-DNA
glycosylase SMUG1. Mol Biosyst. 2017 Oct 20. doi: 10.1039/c7mb00457e. [Epub ahead
of print] PubMed PMID: 29051947.