thymine

Also known as 5-methylpyrimidine-2,4(1H,3H)-dione, 2,4-dihydroxy-5-methylpyrimidine, 5-methyl-2,4(1H,3H)-pyrimidinedione, 5-methyluracil, Thymin, 2,4(1H,3H)-Pyrimidinedione, 5-methyl-, 5-Methyl-2,4-dihydroxypyrimidine, 5-Methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

Thymine () (symbol T or Thy) is one of the four nucleotide bases in the nucleic acid of DNA that are represented by the letters G–C–A–T. The others are adenine, guanine, and cytosine. Thymine is also known as 5-methyluracil, a pyrimidine nucleobase. In RNA, thymine is replaced by the nucleobase uracil. Thymine was first isolated in 1893 by Albrecht Kossel and Albert Neumann from calf thymus glands, hence its name.

AI overview

Thymine is one of the four basic chemical building blocks that make up DNA, and it pairs with adenine to help store genetic information in living organisms. It's unique to DNA because in the similar molecule RNA, thymine is replaced by a related chemical called uracil.

AI-generated from the Wikipedia summary — may contain errors.

Chemical data

Formula: C5H6N2O2
Molecular weight: 126.11 g/mol
IUPAC name: 5-methyl-1H-pyrimidine-2,4-dione
SMILES: CC1=CNC(=O)NC1=O
InChIKey: RWQNBRDOKXIBIV-UHFFFAOYSA-N
XLogP: -0.6
Polar surface area: 58.2 Å²
H-bond donors: 2
H-bond acceptors: 2
Formal charge: 0

via PubChem

Research

18,572 papers

Thymine methyls and DNA-protein interactions.ReviewNucleic acids research · 1987Ivarie RDOI: 10.1093/nar/15.23.9975
A new method for sequencing DNA.Proceedings of the National Academy of Sciences of the United States of America · 1977Maxam AM, Gilbert WDOI: 10.1073/pnas.74.2.560
Thymine-Modified Silicones: A Bioinspired Approach to Cross-Linked, Recyclable Silicone Polymers.Biomacromolecules · 2023Voigt LJ, Tucker KE, Zelisko PMDOI: 10.1021/acs.biomac.3c00185
Thymine dissociation and dimer formation: A Raman and synchronous fluorescence spectroscopic study.Proceedings of the National Academy of Sciences of the United States of America · 2021Nagpal A, Dhankhar D, Cesario TC et al.DOI: 10.1073/pnas.2025263118
The Radiation Stability of Thymine in Solid H(2)O.Astrobiology · 2020Materese CK, Gerakines PA, Hudson RLDOI: 10.1089/ast.2019.2199
Photocrosslinking Probes Proximity of Thymine Modifiers Tethering Excitonically Coupled Dye Aggregates to DNA Holliday Junction.Molecules (Basel, Switzerland) · 2022Basu S, Cervantes-Salguero K, Yurke B et al.DOI: 10.3390/molecules27134006
[Thymine dimerization and survival of bacteria].Journal of molecular biology · 1962WACKER A, DELLWEG H, JACHERTS DDOI: 10.1016/s0022-2836(62)80022-9
Thymine and thymidine synthesis.Biochimica et biophysica acta · 1956BARNER HD, COHEN SS, GREEN MDOI: 10.1016/0006-3002(56)90252-9

via PubMed

Wikidata facts

Mass: 126.043

Show 4 more facts

canonical SMILES: CC1=CNC(=O)NC1=O
chemical formula: C₅H₆N₂O₂
Commons category: Thymine
melting point: 317

Sources (6)

via Wikidata · CC0

~4 min read

Article

8 sections

Contents

Derivation
Thymine imbalance causes mutation
Theoretical aspects
Synthesis
Laboratory synthesis
See also
References
External links

==Derivation== As its alternate name (5-methyluracil) suggests, thymine may be derived by methylation of uracil at the 5th carbon. In RNA, thymine is replaced with uracil in most cases. In DNA, thymine (T) binds to adenine (A) via two hydrogen bonds, thereby stabilizing the nucleic acid structures.