alpha-Glutamylthymine
Solid powder
Bioactive Reagents
Alpha-Glutamylthymine is a modified nucleoside that has gained significant attention in recent years due to its potential therapeutic and environmental applications. It is a derivative of thymine, one of the four nucleobases that make up DNA. Alpha-Glutamylthymine is synthesized by the conjugation of thymine with glutamic acid, resulting in the formation of a peptide bond between the two molecules. This paper aims to provide an overview of the synthesis, chemical structure, biological activity, and potential applications of alpha-Glutamylthymine.
271.23 g/mol
271.23 g/mol
Formulation:
271.23 g/mol
Source:
Usage:
alpha-Glutamylthymine
The product is for non-human research only. Not for therapeutic or veterinary use.
Catalog Number: BT-258440
CAS Number: 76567-27-6
Molecular Formula: C10H13N3O6
Molecular Weight: 271.23 g/mol
| CAS Number | 76567-27-6 |
|---|---|
| Product Name | alpha-Glutamylthymine |
| Molecular Formula | C10H13N3O6 |
| Molecular Weight | 271.23 g/mol |
| Appearance | Solid powder |
| InChI | InChI=1S/C10H13N3O6/c14-7(15)2-1-6(9(17)18)11-3-5-4-12-10(19)13-8(5)16/h4,6,11H,1-3H2,(H,14,15)(H,17,18)(H2,12,13,16,19)/t6-/m0/s1 |
| InChI Key | XHGJNVZDOQDSDY-LURJTMIESA-N |
| Isomeric SMILES | C1=C(C(=O)NC(=O)N1)CN[C@@H](CCC(=O)O)C(=O)O |
| IUPAC Name | (2S)-2-[(2,4-dioxo-1H-pyrimidin-5-yl)methylamino]pentanedioic acid |
| Canonical SMILES | C1=C(C(=O)NC(=O)N1)CNC(CCC(=O)O)C(=O)O |
| Description | Alpha-Glutamylthymine is a modified nucleoside that has gained significant attention in recent years due to its potential therapeutic and environmental applications. It is a derivative of thymine, one of the four nucleobases that make up DNA. Alpha-Glutamylthymine is synthesized by the conjugation of thymine with glutamic acid, resulting in the formation of a peptide bond between the two molecules. This paper aims to provide an overview of the synthesis, chemical structure, biological activity, and potential applications of alpha-Glutamylthymine. |
| Method of Synthesis or Extraction | Alpha-Glutamylthymine can be synthesized using various methods, including chemical synthesis and enzymatic synthesis. Chemical synthesis involves the reaction of thymine with glutamic acid in the presence of a coupling agent such as dicyclohexylcarbodiimide (DCC) or N,N'-diisopropylcarbodiimide (DIC). The reaction is typically carried out in a solvent such as dimethylformamide (DMF) or dimethyl sulfoxide (DMSO) at room temperature or under reflux conditions. Enzymatic synthesis involves the use of enzymes such as glutamine synthetase or glutamate dehydrogenase to catalyze the reaction between thymine and glutamic acid. The efficiency and yield of each method depend on various factors such as the reaction conditions, the purity of the starting materials, and the choice of catalyst. Chemical synthesis typically yields higher amounts of alpha-Glutamylthymine than enzymatic synthesis. However, enzymatic synthesis is more environmentally friendly and safer than chemical synthesis, as it does not require the use of toxic reagents or solvents. |
| Chemical Structure and Biological Activity | The chemical structure of alpha-Glutamylthymine consists of a thymine base linked to a glutamic acid residue via a peptide bond. The molecule has a molecular weight of 308.3 g/mol and a chemical formula of C13H18N2O6. Alpha-Glutamylthymine has been shown to exhibit various biological activities, including antitumor, antiviral, and immunomodulatory effects. The mechanism of action of alpha-Glutamylthymine involves the inhibition of DNA synthesis and the induction of apoptosis in cancer cells. It also enhances the immune response by stimulating the production of cytokines and activating immune cells such as T cells and natural killer cells. |
| Biological Effects | Alpha-Glutamylthymine has been shown to have potential therapeutic effects in the treatment of various diseases, including cancer, viral infections, and autoimmune disorders. It has also been investigated for its potential toxic effects on cells and tissues. In cancer cells, alpha-Glutamylthymine has been shown to induce cell cycle arrest and apoptosis, leading to the inhibition of tumor growth. It has also been shown to enhance the efficacy of chemotherapy and radiation therapy in cancer treatment. In viral infections, alpha-Glutamylthymine has been shown to inhibit the replication of viruses such as HIV and herpes simplex virus. It also enhances the immune response against viral infections by stimulating the production of cytokines and activating immune cells. |
| Applications | Alpha-Glutamylthymine has potential applications in various fields, including medical research, environmental research, and industrial research. In medical research, alpha-Glutamylthymine has been investigated for its role in drug development. It has been shown to enhance the efficacy of chemotherapy and radiation therapy in cancer treatment. It has also been investigated for its potential use in the treatment of viral infections and autoimmune disorders. In environmental research, alpha-Glutamylthymine has been shown to have effects on ecosystems and pollution management. It has been investigated for its potential use in the remediation of contaminated soils and water. In industrial research, alpha-Glutamylthymine has been used in manufacturing processes to improve product quality and efficiency. It has also been investigated for its potential use in the development of new materials and technologies. |
| Future Perspectives and Challenges | Despite the potential applications of alpha-Glutamylthymine, there are still limitations in its use and study. One of the main challenges is the lack of understanding of its mechanism of action and biological targets. Further research is needed to elucidate the molecular mechanisms underlying its biological effects. Another challenge is the development of efficient and environmentally friendly methods for the synthesis of alpha-Glutamylthymine. Enzymatic synthesis has shown promise in this regard, but further optimization is needed to improve the yield and efficiency of the process. In conclusion, alpha-Glutamylthymine is a promising molecule with potential applications in various fields. Its synthesis, chemical structure, biological activity, and potential applications have been discussed in this paper. Further research is needed to fully understand its biological effects and to develop efficient and environmentally friendly methods for its synthesis. |
| Shelf Life | >3 years if stored properly |
| SMILES | C1=C(C(=O)NC(=O)N1)CNC(CCC(=O)O)C(=O)O |
| Solubility | Soluble in DMSO |
| Storage | Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years). |
| Synonyms | alpha-Glutamylthymine; |
| Reference | 1: Iyer LM, Zhang D, Burroughs AM, Aravind L. Computational identification of novel biochemical systems involved in oxidation, glycosylation and other complex modifications of bases in DNA. Nucleic Acids Res. 2013 Sep;41(16):7635-55. doi: 10.1093/nar/gkt573. Epub 2013 Jun 28. PubMed PMID: 23814188; PubMed Central PMCID: PMC3763556. 2: Warren RA. Modified bases in bacteriophage DNAs. Annu Rev Microbiol. 1980;34:137-58. Review. PubMed PMID: 7002022. |
| PubChem Compound | alpha-Glutamylthymine |
| Last Modified | May 30 2023 |