5'-O-Tritylthymidine

• CAT Number: I020980
• CAS Number: 7791-71-1
• Molecular Formula: C29H28N2O5
• Molecular Weight: 484.55
• Purity: 98%
• Synonyms: 5'-O-Tritylthymidine; M13; Monotritylthymidine; M 13; M-13
• Solubility: Soluble in DMSO
• Appearance: Solid powder
• Storage: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
• IUPAC Name: 1-[(2R,4S,5R)-4-Hydroxy-5-(trityloxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• InChI: InChI=1S/C29H28N2O5/c1-20-18-31(28(34)30-27(20)33)26-17-24(32)25(36-26)19-35-29(21-11-5-2-6-12-21,22-13-7-3-8-14-22)23-15-9-4-10-16-23/h2-16,18,24-26,32H,17,19H2,1H3,(H,30,33,34)/t24-,25+,26+/m0/s1
• InChIKey: FZDHVUVGQXVYOP-JIMJEQGWSA-N
• SMILES: O=C1NC(C(C)=CN1[C@@H]2O[C@H](COC(C3=CC=CC=C3)(C4=CC=CC=C4)C5=CC=CC=C5)[C@@H](O)C2)=O

5′-O-Tritylthymidine (CAT: I020980) is a modified nucleoside compound that is commonly used in organic synthesis and as a building block in nucleic acid chemistry. It features a trityl group attached to the 5′-position of the thymidine molecule, which provides protection and stability to the nucleoside during synthetic processes. The trityl group can be selectively removed to expose the free hydroxyl group for further functionalization or incorporation into nucleic acid sequences. 5′-O-Tritylthymidine is widely utilized in the synthesis of oligonucleotides, nucleic acid probes, and other biologically active compounds. It serves as a valuable tool for researchers working in the field of molecular biology and nucleic acid-based diagnostics.

Reference

1: Golubovskaya VM, Palma NL, Zheng M, Ho B, Magis A, Ostrov D, Cance WG. A small-molecule inhibitor, 5′-O-tritylthymidine, targets FAK and Mdm-2 interaction, and blocks breast and colon tumorigenesis in vivo. Anticancer Agents Med Chem. 2013 May;13(4):532-45. PubMed PMID: 22292771; PubMed Central PMCID: PMC3625481.
2: Liekens S, Bronckaers A, Hernández AI, Priego EM, Casanova E, Camarasa MJ, Pérez-Pérez MJ, Balzarini J. 5′-O-tritylated nucleoside derivatives: inhibition of thymidine phosphorylase and angiogenesis. Mol Pharmacol. 2006 Aug;70(2):501-9. Epub 2006 May 4. PubMed PMID: 16675660.
3: Hernández AI, Balzarini J, Karlsson A, Camarasa MJ, Pérez-Pérez MJ. Acyclic nucleoside analogues as novel inhibitors of human mitochondrial thymidine kinase. J Med Chem. 2002 Sep 12;45(19):4254-63. PubMed PMID: 12213066.
4: Capron MA, McEldoon WL, Baenziger NC, Wiemer DF. Structure of a modified nucleoside, 3′ alpha-diethylphosphono-3′ beta-hydroxy-5′-O-tritylthymidine. Acta Crystallogr C. 1994 Feb 15;50 ( Pt 2):291-4. PubMed PMID: 8148096.