5'-(4,4'-Dimethoxytrityl)-5-iodo-2'-deoxyuridine
[CAS# 104375-88-4]

Identification

• Classification: Biochemical >> Nucleoside drugs >> Deoxynucleotides and their analogues
• Name: 5'-(4,4'-Dimethoxytrityl)-5-iodo-2'-deoxyuridine
• Synonyms: 2'-Deoxy-5'-O-DMT-5-iodouridine
• Molecular Formula: C₃₀H₂₉IN₂O₇
• Molecular Weight: 656.46
• CAS Registry Number: 104375-88-4
• SMILES: COC1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=C(C=C3)OC)OC[C@@H]4[C@H](C[C@@H](O4)N5C=C(C(=O)NC5=O)I)O

Properties

• Solubility: Insoluble (4.7E^-5 g/L) (25 ºC), Calc.^*
• Density: 1.60±0.1 g/cm³ (20 ºC 760 Torr), Calc.^*
• Melting point: >128 ºC (decomp)^**
• Index of Refraction: 1.689, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2016 ACD/Labs)

^** Hansen, Anders S.; Bioorganic & Medicinal Chemistry Letters 2011, V21(4), P1181-1184.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319
• Precautionary Statements: P264-P270-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362+P364-P501

Discovory and Applicatios

5'-(4,4'-Dimethoxytrityl)-5-iodo-2'-deoxyuridine is a nucleoside derivative that has been extensively used in molecular biology and biochemistry, primarily in the synthesis of oligonucleotides. This compound is a modified form of 2'-deoxyuridine, with the addition of a 4,4'-dimethoxytrityl (DMT) group at the 5' position and an iodine atom at the 5-position of the uracil base.

The DMT group, which is commonly used in the field of oligonucleotide synthesis, serves as a protective group during the solid-phase synthesis of oligonucleotides. It prevents unwanted reactions at the 5' hydroxyl group of the nucleoside, ensuring that the nucleoside is properly incorporated into the growing oligonucleotide chain. The iodine atom at the 5-position provides a site for selective reaction, allowing for further modifications or the incorporation of the nucleoside into a larger DNA or RNA molecule.

This chemical substance was first utilized in the 1980s as part of advancements in oligonucleotide synthesis techniques. The introduction of DMT-protected nucleosides greatly enhanced the efficiency and specificity of automated DNA synthesis, making it possible to synthesize longer and more complex sequences with higher yields. The 5'-(4,4'-Dimethoxytrityl)-5-iodo-2'-deoxyuridine has been a key component in improving the quality and reproducibility of synthetic oligonucleotides, which are fundamental in a wide range of applications in molecular biology.

One of the primary applications of 5'-(4,4'-Dimethoxytrityl)-5-iodo-2'-deoxyuridine is in the synthesis of modified oligonucleotides, which are used in various research fields, including genomics, diagnostics, and therapeutics. These modified oligonucleotides are used for tasks such as PCR (Polymerase Chain Reaction), DNA sequencing, antisense therapy, and RNA interference (RNAi) techniques. The iodine atom present in the compound allows for specific incorporation into oligonucleotide sequences, which can then be used to create probes or primers with increased sensitivity and specificity.

The compound is also employed in the development of certain types of oligonucleotide-based drugs, where it serves as a precursor in the synthesis of nucleosides or oligonucleotides with therapeutic potential. By modifying the base or backbone structure, researchers can enhance the stability, specificity, or binding affinity of these molecules, improving their efficacy in treating genetic diseases, infections, or cancer.

In summary, 5'-(4,4'-Dimethoxytrityl)-5-iodo-2'-deoxyuridine is a valuable reagent in the field of oligonucleotide synthesis. It is used to enhance the synthesis process by protecting functional groups and enabling the incorporation of modified bases. Its applications are integral to advancements in molecular biology and biotechnology, including the development of diagnostics, therapeutics, and research tools.