7'-O-DMT-morpholino uracil
[CAS# 1127343-02-5]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound
• Name: 7'-O-DMT-morpholino uracil
• Synonyms: 1-[(2R,6S)-6-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]morpholin-2-yl]pyrimidine-2,4-dione
• Molecular Formula: C₃₀H₃₁N₃O₆
• Molecular Weight: 529.58
• CAS Registry Number: 1127343-02-5
• SMILES: COC1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=C(C=C3)OC)OC[C@@H]4CNC[C@@H](O4)N5C=CC(=O)NC5=O

Discovory and Applicatios

7'-O-DMT-morpholino uracil is a synthetic nucleoside analog with a distinctive structure that combines a uracil base with a morpholine ring and a 4,4'-dimethoxytrityl (DMT) protecting group. This molecule serves as an essential building block in nucleotide synthesis, particularly in the development of morpholino oligonucleotides (MOs), which are used in gene silencing and therapeutic applications. Its structure is specifically designed to resist nuclease degradation, making it particularly valuable for applications in molecular biology and pharmacology.

The discovery of nucleoside analogs like 7'-O-DMT-morpholino uracil is rooted in the search for stable, versatile molecules that can mimic the natural nucleotides used in DNA and RNA synthesis. The incorporation of the DMT group as a protecting moiety allows chemists to control the addition of nucleotides selectively, enabling efficient synthesis of morpholino oligonucleotides through solid-phase synthesis techniques. This approach to nucleotide synthesis emerged in the late 20th century, largely driven by research on synthetic gene regulation mechanisms.

The unique properties of 7'-O-DMT-morpholino uracil make it an effective component in creating morpholino oligonucleotides. These MOs are characterized by a backbone where natural phosphodiester linkages are replaced with phosphorodiamidate linkages, significantly enhancing the molecule’s resistance to enzymatic degradation. As a result, 7'-O-DMT-morpholino uracil contributes to oligonucleotides that retain functionality in vivo, making them ideal candidates for gene silencing applications such as antisense therapy and targeted gene inhibition. These therapeutic applications involve binding to specific mRNA sequences to prevent the translation of disease-related proteins, a strategy that has shown promise in treating conditions like Duchenne muscular dystrophy and certain cancers.

In addition to its therapeutic uses, 7'-O-DMT-morpholino uracil plays an important role in research settings, where it is used to create morpholino-based probes for studying gene function. Researchers employ these probes in gene knockdown studies, allowing them to investigate the effects of reduced gene expression on cellular and developmental processes. This molecule’s contribution to the field of synthetic nucleotides has enabled significant advances in genomics and functional genomics, providing scientists with a reliable tool to modulate gene expression precisely.

The stability and compatibility of 7'-O-DMT-morpholino uracil in solid-phase synthesis have made it a staple in laboratories focused on genetic research and therapeutic innovation. As synthetic biology and gene therapy fields continue to expand, compounds like this nucleoside analog will likely remain central to developing safe and effective gene-modulating agents. This molecule exemplifies how tailored chemical modifications to nucleosides can yield powerful tools for both fundamental research and medical applications.