Introduction
C26H42N7O17P3S is a molecular species that contains twenty‑six carbon atoms, forty‑two hydrogen atoms, seven nitrogen atoms, seventeen oxygen atoms, three phosphorus atoms and one sulfur atom. The molecular formula indicates the presence of multiple phosphoryl groups and a sulfur atom incorporated into a phosphorous environment, suggesting that the compound belongs to the family of phosphorothioate‑modified oligonucleotides or nucleotide analogues. Such molecules are of interest in molecular biology, medicinal chemistry, and biotechnology because the phosphorothioate modification confers resistance to nucleases and enhances binding affinity for target nucleic acids. The compound has a calculated molecular weight of approximately 851.7 g mol⁻¹, making it a relatively large, polar, and hydrophilic entity that is typically handled in aqueous or aqueous–organic mixtures.
Classification and Nomenclature
Chemical Classification
Within the broader classification of organic compounds, C26H42N7O17P3S is most accurately described as a phosphorothioate‑modified oligonucleotide fragment. The presence of three phosphate groups indicates that the molecule is a triphosphate or a diester containing a terminal triphosphate moiety. The sulfur atom replaces one of the non‑bridging oxygen atoms in a phosphate group, a modification commonly employed to increase metabolic stability of nucleic acid therapeutics.
IUPAC Considerations
In accordance with IUPAC recommendations for nucleoside phosphates, the compound could be described using a combination of the base, sugar, and phosphate descriptors. A tentative IUPAC name would include the base identities, the 2′,3′‑bisphosphorothioate linkage, and the terminal triphosphate. However, due to the absence of a canonical structural description, the formula is often referenced by its empirical representation or by a proprietary code used in pharmaceutical literature.
Chemical Structure
General Framework
The backbone of the molecule is built from two nucleoside units connected through a phosphorothioate linkage. Each nucleoside contributes a sugar ring (deoxyribose or ribose) and a nitrogenous base. The sulfur atom is situated in the phosphorous center of the bridge, creating a P–S bond that replaces an O–P bond in the natural phosphate. A terminal triphosphate is attached to one end of the molecule, with two of the phosphates forming conventional diester linkages and the third phosphate providing the 3′‑end of the nucleotide chain.
Conformational Features
Phosphorothioate linkages exhibit stereochemical complexity; each phosphorous atom can exist as a chiral center, yielding multiple diastereomers. The presence of three phosphate groups results in a mixture of stereochemical isomers that must be characterized using chiral chromatography or stereospecific NMR techniques. The base–base interactions between the two nucleobases are typically Watson–Crick or Hoogsteen pairing motifs, which can influence the overall three‑dimensional conformation of the fragment in solution.
Synthesis and Preparation
Overview of Synthetic Strategy
The synthesis of C26H42N7O17P3S involves several stages: preparation of individual nucleoside phosphoramidites, formation of the phosphorothioate linkage, incorporation of the terminal triphosphate, and purification of the final product. Solid‑phase phosphoramidite chemistry is the most common route, allowing stepwise addition of nucleoside units and controlled introduction of the phosphorothioate modification.
Stepwise Synthesis
- Phosphoramidite Preparation: Individual nucleosides are converted to their 5′‑O‑(2‑(4,4′‑dimethoxytrityl)ethoxy)phosphoramidite derivatives, using standard coupling reagents such as 1,2‑ethanedithiol and 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