1172-42-5Relevant articles and documents
A Novel Synthesis of Nucleoside 5'-Triphosphates
Mishra, Nrusingha C.,Broom, Arthur D.
, p. 1276 - 1277 (1991)
Facile syntheses of ribonucleoside 5'-triphosphates have been accomplished in good yield (>60percent) in a one-pot reaction of unprotected nucleosides with phosphoryl chloride followed by treatment of the resulting phosphorodichloridate with tri-n-butylammonium phosphate in the presence of dimethylformamide.
Supported Synthesis of Adenosine Nucleotides and Derivatives on a Benzene-Centered Tripodal Soluble Support
Appy, Lucie,Peyrottes, Suzanne,Roy, Béatrice
, (2021/06/23)
The first soluble-phase synthesis of adenosine nucleotides including α,β and β,γ-methylene bisphosphonate analogues on a multi-pod support is reported. Anchoring of a 2’,3’-protected purine nucleoside to the tripodal support via the nucleobase was successfully achieved using a microwave assisted Cu(I)-catalyzed azide-alkyne cycloaddition. Then, phosphorylation was performed, followed by cleavage with aqueous ammonia to provide adenine derivatives, and finally deprotection. When using benzylamine instead of ammonia, a derivative with N6-benzylamine adenine as nucleobase was obtained. This methodology allows to access adenosine 5’-mono, di and triphosphates, as well as various analogues of pharmacological interest in modest to good yields.
A Modular Synthesis of Modified Phosphoanhydrides
Hofer, Alexandre,Cremosnik, Gregor S.,Müller, Andr C.,Giambruno, Roberto,Trefzer, Claudia,Superti-Furga, Giulio,Bennett, Keiryn L.,Jessen, Henning J.
, p. 10116 - 10122 (2015/07/07)
Phosphoanhydrides (P-anhydrides) are ubiquitously occurring modifications in nature. Nucleotides and their conjugates, for example, are among the most important building blocks and signaling molecules in cell biology. To study and manipulate their biological functions, a diverse range of analogues have been developed. Phosphate-modified analogues have been successfully applied to study proteins that depend on these abundant cellular building blocks, but very often both the preparation and purification of these molecules are challenging. This study discloses a general access to P-anhydrides, including different nucleotide probes, that greatly facilitates their preparation and isolation. The convenient and scalable synthesis of, for example, 18O labeled nucleoside triphosphates holds promise for future applications in phosphoproteomics. Building the building blocks: This study discloses a general method for the functionalization of unprotected nucleotides and sugar phosphates with P-amidites in a highly modular way. The strategy facilitates the preparation of thiophosphate-containing nucleotides, 18O-labeled nucleoside triphosphates, and farnesylated nucleotides, as well as a range of dinucleoside polyphosphates and nucleotide sugars.