14522-18-0Relevant academic research and scientific papers
First synthesis of enantio-uracil dinucleotide, comparison of physicochemical properties of their enantiomers, and separation by chiral column chromatography
Miyashita, Takanori,Sakata, Shinji,Hayakawa, Hiroyuki
, p. 8605 - 8607 (2003)
Enantio-uracil dinucleotide 5, which consists of two L-uridylic acids and one pyrophosphate, was synthesized for the first time in our laboratory. Benzolyated L-uridine was prepared by a stereoselective glycosylation of silylated uracil with L-1-O-acetyl-2,3,5-tri-O-benzoylribose (L-ABR 7). After deprotection, L-uridine 9 was converted to P1,P4-di(L- uridine 5′-) tetraphosphate tetrasodium salt (L-UP4U 5) by treatment of L-UMP morpholidate 10c with triethylammonium pyrophosphate (TEA-PPi 11b). Spectral data of synthesized L-UP4U 5 are given in the references. All spectral data were identical with those of UP4U 3 except the specific rotation, which showed a positive value compared to UP4U 3 having a negative value. Furthermore, the separation by chiral column chromatography was investigated.
A nucleotide dimer synthesis without protecting groups using montmorillonite as catalyst
Joshi, Prakash C.,Aldersley, Michael F.,Zagorevskii, Dmitri V.,Ferris, James P.
experimental part, p. 536 - 566 (2012/10/08)
A synthesis has been developed providing nucleotide dimers comprising natural or unnatural nucleoside residues. A ribonucleoside 5-phosphorimidazolide is added to a nucleoside adsorbed on montmorillonite at neutral pH with the absence of protecting groups. Approximately 30% of the imidazolide is converted into each 2-5 dimer and 3-5 dimer with the rest hydrolyzed to the 5-monophosphate. Experiments with many combinations have suggested the limits to which this method may be applied, including heterochiral and chimeric syntheses. This greener chemistry has enabled the synthesis of dimers from activated nucleotides themselves, activated nucleotides with nucleosides, and activated nucleotides with nucleotide 5-monophosphates.
