54925-71-2Relevant academic research and scientific papers
Synthesis and antibacterial activity of 5′-tetrachlorophthalimido and 5′-azido 5′-deoxyribonucleosides
Van Ostrand, Robert,Jacobsen, Casey,Delahunty, Alicia,Stringer, Carley,Noorbehesht, Ryan,Ahmed, Haidi,Awad, Ahmed M.
, p. 181 - 197 (2017/02/15)
Reported is an efficient synthesis of adenyl and uridyl 5′-tetrachlorophthalimido-5′-deoxyribonucleosides, and guanylyl 5′-azido-5′-deoxyribonucleosides, which are useful in solid-phase synthesis of phosphoramidate and ribonucleic guanidine oligonucleotides. Replacement of 5′-hydroxyl with tetrachlorophthalimido group was performed via Mitsunobu reaction for adenosine and uridine. An alternative method was applied for guanosine which replaced the 5′-hydroxyl with an azido group. The resulting compounds were converted to 5′-amino-5′-deoxyribonucleosides for oligonucleotide synthesis. Synthetic intermediates were tested as antimicrobials against six bacterial strains. All analogs containing the 2′,3′-O-isopropylidine protecting group demonstrated antibacterial activity against Neisseria meningitidis, and among those analogs with 5′-tetrachlorophthalimido and 5′-azido demonstrated increased antibacterial effect.
RNA synthesis via dimer and trimer phosphoramidite block coupling
Hassler, Matthew,Wu, Yi Qiao,Mallikarjuna Reddy,Chan, Tak Hang,Damha, Masad J.
supporting information; experimental part, p. 2575 - 2578 (2011/06/21)
The solid-phase synthesis of oligoribonucleotides using dimer and trimer phosphoramidite blocks is described. This method significantly reduces the total number of steps required in the synthesis of a target RNA sequence, provides more material, and simpl
Synthesis of cyclic di-nucleotidic acids as potential inhibitors targeting diguanylate cyclase
Ching, Shi Min,Tan, Wan Jun,Chua, Kim Lee,Lam, Yulin
experimental part, p. 6657 - 6665 (2010/10/21)
Five analogs of cyclic di-nucleotidic acid including c-di-GMP were synthesized and evaluated for their biological activities on Slr1143, a diguanylate cyclase of Synechocystis sp. Slr1143 was overexpressed from the recombinant plasmid which contained the gene of interest and subsequently purified by affinity chromatography. A new HPLC method capable of separating the compound and product peaks with good resolution was optimized and applied to the analysis of the compounds. Results obtained show that cyclic di-inosinylic acid 1b demonstrates a stronger inhibition on Slr1143 than c-di-GMP and is a potential inhibitor for biofilm formation.
Synthesis of 2'-O-substituted ribonucleosides.
Serebryany,Beigelman
, p. 1007 - 1009 (2007/10/03)
An efficient synthesis of 2'-O-substituted ribonucleosides, including 2'-O-TBDMS and 2'-O-TOM protected as well as 2'-O-Me and 2'-O-allyl derivatives is presented. Di-t-butylsilylene group was employed for simultaneous protection of 3'- and 5'- hydroxyl functions of nucleoside on the first step. Subsequent silylation or alkylation of free 2'-OH followed by introduction of suitable protection on the base moiety and removal of cyclic silyl protection gave target compounds in a high yield.
Aqueous trichloroacetic acid: Another useful reagent for highly selective 5′-desilylation of multisilylated nucleosides
Zhu, Xue-Feng,Williams, Howard J.,Scott, A. Ian
, p. 2011 - 2016 (2007/10/03)
Highly selective 5′-desilylation of multisilylated nucleosides can be achieved in excellent yield by treatment with 4.2 M aqueous trichloroacetic acid:THF (1:4) at 0°C.
An efficient preparation of protected ribonucleosides for phosphoramidite RNA synthesis
Serebryany, Vladimir,Beigelman, Leonid
, p. 1983 - 1985 (2007/10/03)
An efficient synthesis of protected ribonucleosides useful for phosphoramidite RNA synthesis is described. Di-t-butylsilylene group was employed for simultaneous protection of 3′- and 5′-hydroxyl functions of nucleoside. Subsequent silylation of free 2′-O
Ceric ammonium nitrate on silica gel for efficient and selective removal of trityl and silyl groups
Hwu, Jih Ru,Jain, Moti L.,Tsai, Fu-Yuan,Tsay, Shwu-Chen,Balakumar, Arumugham,Hakimelahi, Gholam H.
, p. 5077 - 5088 (2007/10/03)
Silicna gel-supported ceric ammonium nitrate (CAN-SiO2) was found effective for rapid and selective cleavage of trityl (Tr), monomethoxytrityl (MMTr), and dimethoxytrityl (DMTr) groups from protected nucleosides and nucleotides under mild conditions. Efficiency of deprotections depended upon the stability of th resultant carbocationic species: DMTr+ > MMTr+ > Tr+. Use of a catalytic amount of this solid-supported reagent can also efficiently and selectively remove the tert butyldimethylsilyl or the triisopropylsilyl group from a primary hydroxyl functionality in di- or trisilyl ethers of ribonucleosides. A comparative stud of deprotection reactions by utilization of CAN alone or CAN-SiO2 indicates a remarkable increase in the rate of the reactions involving a solid support. The mechanism of electron-transfer processes is proposed for the use of CAN-SiO2 in the removal of these protective groups from organic molecules.
Facile and highly selective 5′-desilylation of multisilylated nucleosides
Zhu, Xue-Feng,Williams, Howard J.,Ian Scott
, p. 2305 - 2306 (2007/10/03)
The facile and highly selective 5′-desilylation of multisilylated nucleosides was discussed. The selective 5′-desilylation using aqueous acetic acid can be improved if THF is added as a co-solvent. It was found that the use of THF increases the solubility
Removal of TBDMS protecting groups from carbohydrates using catalytic transfer hydrogenation
Cormier
, p. 187 - 188 (2007/10/02)
Catalytic transfer hydrogenation provides a simple and convenient method for the cleavage of TBDMS ethers from both primary and secondary hydroxyl groups.
ISOMERIZATION OF tert-BUTYLDIMETHYLSILYL PROTECTING GROUPS IN RIBONUCLEOSIDES
Ogilvie, Kelvin K.,Entwistle, Douglas W.
, p. 203 - 210 (2007/10/02)
The tert-butyldimethylsilyl group undergoes isomerization between O-2' and O-3' in ribonucleosides in solution.Isomerization is most rapid in protic solvents and extremely slow in such solvents as dry dimethyl sulfoxide, pyridine, oxolane, chloroform, or
