79974-68-8Relevant academic research and scientific papers
Synthesis of triazole-linked SAM-adenosine conjugates: Functionalization of adenosine at N-1 or N-6 position without protecting groups
Atdjian, Colette,Braud, Emmanuelle,Coelho, Dylan,Ethève-Quelquejeu, Mélanie,Iannazzo, Laura
, (2020/08/07)
More than 150 RNA chemical modifications have been identified to date. Among them, methylation of adenosine at the N-6 position (m6A) is crucial for RNA metabolism, stability and other important biological events. In particular, this is the most abundant
A Practical Method for Regioselective 5′-O-tert-Butyldimethylsilyl Deprotection of Persilylated Nucleosides by Methanolic Phosphomolybdic Acid
Huang, Hua-Shan,Kong, Rui,Zheng, Xiu-An,Chen, Wei-Jie,Han, Shuai-Bo,Zeng, De-Yun,Gong, Shan-Shan,Sun, Qi
supporting information, p. 2437 - 2443 (2018/11/23)
In nucleoside/nucleotide chemistry, the regioselective cleavage of 5′-O-TBS groups of persilylated nucleosides is a desired approach for structural functionalization at the 5′-position. However, efficient and practical methods for this purpose are still limited. In our research, we found that homogeneous methanolic phosphomolybdic acid (PMA) efficiently catalyzes the regioselective deprotection of 5′- O -TBS groups of a diversity of persilylated nucleoside substrates and can be applied in practical synthesis at scales of up to 15 g. 31 P NMR results indicated that an anion cluster forms and the Lewis acidity of homogeneous PMA is organic-solvent dependent. The efficacy and pronounced regioselectivity of methanolic PMA occurs as a result of a lowering of the Lewis acid strength upon solvation of the molybdophosphate anions.
Synthesis of Dimeric ADP-Ribose and Its Structure with Human Poly(ADP-ribose) Glycohydrolase
Lambrecht, Michael J.,Brichacek, Matthew,Barkauskaite, Eva,Ariza, Antonio,Ahel, Ivan,Hergenrother, Paul J.
supporting information, p. 3558 - 3564 (2015/03/30)
Poly(ADP-ribosyl)ation is a common post-translational modification that mediates a wide variety of cellular processes including DNA damage repair, chromatin regulation, transcription, and apoptosis. The difficulty associated with accessing poly(ADP-ribose) (PAR) in a homogeneous form has been an impediment to understanding the interactions of PAR with poly(ADP-ribose) glycohydrolase (PARG) and other binding proteins. Here we describe the chemical synthesis of the ADP-ribose dimer, and we use this compound to obtain the first human PARG substrate-enzyme cocrystal structure. Chemical synthesis of PAR is an attractive alternative to traditional enzymatic synthesis and fractionation, allowing access to products such as dimeric ADP-ribose, which has been detected but never isolated from natural sources. Additionally, we describe the synthesis of an alkynylated dimer and demonstrate that this compound can be used to synthesize PAR probes including biotin and fluorophore-labeled compounds. The fluorescently labeled ADP-ribose dimer was then utilized in a general fluorescence polarization-based PAR-protein binding assay. Finally, we use intermediates of our synthesis to access various PAR fragments, and evaluation of these compounds as substrates for PARG reveals the minimal features for substrate recognition and enzymatic cleavage. Homogeneous PAR oligomers and unnatural variants produced from chemical synthesis will allow for further detailed structural and biochemical studies on the interaction of PAR with its many protein binding partners. (Chemical Equation Presented).
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.
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
Nucleosides, XXXVII. - Synthesis and Properties of 2'-O- and 3'-O-(tert-Butyldimethylsilyl)-5'-O-(4-methoxytrityl)- and 2',3'-Bis(O-tert-butyldimethylsilyl)ribonucleosides - Starting Materials for Oligoribonucleotide Syntheses
Flockerzi, Dieter,Silber, Gunter,Charubala, Ramamurthy,Schlosser, Wilhelm,Varma, Rajendra Singh,et al.
, p. 1568 - 1585 (2007/10/02)
The synthesis of aminoacylated 5'-O-(4-methoxytrityl)ribonucleosides of adenosine (1), guanosine (9), cytidine (31), uridine (17), and 5,6-dihydrouridine (23) have been optimized and these compounds (4, 12, 33, 18 and 24) silylated by tert-butyldimethylsilyl chloride.The corresponding 2'- and 3'-mono-O- as well as 2',3'-bis-O-(tert-butyldimethylsilyl) derivatives have been isolated by combination of chromatographical methods and fractional crystallization procedures in preparative scale.The characterization of the newly synthesized compounds was achieved by UV and 13C-NMR spectra.
