40733-27-5Relevant articles and documents
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.
Characterization of a 5′-aldehyde terminus resulting from the oxidative attack at C5′ of a 2-deoxyribose on DNA
Angeloff,Dubey,Pratviel,Bernadou,Meunier
, p. 1413 - 1420 (2007/10/03)
The 5′-aldehyde terminus is a DNA oxidative damage resulting from attack at C5′ of 2-deoxyriboses by some potent natural or chemical DNA cleavers. To offer a fast and specific method for characterization of this type of damage, we used on-line electrospray ionization mass spectrometry (ESI-MS) detection during liquid chromatography analyses. The intrinsic reactivity of 5′-aldehyde terminus with nucleophiles (formation of hydrate with water, of a Tris adduct with Tris buffer) or through β-elimination reaction resulted in complex LC profiles and MS data. We showed that derivatization of the aldehyde function as an oxime ether gives a stable derivative easy to characterize during on-line ESI-MS analyses. Complete structural characterization of the Tris adduct and the oxime ether derivative were obtained from MS and detailed NMR studies performed on derivatized 5′-aldehyde thymidine models.