화학공학소재연구정보센터
Journal of the American Chemical Society, Vol.141, No.38, 15013-15017, 2019
Synthesis of Modified Nucleoside Oligophosphates Simplified: Fast, Pure, and Protecting Group Free
Phosphoramidite analogues of modified cyclotriphosphates provide a general and step-economical synthesis of nucleoside triphosphates and analogues on scale without the need for protecting groups. These reagents enable rapid access to pure nucleoside oligophosphates and a range of other analogues that were previously difficult to obtain (e.g., NH, CH2, CCl2, and CF2, replacements for O, phosphono- and phosphoimidazolides, -morpholidates, -azidates, and -fluoridates). DFT calculations demonstrate that the selectivity of the cyclotriphosphate opening reactions proceeds via an inline substitution mechanism that displaces the least charged leaving group.