Synthesis of the phosphoramidite derivatives of 2'-deoxy-2'-C-alpha-methylcytidine and 2'-deoxy-2'-C-alpha-hydroxymethylcytidine: analogues for chemical dissection of RNA's 2'-hydroxyl group.
Oligonucleotides containing 2'-C-alpha-methyl and 2'-C-alpha-hydroxymethyl modifications enable strategies for delineation of the distinctive role fulfilled by the 2'-hydroxyl group in RNA structure and function. Synthetic routes to the phosphoramidite derivatives of 2'-deoxy-2'-C-alpha-methylcytidine (14%, 15 steps) and 2'-deoxy-2'-C-alpha-hydroxymethylcytidine (19%, 10 steps) from methyl 3,5-di-O-(4-chlorobenzyl)-alpha-d-ribofuranoside are developed.
Li
Nan-Sheng
NS
Department of Biochemistry and Molecular Biology, University of Chicago, 5841 South Maryland Avenue, MC 1028, Chicago, Illinois 60637, USA.
Piccirilli
Joseph A
JA
D003562:Cytidine / Q000031:analogs & derivatives; D003841:Deoxycytidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D017665:Hydroxyl Radical / Q000737:chemistry; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D012313:RNA / Q000737:chemistry*; D014529:Uridine / Q000031:analogs & derivatives
D007202:Indicators and Reagents; D003841:Deoxycytidine; C055031:2'-methyl-2'-deoxycytidine; D017665:Hydroxyl Radical; D003562:Cytidine; D012313:RNA; D014529:Uridine