Automated solid-phase synthesis of RNA oligonucleotides containing a nonbridging phosphorodithioate linkage via phosphorothioamidites.
This work describes a general method for the synthesis of oligoribonucleotides containing a site-specific nonbridging phosphorodithioate linkage via automated solid-phase synthesis using 5'-O-DMTr-2'-O-TBS-ribonucleoside 3'-N,N-dimethyl-S-(2,4-dichlorobenzyl) phosphorothioamidites (2a-2d). The 3'-phosphorothioamidites (2a-2d) can be conveniently prepared in good yields (86-99%) via a one-pot reaction from the corresponding 5'-O-DMTr-2'-O-TBS-ribonucleosides (1a-1d).
Department of Biochemistry & Molecular Biology, The University of Chicago, 929 East 57th Street, Chicago, Illinois 60637, United States. nli@uchicago.edu
Nan-Sheng
NS
Li
John K
JK
Frederiksen
Joseph A
JA
Piccirilli
D001483:Base Sequence; D015394:Molecular Structure; D009841:Oligonucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D009943:Organophosphorus Compounds / Q000737:chemistry*; D009946:Organothiophosphorus Compounds / Q000737:chemistry*; D010710:Phosphates / Q000737:chemistry*; D012313:RNA / Q000138:chemical synthesis* / Q000737:chemistry; D012263:Ribonucleosides / Q000737:chemistry*; D060327:Solid-Phase Synthesis Techniques
D009841:Oligonucleotides; D009943:Organophosphorus Compounds; D009946:Organothiophosphorus Compounds; D010710:Phosphates; D012263:Ribonucleosides; C434331:phosphoramidite; D012313:RNA; C083120:phosphorodithioic acid