title: Synthesis and application of a new phosphorylating agent: S-(N-monomethoxytritylaminoethyl)-O-(o-chlorophenyl)phosphorothi oate.
abstract: A new phosphorylating agent, S-(N-monomethoxytritylaminoethyl)-O-(O-chlorophenyl) phosphorothioate, was prepared and reacted with a 5'-hydroxyl group of an oligonucleotide using 1-mesitylene-sulfonyl-3-nitrotriazole (MSNT) as a condensing agent. After base labile protecting groups were removed, the partially deprotected oligonucleotide was separated on a reversed phase column and converted to the oligonucleotide with an aminoethyl or a phosphoryl group at the 5'-end by treatment with 80% acetic acid or iodine-water, respectively. The syntheses of ppT, pppT, A5'pp5'T and A5'ppp5'T were also performed by treatment of 5'-O-(N-monomethoxytritylaminoethylthiophosphoryl) thymidine with tri-n-octylammonium salt of phosphoric acid, pyrophosphoric acid, pA and ppA, respectively.
authors.affiliation: Faculty of Pharmaceutical Sciences, Osaka University, Japan.
authors.forename: T
authors.initials: T
authors.lastname: Tanaka
authors.forename: Y
authors.initials: Y
authors.lastname: Yamada
authors.forename: T
authors.initials: T
authors.lastname: Sakata
authors.forename: S
authors.initials: S
authors.lastname: Uesugi
authors.forename: M
authors.initials: M
authors.lastname: Ikehara
mesh_terms: D007202:Indicators and Reagents; D009841:Oligonucleotides / Q000138:chemical synthesis*; D009946:Organothiophosphorus Compounds / Q000138:chemical synthesis*; D010766:Phosphorylation; D013329:Structure-Activity Relationship
chemical_list: D007202:Indicators and Reagents; D009841:Oligonucleotides; D009946:Organothiophosphorus Compounds; C058618:S-(N-monomethoxytritylaminoethyl)-O-(2-chlorophenyl)phosphorothioate