Open AccessPre−activation strategy for oligodeoxyribonudeotide synthesis using triaryloxydichloro−phosphoranes in the phosphotriester method
Author(s) -
Hitoshi Hotoda,
Takehiko Wada,
Mitsuo Sekine,
Tsujiaki Hata
Publication year - 1989
Publication title -
nucleic acids research
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 9.008
H-Index - 537
eISSN - 1362-4954
pISSN - 0305-1048
DOI - 10.1093/nar/17.13.5291
Subject(s) - reagent , tris , condensation , combinatorial chemistry , condensation reaction , inert , phosphate , nucleotide , chemical synthesis , biology , stereochemistry , organic chemistry , biochemistry , chemistry , catalysis , in vitro , physics , thermodynamics , gene
Triaryloxydichlorophosphoranes were tested as condensing agents for oligodeoxyribonucleotide synthesis in the phosphotriester method. Tris(2,4,6-tribromophenoxy)dichlorophosphorane (BDCP) was found to be a relatively stable crystalline material which could be used as a chemical reagent. A notable feature of the BDCP-promoted condensation reaction was studied by 31P-NMR. A small amount of BDCP compared to the conventional condensing agent was effective for the generation of active nucleotide intermediates and BDCP itself was quantitatively converted into an inert material, tris(2,4,6-tribromophenyl)phosphate (2). Thus, BDCP enabled us to separate the activation step from the condensation process in the phosphotriester method. This preactivation method was applied to the solid-phase synthesis.