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1,1,1,3,3,3-Hexafluoro-2-propyl group as a new phosphate protecting group for oligoribonucleotide synthesis in the phosphotriester approach

✍ Scribed by Shunichi Yamakage; Masayo Fujii; Hiroshi Takaku; Masaru Uemura

Publisher: Elsevier Science
Year: 1989
Tongue: French
Weight: 508 KB
Volume: 45
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(01)89492-8

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✦ Synopsis

The 1,1,1,3,3,3-Hexafluoro-2-propyl group can be used as a new class of phosphate protecting group for the protecting group of internucleotidic bonds in the oligonucleotide synthesis by the phosphotriester approach . This protecting group is removed easily by treatment with 0 .3 M N 1 ,N 1 ,N 3 ,N''-tetramethylguanidinium syn-2-pyridinealdoximate in pyridine-water (9 :1, v/v) .

The butylthiocarbonyl group was chosen for the protecting group of the 0 6 -amide and N 2 -amino functions of guanosine and the N 3imide group of uridine .

The fully protected monomer unit (10) was prepared by the reaction of the phosphorylating agent (1) with 7a . These monomer units have successfully been utilized for the synthesis of UGUCGGUC, the box 9R sequence of r-RNA precursor of Tetrahymena .

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