New acid photogenerators based on thioxanthen-9-one sulfonium derivatives for detritylation in the oligonucleotide synthesis

New acid photogenerators based on thioxanthen-9-one sulfonium derivatives for detritylation in the oligonucleotide synthesis Full article

Journal

Russian Chemical Bulletin
ISSN: 1066-5285 , E-ISSN: 1573-9171

Output data

Year: 2011, Volume: 60, Number: 3, Pages: 561-569 Pages count : DOI: 10.1007/s11172-011-0087-x

Tags

photoactivators of detritylation; acid photogenerators; trityl cation; thioxan-thenone derivatives

Authors

Shelkovnikov V. V. ¹ , Loskutov V. A. ¹ , Vasil'ev E. V. ^1,2 , Shekleina N. V. ¹ , Ryabinin V. A. ³ , Sinyakov A. N. ³

Affiliations

1	(Данные Web of science) Russian Acad Sci, Siberian Branch, NN Vorozhtsov Novosibirsk Inst Organ Chem, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, Res Educ Ctr Mol Design & Environm Safe Technol, Novosibirsk 630090, Russia
3	(Данные Web of science) Russian Acad Sci, Siberian Branch, Inst Chem Biol & Fundamental Med, Novosibirsk 630090, Russia

Photochemical activity of a number of cationic thioxanthen-9-one derivatives for the formation of the trityl cation was studied, which resulted in the selection of compounds suitable for photodetritylation. 10-(4-Heptyloxyphenyl)-9-oxo-2-(N,N,N-triethylammonio)methyl-9H-thioxanthenium bis(hexafluorophosphate) and 2-methyl-, 2-(2-methyl-1-propanoyl-2-tosyl)-, 1-chloro-4-propoxy-, and 2,4-diethyl-10-(4-heptyloxyphenyl)-9-oxo-9H-thioxanthenium hexafluorophosphates were found to be photoactivators of detritylation of 5'-O-(4,4'-dimethoxytrityl)thymidine. The detritylation reaction is the most efficient in dichloromethane. 2,4-Diethyl-10-(4-heptyloxyphenyl)-9-oxo-9H-thioxanthenium hexafluorophosphate was used as a detritylation photoactivator in the oligonucleotide synthesis using an automated DNA synthesizer. The yield in the elongation step of the oligonucleotide chain was 98%.

Shelkovnikov V.V. , Loskutov V.A. , Vasil'ev E.V. , Shekleina N.V. , Ryabinin V.A. , Sinyakov A.N.
New acid photogenerators based on thioxanthen-9-one sulfonium derivatives for detritylation in the oligonucleotide synthesis
Russian Chemical Bulletin. 2011. V.60. N3. P.561-569. DOI: 10.1007/s11172-011-0087-x WOS Scopus РИНЦ OpenAlex

Published print:	Mar 1, 2011
Published online:	Sep 6, 2011

Web of science:	WOS:000294715900026
Scopus:	2-s2.0-80052703506
Elibrary:	18005086
OpenAlex:	W2011518617

DB	Citing
Web of science	8
Scopus	9
Elibrary	10
OpenAlex	11