New photoacids in microarray synthesis of oligonucleotides

Photochemical activity of thiophene oxime esters and of sulfonium salt tris[4-(4-acetylphenyl)sulfanylphenyl]sulfonium tetrakis(2,3,4,5,6-pentafluorophenyl)boranuide (photoacid generator 290 [PAG 290]) was investigated in a reaction forming a trityl cation. Quantum yields of photoacid phototransform...

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Bibliographic Details
Published in:Journal of Saudi Chemical Society 2023-11, Vol.27 (6), p.101709, Article 101709
Main Authors: Sinyakov, A.N., Kostina, E.V., Zaytsev, D.E., Chukanov, N.V., Kamaev, G.N., Bessmeltsev, V.P., Shelkovnikov, V.V., Vasil'ev, E.V.
Format: Article
Language:English
Subjects:
Microchip synthesizer of oligonucleotides
Oligonucleotide
Oxime sulfonate
Photoacid generator
Trityl cation
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Summary:Photochemical activity of thiophene oxime esters and of sulfonium salt tris[4-(4-acetylphenyl)sulfanylphenyl]sulfonium tetrakis(2,3,4,5,6-pentafluorophenyl)boranuide (photoacid generator 290 [PAG 290]) was investigated in a reaction forming a trityl cation. Quantum yields of photoacid phototransformation reactions and of photodetritylation of 5′-O-(4,4′-dimethoxytrityl)thymidine were determined. Then, [(Z)-[(3Z)-3-[cyano(o-tolyl)methylene]-2-thienylidene]amino] 2,4,6-triisopropylbenzenesulfonate (H 365) and PAG 290 were used as detritylation photoactivators in a procedure of oligonucleotide synthesis on a microchip synthesizer prototype, and several oligonucleotides were synthesized. At the stage of oligonucleotide chain extension, the yield was 94–96%. The tested photoacids can be successfully applied to microchip synthesis of oligonucleotides.
ISSN:1319-6103
DOI:10.1016/j.jscs.2023.101709