New photoacids in microarray synthesis of oligonucleotides

Abstract

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.

Keywords

• Microchip synthesizer of oligonucleotides
• Oxime sulfonate
• Photoacid generator
• Trityl cation
• Oligonucleotide