Fine-Tuning of Acid Susceptibility of 4, 4 ’ -Dimethoxytrityl Ether Derivatives by a Methoxy Group Introduced via a Styryl Substituent

Kohji      Seio; Takahide      Sasaki; Mitsuo      Sekine

doi:10.2174/1570178043488428

Abstract

To overcome the problem of depurination in oligoDNA synthesis, we tried to fine-tune the acid lability of the DMTr group by adding a substituted styryl group on the phenyl ring. The styryl groups could buffer the electron donating nature of the methoxy group and enabled the fine-tuning of the acid lability.

Keywords: protecting group, trityl group, oligodeoxynucleotide synthesis, depurination

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Letters in Organic Chemistry

Title: Fine-Tuning of Acid Susceptibility of 4, 4 ’ -Dimethoxytrityl Ether Derivatives by a Methoxy Group Introduced via a Styryl Substituent

Volume: 1 Issue: 2

Author(s): Kohji Seio, Takahide Sasaki and Mitsuo Sekine

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Keywords: protecting group, trityl group, oligodeoxynucleotide synthesis, depurination

Abstract: To overcome the problem of depurination in oligoDNA synthesis, we tried to fine-tune the acid lability of the DMTr group by adding a substituted styryl group on the phenyl ring. The styryl groups could buffer the electron donating nature of the methoxy group and enabled the fine-tuning of the acid lability.

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Seio Kohji, Sasaki Takahide and Sekine Mitsuo, Fine-Tuning of Acid Susceptibility of 4, 4 ’ -Dimethoxytrityl Ether Derivatives by a Methoxy Group Introduced via a Styryl Substituent, Letters in Organic Chemistry 2004; 1 (2) . https://dx.doi.org/10.2174/1570178043488428