Synthesis of nucleobase-caged peptide nucleic acids having improved photochemical properties

Takayoshi Watanabe; Tomoko Hoshida; Jun Sakyo; Mariko Kishi; Satoshi Tanabe; Junichi Matsuura; Shingo Akiyama; Makiko Nakata; Yasuaki Tanabe; Akinobu Z. Suzuki; Soichiro Watanabe; Toshiaki Furuta

doi:10.1039/C4OB00418C

Synthesis of nucleobase-caged peptide nucleic acids having improved photochemical properties†

Takayoshi Watanabe,‡^a Tomoko Hoshida,^a Jun Sakyo,^a Mariko Kishi,^a Satoshi Tanabe,^a Junichi Matsuura,^a Shingo Akiyama,^a Makiko Nakata,^a Yasuaki Tanabe,^a Akinobu Z. Suzuki,^a Soichiro Watanabe^a and Toshiaki Furuta*^a

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^a Department of Biomolecular Science, Faculty of Science, Toho University, 2-2-1 Miyama, Funabashi, Chiba 274-8510, Japan
E-mail: furuta@biomol.sci.toho-u.ac.jp
Fax: +81-47-472-1169
Tel: +81-47-472-1169

Abstract

A nucleobase-caged peptide nucleic acid (PNA) having a (6-bromo-7-methoxycoumarin)-4-ylmethoxycarbonyl (Bmcmoc) caging group was newly synthesized. The Bmcmoc-caged PNAs were photolyzed to produce parent PNAs with a high photochemical efficiency. Introduction of a single Bmcmoc group was sufficient to suppress polymerase chain reaction (PCR) clamping activity and triplex invasion complex formation. Photo-mediated restoration of the PCR clamping activity was also demonstrated.

Organic & Biomolecular Chemistry

Synthesis of nucleobase-caged peptide nucleic acids having improved photochemical properties†

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Synthesis of nucleobase-caged peptide nucleic acids having improved photochemical properties

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