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

Org Biomol Chem. 2014 Jul 28;12(28):5089-93. doi: 10.1039/c4ob00418c.

Authors

Takayoshi Watanabe¹, Tomoko Hoshida, Jun Sakyo, Mariko Kishi, Satoshi Tanabe, Junichi Matsuura, Shingo Akiyama, Makiko Nakata, Yasuaki Tanabe, Akinobu Z Suzuki, Soichiro Watanabe, Toshiaki Furuta

Affiliation

¹ Department of Biomolecular Science, Faculty of Science, Toho University, 2-2-1 Miyama, Funabashi, Chiba 274-8510, Japan. furuta@biomol.sci.toho-u.ac.jp.

PMID: 24921960
DOI: 10.1039/c4ob00418c

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Coumarins / chemistry*
Electrophoresis, Agar Gel
Light
Peptide Nucleic Acids / chemical synthesis*
Peptide Nucleic Acids / chemistry
Photolysis
Polymerase Chain Reaction
Pyrimidines / chemistry*

Substances

Coumarins
Peptide Nucleic Acids
Pyrimidines