Synthesis and Characterisation of Photolabile SPhNPPOC-Protected (R)-MiniPEG Containing Chiral γ-Peptide Nucleic Acid Monomers
Qingteng Lai A , Bo Dong A B , Kaixuan Nie A B , Huanhuan Shi A B , Bo Liang C and Zhengchun Liu
A B D
A Hunan Key Laboratory for Super Microstructure and Ultrafast Process, Department of Electronic Information Science and Technology, School of Physics and Electronics, Central South University, Changsha, Hunan 410083, China.
B School of Basic Medical Science, Central South University, Changsha, Hunan 410083, China.
C State Engineering Laboratory of Highway Maintenance Technology, School of Traffic and Transportation Engineering, Changsha University of Science and Technology, Changsha, Hunan 410114, China.
D Corresponding author. Email: liuzhengchunseu@126.com
Australian Journal of Chemistry 74(3) 199-203 https://doi.org/10.1071/CH20017
Submitted: 16 January 2020 Accepted: 13 August 2020 Published: 9 September 2020
Abstract
Peptide nucleic acid (PNA) microarrays are expected to be developed as a new generation of gene detection tools. However, poor water solubility and the limitation of the sequence design of achiral PNA probes mainly hinder their application. Accordingly, (R)-diethylene glycol containing a chiral PNA (miniPEG-γPNA) has been developed to solve these problems. Light-directed synthesis is an effective method to fabricate high-density microarrays. Thiophenyl-2-(2-nitrophenyl)propoxycarbonyl (SPhNPPOC) is a newly synthesised photolabile protective group with high photolytic efficiency. Protecting the PNA monomers with SPhNPPOC may improve the preparation process of PNA microarrays by light-directed synthesis in terms of shortening the deprotection time and restraining side reactions. In this article, SPhNPPOC/carbobenzoxy (Cbz)-protected chiral miniPEG-γPNA monomers are synthesised, and the photo-deprotection rate is approximately twice that of a 2-(2-nitrophenyl)propyloxycarbonyl (NPPOC)-protected monomer. The monomers are expected to be used for the efficient and rapid fabrication of chiral miniPEG-γPNA microarrays through a photolithographic strategy.
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