β,γ-Bis-substituted PNA with configurational and conformational switch: preferred binding to cDNA/RNA and cell-uptake studies†,10.1039/C5CC00891C

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β,γ-Bis-substituted PNA with configurational and conformational switch: preferred binding to cDNA/RNA and cell-uptake studies†

Tanaya Bose,Anjan Banerjee,Smita Nahar,Souvik Maiti,Vaijayanti A. Kumar

Chemical Communications Pub Date : 03/25/2015 00:00:00 , DOI:10.1039/C5CC00891C

Abstract

(S,S)- and (R,R)-β,γ-Bis-substituted PNAs were synthesized from the C-2 symmetric vicinal diamine system embedded in 1,4 dihydroxybutane and 1,4-dimethoxybutane scaffolds. (R,R)-β,γ-Bis-methoxymethyl-PNA derived from D-tartaric acid was found to be in the right configuration and conformation to be an excellent mimic of PNA, endowed with superior ability to enter into cells.