Synthesis of DNA-Binding Peptoids

Abstract

Programmable molecular recognition through nucleic acid base pairing has enabled applications in nano- and biotechnology using DNA, RNA, PNA, and more recently, bifacial PNA (bPNA). We describe herein the synthesis and DNA recognition properties of peptoid backbones bearing the bifacial synthetic nucleobase melamine. These ‘peptoid nucleic acids’ hybridize with thymine-rich DNA, like their peptide cognate (bPNA). DNA complexation is highly sensitive to peptoid side-chain length and overall charge. Peptoids isomeric with peptide bPNA were less efficient at DNA recognition, possibly due to conformational and steric differences.

1 Triazines and DNA Molecular Recognition

2 Synthesis of DNA-Binding Peptoids

3 Peptoid–DNA Binding Studies

Key words

triazine - cyanuric chloride - peptide synthesis - assembly - PNA - peptoids

• References and Notes

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