Watson-Crick base-pairing properties of nucleic acid analogues with stereocontrolled α and β torsion angles (α,β-D-CNAs)

Abstract

(Chemical Equation Presented) Constrained nucleic acids (α,β-D-CNAs) have an ethylene bridge that locks the α and β backbone torsion angles of DNA in the canonical (gauche(-),trans) conformation, as in B-form DNA (see picture), or in the noncanonical (gauche(+),trans) conformation. Canonical α,β-D-CNAs enhance the duplex-forming ability of oligonucleotides with complementary DNA, while noncanonical α,β-D-CNAs stabilize distorted B-DNA structures. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.