Collect. Czech. Chem. Commun. 2006, 71, 929-955

Hydroxyproline-Based DNA Mimics: A Review on Synthesis and Properties

Vladimir A. Efimov* and Oksana G. Chakhmakhcheva

Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, ul. Miklukho-Maklaya 16/10, Moscow 117997, Russia


With the aim to improve physicochemical and biological properties of natural oligonucleotides, many types of DNA analogues and mimics are designed on the basis of hydroxyproline and its derivatives, and their properties are evaluated. Among them, two types of DNA mimics representing hetero-oligomers constructed from alternating monomers of phosphono peptide nucleic acids and monomers on the base of trans-1-acetyl-4-hydroxy-L-proline (HypNA-pPNAs) and oligomers constructed from monomers containing (2S,4R)-1-acetyl-4-hydroxypyrrolidine-2-phosphonic acid backbone (pHypNAs) are of particular interest. In a set of in vitro and in vivo assays, it was shown that HypNA-pPNAs and pHypNAs demonstrated a high potential for the use in nucleic acid based diagnostics, isolation of nucleic acids and antisense experiments. A review with 53 references.

Keywords: PNA; DNA analogues; Phosphono-hydroxyproline; Hybridization; Inhibition of gene expression; Antisense oligonucleotides; Pyrrolidines; Backbone modified oligonucleotides.

References: 54 live references.