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  APPLICATIONS OF PEPTIDES NUCLEIC ACIDS (PNA) IN MOLECULAR MEDICINE AND BIOTECHNOLOGYFREEfree


Minerva Biotecnologica 1999 September;11(3):163-74

Copyright © 1999 EDIZIONI MINERVA MEDICA

language: English

The chemistry of peptide nucleic acids

Sforza S., Corradini R., Galaverna G., Dossena A., Marchelli R.

Dipartimento di Chimica Organica ed Industriale, Università degli Studi, Parma, Italy


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Pep­tide ­Nucleic ­Acids (PNA) are oli­go­nu­cleo­tide ana­logues in ­which the ­sugar-phos­phate back­bone has ­been ­replaced by a poly­amidic ­chain. ­They ­were ­shown to ­bind to com­ple­men­tary DNA and RNA ­sequences ­with ­high ­affinity and selec­tivity. For ­these rea­sons, ­they ­have ­become ­very ­popular, as ­tools in molec­ular ­biology and bio­tech­nology, as diag­nostic ­agents, and as poten­tial anti­sense ­drugs. The syn­thesis of PNA ­monomers has ­been ­described ­with dif­ferent strat­e­gies ­using dif­ferent pro­tecting ­groups for the ­amino func­tion (Boc, ­Fmoc, or Mmt) and for the nucle­obases. Strat­e­gies for olig­om­er­iza­tion, ­either by homo­ge­neous or by ­solid-­phase syn­thesis, ­have ­been ­reported. A ­large ­number of mod­i­fied PNAs ­have ­also ­been envis­aged. The ­present ­work pro­vides a gen­eral over­view of the dif­ferent PNA back­bones and of mod­i­fied nucle­obases, ­with spe­cial ­regard to the syn­thetic strat­e­gies ­used. The occur­rence of racem­iza­tion ­during the syn­thesis of ­chiral PNA ana­logues is ­also dis­cussed. PNA/DNA ­duplexes are ­formed ­obeying the ­usual ­Watson-­Crick ­rules, as ­well as (PNA)2/ DNA trip­lexes ­with homo­py­rim­i­dine ­PNAs in low ­ionic ­strength solu­tions. The ­thermal ­stability of ­these ­adducts is ­described. In par­tic­ular, the influ­ence of PNA struc­ture mod­ifi­ca­tion and chi­rality on the ­binding ­affinity and selec­tivity are dis­cussed.

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