New synthetic route to gamma-mercaptomethyl PNA monomers

New synthetic route to gamma-mercaptomethyl PNA monomers (258 visite)

Pensato S, D'Andrea LD, Pedone C, Romanelli A

Synth Commun Synthetic Communications (ISSN: 0039-7911), 2008; 38(15): 2499-2506.

Tipo di articolo: Journal Article,

Impact factor: 0.981, Impact factor a 5 anni: 1.018

Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-51349136658&partnerID=40&md5=6409508e1c8c38eb82b006b590d21263

Parole chiave: Amino Acid, Pna, Synthesis, Gamma Mercaptomethyl Peptide Nucleic Acid, Unclassified Drug, Amino Terminal Sequence, Article, Biosensor, Dna Determination, Microarray Analysis, Quantum Yield,

Affiliazioni:

*** IBB - CNR ***
University of Naples Federico II, Department of Biological Science, School of Biotechnological Sciences, Napoli, Italy
CNR, Institute of Biostructure and Bioimaging, Napoli, Italy

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Peptide nucleic acids (PNAs) are oligonucleotide mimics widely used as antisense, antigene molecules, and biotechnological tools. Recently, several microarrays and other biosensors based on PNAs have been developed. The construction of PNA molecular beacons or light-up probes for DNA detection requires the labelling of the PNA moiety. Labels are usually attached at the C or N terminal end by a flexible linker or in the middle of a PNA sequence, substituting one PNA base with an artificial base or by attaching fluorophores to a modified PNA backbone. The need to develop simple protocols to label PNAs encouraged us to design a new procedure for the synthesis of γ-mercaptomethyl-modified PNA. Here we propose a new strategy for the synthesis of modified PNAs, bearing amino acid side chains. The synthesis is straightforward and is an improvement to the procedures reported so far, as it uses stable intermediates and proceeds with better yields. Copyright © Taylor & Francis Group, LLC.