Affinity and Selectivity of C2-and C5-Substituted "Chiral-Box" PNA in Solution and on Microarrays

作者：Manicardi Alex; Calabretta Alessandro; Bencivenni Mariangela; Tedeschi Tullia; Sforza Stefano; Corradini Roberto^*; Marchelli Rosangela

来源：Chirality, 2010, 22(1E): E161-E172.

DOI：10.1002/chir.20865

• PNA
• DNA recognition
• chiral monomers
• single nucleotide polymorphisms
• microarrays

Two peptide nucleic acids (PNAs) containing three adjacent modified chiral monomers (chiral box) were synthesized. The chiral monomers contained either a C2- or a C5-modified backbone, synthesized starting from D-and L-arginine, respectively (2D- and 5L-PNA). The C2-modified chiral PNA was synthesized using a submonomeric strategy to avoid epimerization during solid-phase synthesis, whereas for the C5-derivative, the monomers were first obtained and then used in solid-phase synthesis. The melting temperature of these PNA duplexes formed with the full-match or with single-mismatch DNA were measured both by UV and by CD spectroscopy and compared with the unmodified PNA. The 5L-chiral-box-PNA showed the highest T(m) with full-match DNA, whereas the 2D-chiral-box-PNA showed the highest sequence selectivity. The PNA were spotted on microarray slides and then hybridized with Cy5-labeled full match and mismatched oligonucleotides. The results obtained showed a signal intensity in the order achiral > 2D-chiral box > 5L-chiral box, whereas the full-match/mismatch selectivity was higher for the 2D chiral box PNA. Chirality 22:E161-E172, 2010.

• 出版日期2010