Synthesis of new chiral PNAs bearing a dipeptide-mimic monomer with two lysine-derived stereogenic centres

被引：54

作者：

Tedeschi, T ^{[1
]}

Sforza, S ^{[1
]}

Corradini, R ^{[1
]}

Marchelli, R ^{[1
]}

机构：

[1] Univ Parma, Dipartimento Chim Organ & Ind, I-43100 Parma, Italy

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 48期

关键词：

chiral PNA; submonomeric strategy; PNA-DNA duplexes;

D O I：

10.1016/j.tetlet.2005.09.157

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of new chiral PNA analogues based on lysine is reported. In particular, L- and/or D-lysine-based PNA submonomers bearing two lysine side chains exactly spaced as in the dipeptide Lys-Lys were synthesized and incorporated in the middle of decameric PNA strands, obtaining four diastereomeric (LD, DL, LL and DD) lysine-based chiral PNAs. The hybridization with their complementary antiparallel DNA strand was studied by melting temperature determination and compared with the analogue achiral PNA and chiral PNAs bearing one residue with either of the two lysine enantiomers. The binding abilities were shown to be strongly dependent on the configuration of the stereogenic centres. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：8395 / 8399

页数：5

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