Synthesis and oligodeoxynucleotide binding properties of pyrrolidinyl peptide nucleic acids bearing prolyl-2-aminocyclopentanecarboxylic acid (ACPC) backbones

被引:44
作者
Suparpprom, C
Srisuwannaket, C
Sangvanich, P
Vilaivan, T
机构
[1] Chulalongkorn Univ, Fac Sci, Dept Chem, Organ Synth Res Unit, Bangkok 10330, Thailand
[2] Chulalongkorn Univ, Fac Sci, Dept Chem, Res Ctr Bioorgan Chem, Bangkok 10330, Thailand
关键词
beta-amino acid; DNA; PNA; binding; hybridization; proline; foldamer;
D O I
10.1016/j.tetlet.2005.02.126
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of novel conformationally rigid pyrrolidinyl peptide nucleic acids (PNA) based on D-proyl-2-aminocycl opentane-carboxylic acid (ACPC) backbones has been synthesized. Investigation of the binding properties of four stereoisomeric PNAs possessing different stereochemistry at the ACPC part with DNA revealed that a precise stereochemistry of the backbone is very important in determining the binding properties. Only the PNA containing (I S,2S)-ACPC can form a very stable 1: 1 complex with the complementary DNA in a sequence-specific manner. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2833 / 2837
页数:5
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