Backbone extended pyrrolidine PNA (bepPNA):: a chiral PNA for selective RNA recognition

被引：17

作者：

Govindaraju, T ^{[1
]}

Kumar, VA ^{[1
]}

机构：

[1] Natl Chem Lab, Div Organ Chem Synth, Pune 411008, Maharashtra, India

来源：

TETRAHEDRON | 2006年 / 62卷 / 10期

关键词：

peptide nucleic acids; bepPNA; RNA recognition;

D O I：

10.1016/j.tet.2005.12.002

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthesis of cationic, chiral PNA analogues with an extra atom in the backbone (bepPNA) is reported. The (2S,4S) geometry of the pyrrolidine ring, and an additional carbon atom in the backbone of homopyrimidine-bepPNAs resulted in the optimization of the inter-nucleobase distance, such that selective binding to complementary RNA over DNA was observed in the triplex mode. It was evident from circular dichroism studies that oligomers with mixed aminoethylglycyl-bep (aeg-bep) repeating units, and also bepPNA with homogeneous backbone attained structures quite different from those of aegPNA(2):RNA/DNA complexes. The bepPNA. when incorporated in a duplex forming mixed purine-pyrimidine sequence, also showed a preference for binding complementary RNA over DNA. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：2321 / 2330

页数：10

共 58 条

[1]

Agrawal S., 1993, PROTOCOLS OLIGONUCLE, V20

[2] ALKYL PHOSPHOTRIESTERS OF DINUCLEOTIDES AND OLIGONUCLEOTIDES .5. INHIBITORY EFFECT OF COMPLEX-FORMATION WITH OLIGODEOXYRIBONUCLEOTIDE ETHYL PHOSPHOTRIESTERS ON TRANSFER RIBONUCLEIC-ACID AMINOACYLATION [J].

BARRETT, JC ;

MILLER, PS ;

TSO, POP .

BIOCHEMISTRY, 1974, 13 (24) :4897-4906

[3]

BENNETT CF, 1998, APPL ANTISENSE OLIGO

[4] Novel antisense and peptide nucleic acid strategies for controlling gene expression [J].

Braasch, DA ;

Corey, DR .

BIOCHEMISTRY, 2002, 41 (14) :4503-4510

[5] Locked nucleic acid (LNA): fine-tuning the recognition of DNA and RNA [J].

Braasch, DA ;

Corey, DR .

CHEMISTRY & BIOLOGY, 2001, 8 (01) :1-7

[6]

CANTOR CR, 1980, BIOPHYS CHEM 3, P624

[7]

Christensen L, 1995, J Pept Sci, V1, P175

[8] SYNTHESIS OF A CARBOXAMIDE LINKED T-ASTERISK-T DIMER AND ITS INCORPORATION IN OLIGONUCLEOTIDES [J].

CHUR, A ;

HOLST, B ;

DAHL, O ;

VALENTINHANSEN, P ;

PEDERSEN, EB .

NUCLEIC ACIDS RESEARCH, 1993, 21 (22) :5179-5183

[9] THE BENZOYLATION OF URACIL AND THYMINE [J].

CRUICKSHANK, KA ;

JIRICNY, J ;

REESE, CB .

TETRAHEDRON LETTERS, 1984, 25 (06) :681-684

[10] Functional genomics and target validation approaches using antisense oligonucleotide technology [J].

Dean, NM .

CURRENT OPINION IN BIOTECHNOLOGY, 2001, 12 (06) :622-625

← 1 2 3 4 5 6 →