Novel nucleic acid architectures involving locked nucleic acid (LNA) and pyrene residues: Results from an Indo-Danish collaboration

被引：4

作者：

Babu, BR

Raunak

Sorensen, MD

Hrdlicka, PJ

Trikha, S

Prasad, AK

Parmar, VS

Wengel, J

机构：

[1] Univ So Denmark, Dept Chem, Nucl Acid Ctr, DK-5230 Odense M, Denmark

[2] Univ Delhi, Dept Chem, Bioorgan Lab, Delhi 110007, India

[3] Univ Copenhagen, Dept Chem, DK-2100 Copenhagen, Denmark

来源：

PURE AND APPLIED CHEMISTRY | 2005年 / 77卷 / 01期

关键词：

D O I：

10.1351/pac200577010319

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We report herein our results for locked nucleic acid (LNA)-type oligonucleotides containing pyrene residues. Pyrene has a large hydrophobic and planar surface area and is therefore a potential intercalating unit; furthermore, it is interesting as a fluorescent tag when covalently bound to DNA. Synthesis and hybridization of conformationally locked universal base surrogates are described together with efficient interstrand communication as shown by the formation of pyrene excimer bands for duplexes containing 2'-N-(pyren- I -yl)methyl-2'amino-LNA monomers positioned in a zipper-like manner within a DNA duplex.

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页码：319 / 326

页数：8

相关论文

共 35 条

[1] Conformationally locked aryl C-nucleosides:: synthesis of phosphoramidite monomers and incorporation into single-stranded DNA and LNA (locked nucleic acid) [J].

Babu, BR ;

Prasad, AK ;

Trikha, S ;

Thorup, N ;

Parmar, VS ;

Wengel, J .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (22) :2509-2519

[2] Universal hybridization using LNA (locked nucleic acid) containing a novel pyrene LNA nucleotide monomer [J].

Babu, BR ;

Wengel, J .

CHEMICAL COMMUNICATIONS, 2001, (20) :2114-2115

[3] Universal bases for hybridization, replication and chain termination [J].

Berger, M ;

Wu, YQ ;

Ogawa, AK ;

McMinn, DL ;

Schultz, PG ;

Romesberg, FE .

NUCLEIC ACIDS RESEARCH, 2000, 28 (15) :2911-2914

[4] Pyrenemethyl ara-uridine-2′-carbamate:: A strong interstrand excimer in the major groove of a DNA duplex [J].

Dioubankova, NN ;

Malakhov, AD ;

Stetsenko, DA ;

Gait, MJ ;

Volynsky, PE ;

Efremov, RG ;

Korshun, VA .

CHEMBIOCHEM, 2003, 4 (09) :841-847

[5] Effective synthesis of C-nucleosides with 2′,4′-BNA modification [J].

Hari, Y ;

Obika, S ;

Sakaki, M ;

Morio, KI ;

Yamagata, Y ;

Imanishia, T .

TETRAHEDRON, 2002, 58 (15) :3051-3063

[6] Interstrand communication between 2′-N-(pyren-1-yl)methyl-2′-amino-LNA monomers in nucleic acid duplexes:: directional control and signalling of full complementarity [J].

Hrdlicka, PJ ;

Babu, BR ;

Sorensen, MD ;

Wengel, J .

CHEMICAL COMMUNICATIONS, 2004, (13) :1478-1479

[7]

Kool ET, 2000, ANGEW CHEM INT EDIT, V39, P990, DOI 10.1002/(SICI)1521-3773(20000317)39:6<990::AID-ANIE990>3.0.CO

[8]

2-0

[9] LNA (Locked Nucleic Acids): Synthesis of the adenine, cytosine, guanine, 5-methylcytosine, thymine and uracil bicyclonucleoside monomers, oligomerisation, and unprecedented nucleic acid recognition [J].

Koshkin, AA ;

Singh, SK ;

Nielsen, P ;

Rajwanshi, VK ;

Kumar, R ;

Meldgaard, M ;

Olsen, CE ;

Wengel, J .

TETRAHEDRON, 1998, 54 (14) :3607-3630

[10] A simplified and efficient route to 2′-O, 4′-C-methylene-linked bicyclic ribonucleosides (locked nucleic acid) [J].

Koshkin, AA ;

Fensholdt, J ;

Pfundheller, HM ;

Lomholt, C .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (25) :8504-8512

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