Metal free, "click and click-click" conjugation of ribonucleosides and 2′-OMe oligoribonucleotides on the solid phase

被引:16
作者
Singh, Ishwar [1 ]
Heaney, Frances [1 ]
机构
[1] NUI Maynooth, Dept Chem, Maynooth, Kildare, Ireland
基金
爱尔兰科学基金会;
关键词
1,3-DIPOLAR CYCLOADDITION; TERMINAL ALKYNES; IN-VIVO; CHEMISTRY; DNA; DELIVERY; OLIGONUCLEOTIDES; NUCLEOSIDE; STRATEGIES; ANTISENSE;
D O I
10.1039/b918463e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A fast and practical metal free conjugation of ribonucleosides and 2'-OMe 4-mer oligoribonucleotides has been accomplished by a nitrile oxide alkyne click cycloaddition reaction on the solid-phase, the methodology is suited to modification at either, or both, the 3'- or the 5'-terminus of the oligoribonucleotide substrate.
引用
收藏
页码:451 / 456
页数:6
相关论文
共 29 条
[1]   Nucleoside and nucleotide analogues by catalyst free Huisgen nitrile oxide-alkyne 1,3-dipolar cycloaddition [J].
Algay, Virginie ;
Singh, Ishwar ;
Heaney, Frances .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (02) :391-397
[2]   Cu(I)-Catalyzed Huisgen Azide-Alkyne 1,3-Dipolar Cycloaddition Reaction in Nucleoside, Nucleotide, and Oligonucleotide Chemistry [J].
Amblard, Franck ;
Cho, Jong Hyun ;
Schinazi, Raymond F. .
CHEMICAL REVIEWS, 2009, 109 (09) :4207-4220
[3]   Copper-free click chemistry for dynamic in vivo imaging [J].
Baskin, Jeremy M. ;
Prescher, Jennifer A. ;
Laughlin, Scott T. ;
Agard, Nicholas J. ;
Chang, Pamela V. ;
Miller, Isaac A. ;
Lo, Anderson ;
Codelli, Julian A. ;
Bertozzi, Carolyn R. .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2007, 104 (43) :16793-16797
[4]   Comparison of a Nucleosidic vs Non-Nucleosidic Postsynthetic "Click" Modification of DNA with Base-Labile Fluorescent Probes [J].
Berndl, Sina ;
Herzig, Nadine ;
Kele, Peter ;
Lachmann, Daniel ;
Li, Xiaohua ;
Wolfbeis, Otto S. ;
Wagenknecht, Hans-Achim .
BIOCONJUGATE CHEMISTRY, 2009, 20 (03) :558-564
[5]   SYNTHESIS OF OPTICALLY-ACTIVE SILYL PROTECTED CYANOHYDRINS [J].
BRUSSEE, J ;
LOOS, WT ;
KRUSE, CG ;
VANDERGEN, A .
TETRAHEDRON, 1990, 46 (03) :979-986
[6]   Pyrene excimer signaling molecular beacons for probing nucleic acids [J].
Conlon, Patrick ;
Yang, Chaoyong James ;
Wu, Yanrong ;
Chen, Yan ;
Martinez, Karen ;
Kim, Youngmi ;
Stevens, Nathan ;
Marti, Angel A. ;
Jockusch, Steffen ;
Turro, Nicholas J. ;
Tan, Weihong .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (01) :336-342
[7]   Chemical modification: the key to clinical application of RNA interference? [J].
Corey, David R. .
JOURNAL OF CLINICAL INVESTIGATION, 2007, 117 (12) :3615-3622
[8]   Click-click-click: Single to triple modification of DNA [J].
Gramlich, Philipp M. E. ;
Warncke, Simon ;
Gierlich, Johannes ;
Carell, Thomas .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (18) :3442-3444
[9]   Synthesis of modified DNA by PCR with alkyne-bearing purines followed by a click reaction [J].
Gramlich, Philipp M. E. ;
Wirges, Christian T. ;
Gierlich, Johannes ;
Carell, Thomas .
ORGANIC LETTERS, 2008, 10 (02) :249-251
[10]   Copper-Free "Click" Modification of DNA via Nitrile Oxide-Norbornene 1,3-Dipolar Cycloaddition [J].
Gutsmiedl, Katrin ;
Wirges, Christian T. ;
Ehmke, Veronika ;
Carell, Thomas .
ORGANIC LETTERS, 2009, 11 (11) :2405-2408