Design of a new oligotriazole peptide nucleic acid analogue (oT-PNA)

被引:8
作者
Vergnaud, Julien [1 ]
Faugeras, Pierre-Antoine [1 ]
Chaleix, Vincent [1 ]
Champavier, Yves [2 ]
Zerrouki, Rachida [1 ]
机构
[1] Fac Sci & Tech, Lab Chim Subst Nat EA1069, F-87060 Limoges, France
[2] Univ Limoges, Serv Commun RMN, Fac Pharm, F-87025 Limoges, France
关键词
Peptide nucleic acid; Click chemistry; Microwave chemistry; Synthesis design; MICROWAVE-ASSISTED SYNTHESIS; CLICK CHEMISTRY; TERMINAL ALKYNES; DNA; OLIGONUCLEOTIDES; CYCLOADDITION; INHIBITORS; LIGATION; THYMINE; AZIDES;
D O I
10.1016/j.tetlet.2011.09.050
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We describe in this Letter the synthesis of an original thymine azido-heterotrimer generated by Click Chemistry. This trimer has been obtained from an azido-thymidine and a new chloroethyl-propargylated PNA monomer analogue, after two azidation/click-reaction cycles. Conformational preferences of a rotameric intermediate have also been studied (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6185 / 6189
页数:5
相关论文
共 33 条
[1]   Precise Synthesis of Molecularly Defined Oligomers and Polymers by Orthogonal Iterative Divergent/Convergent Approaches [J].
Binauld, Sandra ;
Damiron, Denis ;
Connal, Luke A. ;
Hawker, Craig J. ;
Drockenmuller, Eric .
MACROMOLECULAR RAPID COMMUNICATIONS, 2011, 32 (02) :147-168
[2]   A Modular Approach to Functionalized and Expanded Crown Ether Based Macrocycles Using Click Chemistry [J].
Binauld, Sandra ;
Hawker, Craig J. ;
Fleury, Etienne ;
Drockenmuller, Eric .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (36) :6654-6658
[3]   1,2,3-triazole as a peptide surrogate in the rapid synthesis of HIV-1 protease inhibitors [J].
Brik, A ;
Alexandratos, J ;
Lin, YC ;
Elder, JH ;
Olson, AJ ;
Wlodawer, A ;
Goodsell, DS ;
Wong, CH .
CHEMBIOCHEM, 2005, 6 (07) :1167-+
[4]  
CHEN SM, 1994, TETRAHEDRON LETT, V35, P5091
[5]   Clickable peptide nucleic acids (cPNA) with tunable affinity [J].
Chouikhi, Dalila ;
Barluenga, Sofia ;
Winssinger, Nicolas .
CHEMICAL COMMUNICATIONS, 2010, 46 (30) :5476-5478
[6]   Conformational and supramolecular properties of main chain and cyclic click oligotriazoles and polytriazoles [J].
Chow, Hak-Fun ;
Lau, Kwun-Ngai ;
Ke, Zhihai ;
Liang, Yuting ;
Lo, Chui-Man .
CHEMICAL COMMUNICATIONS, 2010, 46 (20) :3437-3453
[7]  
Drew M. G. B., 2001, Angew. Chem., V113, P2373
[8]   PNA HYBRIDIZES TO COMPLEMENTARY OLIGONUCLEOTIDES OBEYING THE WATSON-CRICK HYDROGEN-BONDING RULES [J].
EGHOLM, M ;
BUCHARDT, O ;
CHRISTENSEN, L ;
BEHRENS, C ;
FREIER, SM ;
DRIVER, DA ;
BERG, RH ;
KIM, SK ;
NORDEN, B ;
NIELSEN, PE .
NATURE, 1993, 365 (6446) :566-568
[9]  
ELIEL EL, 1994, STEREOCHEMISTRY ORGA, P511
[10]   Synthesis and biological activity of mustard derivatives of thymine [J].
Hadj-Bouazza, Amel ;
Teste, Karine ;
Colombeau, Ludovic ;
Chaleix, Vincent ;
Zerrouki, Rachida ;
Kraemer, Michel ;
Sainte Catherine, Odile .
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2008, 27 (05) :439-448