Polymer supported calixarene derivative useful for solid-phase synthesis application

被引:6
作者
Granata, Giuseppe [1 ,2 ]
Consoli, Grazia M. L. [1 ]
Sciuto, Sebastiano [3 ]
Geraci, Corrada [1 ]
机构
[1] CNR, Ist Chim Biomol, I-95126 Catania, Italy
[2] Univ Catania, Dipartimento Sci Farmaceut, I-95125 Catania, Italy
[3] Univ Catania, Dipartimento Sci Chim, I-95125 Catania, Italy
关键词
Anchored-calixarene; Polymeric resin; Solid-phase synthesis; Phosphoramidite chemistry; Nucleotide-calixarene; STATIONARY PHASES; LIBRARY; PRECONCENTRATION; FIBER; AMIDE;
D O I
10.1016/j.tetlet.2010.09.082
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A calix[4]arene derivative has been anchored to carboxyl CPG and TentaGel supports by an easily cleavable ester bond and DMT groups allow a simple loading evaluation via UV-vis spectroscopy. The loading of the calixarene on TentaGel resin has also been estimated by HR-MAS NMR experiments. The potential of the polymer supported calixarenes (9 and 10) in solid phase synthesis has been tested by condensation of four thymine nucleotide units onto the upper rim of the calix[4]arene skeleton. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6139 / 6142
页数:4
相关论文
共 44 条
[1]   Use of controlled pore glass in solid phase oligosaccharide synthesis. Application to the semiautomated synthesis of a glyconucleotide conjugate [J].
Adinolfi, M ;
Barone, G ;
De Napoli, L ;
Iadonisi, A ;
Piccialli, G .
TETRAHEDRON LETTERS, 1998, 39 (14) :1953-1956
[2]   Synthesis and ion-binding affinities of calix[4]arenes immobilized on cross-linked polystyrene [J].
Alexandratos, SD ;
Natesan, S .
MACROMOLECULES, 2001, 34 (02) :206-210
[3]  
Asfari Z., 2001, Calixarene (2001), Ed
[4]   The synthesis of novel polymer-bound calix[4]arenes [J].
Barata, PD ;
Costa, AI ;
Granja, P ;
Prata, JV .
REACTIVE & FUNCTIONAL POLYMERS, 2004, 61 (01) :147-151
[5]   A neutral uranyl dimeric complex and remarkable extraction properties of a 1-acid 3-diethyl amide substituted calix[4]arene ligand [J].
Beer, PD ;
Drew, MGB ;
Hesek, D ;
Kan, M ;
Nicholson, G ;
Schmitt, P ;
Sheen, PD ;
Williams, G .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1998, (17) :2783-2785
[6]  
Bohme V., 2003, CHEM PHENOLS
[7]   Synthesis of a peptidocalix[4]arene library and identification of compounds with hydrolytic activity [J].
Brewster, RE ;
Dalton, BGA ;
Shuker, SB .
BIOORGANIC CHEMISTRY, 2005, 33 (01) :16-21
[8]   Novel nucleotide-calixarene conjugates via phosphoester linkage [J].
Consoli, GML ;
Granata, G ;
Galante, E ;
Cunsolo, F ;
Geraci, C .
TETRAHEDRON LETTERS, 2006, 47 (19) :3245-3249
[9]   Spontaneous self-assembly of water-soluble nucleotide-calixarene conjugates in small micelles coalescing to microspheres [J].
Consoli, Grazia M. L. ;
Granata, Giuseppe ;
Lo Nigro, Raffaella ;
Malandrino, Graziella ;
Geraci, Corrada .
LANGMUIR, 2008, 24 (12) :6194-6200
[10]   Self-assembly of a nucleotide-calixarene hybrid in a triangular supramolecule [J].
Consoli, Grazia M. L. ;
Granata, Giuseppe ;
Garozzo, Domenico ;
Mecca, Tommaso ;
Geraci, Corrada .
TETRAHEDRON LETTERS, 2007, 48 (45) :7974-7977