Cyclodextrin derivatives as chiral supramolecular receptors for enantioselective sensing

被引:112
作者
Shahgaldian, Patrick [1 ]
Pieles, Uwe [1 ]
机构
[1] Univ Appl Sci NW Switzerland, Sch Life Sci, Inst Chem & Bioanalyt, CH-4132 Muttenz, Switzerland
关键词
stereoselective sensor; macrocycle; cyclodextrin; calixarene; crown-ether; supramolecular chemistry;
D O I
10.3390/s6060593
中图分类号
O65 [分析化学];
学科分类号
070302 ; 081704 ;
摘要
In view of the chiral nature of many bio-molecules ( and all bio-macromolecules), most of therapeutically active compounds which target these molecules need to be chiral and "good handed" to be effective. In addition to asymmetric synthetic and separation methodologies, enantioselective chemical sensors, able to distinguish between two enantiomers of the same molecule, are of relevance. In order to design these sensing tools, two major classes of enantioselective layers have been developed. The first is based on molecularly imprinted polymers which are produced ( polymerized) in the presence of their target, thus the polymeric material keep in "memory" the size and the shape of this molecule and the system could be used for sensing ( not reviewed here). The second approach makes use of sensitive layers containing chiral macrocyclic receptors able of stereoselective molecular recognition; these receptors are mainly based on cyclodextrins. In this contribution, are reviewed achievements in the use of native or chemically modified cyclodextrins for chiral sensing purposes ( at interfaces). Potentialities of other chiral macrocycles based on calixarenes, calix-resorcinarenes or crown-ethers as supramolecular receptors for enantioselective sensing are discussed.
引用
收藏
页码:593 / 615
页数:23
相关论文
共 95 条
[1]   Ligand orientation effects on metal-metal, ligand-ligand and metal-ligand interactions [J].
Alvarez, S ;
Palacios, AA ;
Aullón, G .
COORDINATION CHEMISTRY REVIEWS, 1999, 185-6 :431-450
[2]  
Arduini A., 1996, MACROCYCLE SYNTHESIS, P145
[3]  
Atwood J.L., 2004, Encyclopedia of Supramolecular Chemistry, DOI DOI 10.1088/0957-4484/19/26/265602
[4]   Writing patterns of molecules on molecular printboards [J].
Auletta, T ;
Dordi, B ;
Mulder, A ;
Sartori, A ;
Onclin, S ;
Bruinink, CM ;
Péter, M ;
Nijhuis, CA ;
Beijleveld, H ;
Schönherr, H ;
Vancso, GJ ;
Casnati, A ;
Ungaro, R ;
Ravoo, BJ ;
Huskens, J ;
Reinhoudt, DN .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (03) :369-373
[5]   Enantiomeric recognition of amino acids by amphiphilic crown ethers in Langmuir monolayers [J].
Badis, M ;
Tomaszkiewicz, W ;
Joly, JP ;
Rogalska, E .
LANGMUIR, 2004, 20 (15) :6259-6267
[6]   CHIRAL SENSORS BASED ON LIPOPHILIC CYCLODEXTRINS - INTERROGATION OF ENANTIOSELECTIVITY BY COMBINED NMR, STRUCTURAL CORRELATION AND ELECTRODE RESPONSE STUDIES [J].
BATES, PS ;
KATAKY, R ;
PARKER, D .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1994, (04) :669-675
[7]   A CHIRAL SENSOR BASED ON A PEROCTYLATED ALPHA-CYCLODEXTRIN [J].
BATES, PS ;
KATAKY, R ;
PARKER, D .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (02) :153-155
[8]  
Behr J. P., 1994, LOCK KEY PRINCIPLE S, V1
[9]   Diverse world of unconventional hydrogen bonds [J].
Belkova, NV ;
Shubina, ES ;
Epstein, LM .
ACCOUNTS OF CHEMICAL RESEARCH, 2005, 38 (08) :624-631
[10]  
Beulen MWJ, 2000, CHEM-EUR J, V6, P1176, DOI 10.1002/(SICI)1521-3765(20000403)6:7<1176::AID-CHEM1176>3.3.CO