ENANTIOSELECTIVE OPTODES

被引:35
作者
HE, HR
URAY, G
WOLFBEIS, OS
机构
[1] Institute of Organic Chemistry, Karl-Franzens-University, A-8010 Graz
关键词
SPECTROPHOTOMETRY; ENANTIOSELECTIVE OPTODE; TARTRATE;
D O I
10.1016/S0003-2670(00)80958-7
中图分类号
O65 [分析化学];
学科分类号
070302 ; 081704 ;
摘要
Enantioselective optical sensors (optodes) for protonated 1-phenylethylamine, propranolol and norephedrine have been developed based on the use of four different lipophilic (R,R)-tartrates as carriers. The sensing scheme is based on the selective extraction of the organo-ammonium ions into a poly(vinylchloride) lipid membrane, and on the concomitant release of a proton from a protonated dye, contained in the PVC membrane, into the sample solution. Upon deprotonation, the dye undergoes a colour change which is optically detected. The sensor is fully reversible, with detection limits varying from 0.007 to 0.7 mM for 1-phenylethylamine, 0.006 to 0.07 mM for propranolol, and 0.7 to 7.0 mM for norephedrine at near neutral pH. Response times are about 2 min for membrane thicknesses of ca. 1-mu-m. The differences in the free energy of the two enantiomeric complexes (DELTA-DELTA-G) were calculated as well as the enantiomer selectivity coefficients (K(opt)) from the calibration curves. Although the best selectivity coefficient was found for norephedrine (0.5) using (1R,2S,5R)-dimenthyl (R,R)-tartrate as the receptor (carrier), (R,R)-di-tert.-butyl tartrate is found to be by far the most effective in all other cases. An ether of (R,R)-di-tert.-butyl tartrate, namely its O,O'-dichlorovinyl derivative, is reported for the first time as being a useful enantioselective ion carrier.
引用
收藏
页码:251 / 257
页数:7
相关论文
共 22 条
  • [1] HOST GUEST COMPLEXATION .33. SEARCH FOR NEW CHIRAL HOSTS
    ARTZ, SP
    DEGRANDPRE, MP
    CRAM, DJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (09) : 1486 - 1496
  • [2] HOST-GUEST CHEMISTRY
    CRAM, DJ
    CRAM, JM
    [J]. SCIENCE, 1974, 183 (4127) : 803 - 809
  • [3] DEROOCKER A, 1963, B SOC CHIM BELG, V72, P195
  • [4] HE H, 1990, P SPIE P SOC PHOTOIN, V1368, P172
  • [5] ENANTIOSELECTIVE OPTODE MEMBRANES WITH ENANTIOMER SELECTIVITY FOR (R)-1-PHENYLETHYLAMMONIUM AND (S)-1-PHENYLETHYLAMMONIUM IONS
    HOLY, P
    MORF, WE
    SEILER, K
    SIMON, W
    VIGNERON, JP
    [J]. HELVETICA CHIMICA ACTA, 1990, 73 (05) : 1171 - 1181
  • [6] KAYE CM, 1973, BRIT J PHARMACOL, V49, P155
  • [7] KRANTZ JC, 1930, J AM PHARM ASSOC, V19, P461
  • [8] Lehn J. M., 1988, ANGEW CHEM, V100, P91, DOI DOI 10.1002/ANGE.19881000110
  • [9] LIQUID-CHROMATOGRAPHIC SEPARATION OF ENANTIOMERIC ALKANOLAMINES VIA DIASTEREOMERIC TARTARIC ACID MONOESTERS
    LINDNER, W
    LEITNER, C
    URAY, G
    [J]. JOURNAL OF CHROMATOGRAPHY, 1984, 316 (DEC): : 605 - 616
  • [10] LINDNER W, 1987, Patent No. 4652672