Chiral calix[4]arenes bearing amino alcohol functionality as membrane carriers for transport of chiral amino acid methylesters and mandelic acid

被引:24
作者
Bozkurt, Selahattin [1 ]
Yilmaz, Mustafa [1 ]
Sirit, Abdulkadir [1 ]
机构
[1] Selcuk Univ, Dept Chem, TR-42099 Konya, Turkey
关键词
chiral calix[4]arene; bulk liquid membrane; amino acid methyl esters; mandelic acid; transport rate; BULK LIQUID-MEMBRANE; ENANTIOSELECTIVE TRANSPORT; ENANTIOMERIC RECOGNITION; SEPARATION; EXTRACTION; DERIVATIVES; RESOLUTION; PROPRANOLOL; CALIXARENES; POTASSIUM;
D O I
10.1002/chir.21034
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Novel chiral calix[4]arene derivatives bearing amino alcohol moieties at the lower rim have been synthesized from the reaction of p-tert-butylcalix[4]arene diester with various amino alcohols. The transport of amino acid esters (phenylglycine, phenylalanine, and tryptophan methyl esters hydrochloride) and mandelic acid were studied through chloroform bulk liquid membrane system using chiral calix[4]arenes 15-20. All these receptors have been found to act as carriers for transport of aromatic amino acid methylesters and mandelic acid from the aqueous source phase to the aqueous receiving phase. The influence of calixarene and guest structures upon transport through liquid membrane is discussed. Chirality 24: 129-136, 2012. (c) 2011 Wiley Periodicals, Inc.
引用
收藏
页码:129 / 136
页数:8
相关论文
共 55 条
  • [1] ABE Y, 1995, CHEM PHARM BULL, V43, P262
  • [2] Recent advances in chiral resolution through membrane-based approaches
    Afonso, CAM
    Crespo, JG
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (40) : 5293 - 5295
  • [3] OPTICAL ISOMER SEPARATION BY LIQUID-CHROMATOGRAPHY
    ARMSTRONG, DW
    [J]. ANALYTICAL CHEMISTRY, 1987, 59 (02) : A84 - &
  • [4] SEPARATION OF DRUG STEREOISOMERS BY THE FORMATION OF BETA-CYCLODEXTRIN INCLUSION COMPLEXES
    ARMSTRONG, DW
    WARD, TJ
    ARMSTRONG, RD
    BEESLEY, TE
    [J]. SCIENCE, 1986, 232 (4754) : 1132 - 1135
  • [5] ARMSTRONG DW, 1988, CRIT REV ANAL CHEM, V19, P175
  • [6] Chiral lariat ethers as membrane carriers for chiral amino acids and their sodium and potassium salts
    Aydin, Isil
    Aral, Tarik
    Karakaplan, Mehmet
    Hosgoren, Halil
    [J]. TETRAHEDRON-ASYMMETRY, 2009, 20 (02) : 179 - 183
  • [7] Baragaña B, 2002, CHEM-EUR J, V8, P2931, DOI 10.1002/1521-3765(20020703)8:13<2931::AID-CHEM2931>3.0.CO
  • [8] 2-H
  • [9] Beer PD, 2001, ANGEW CHEM INT EDIT, V40, P486, DOI 10.1002/1521-3773(20010202)40:3<486::AID-ANIE486>3.0.CO
  • [10] 2-P