Enantioselective recognition of amino acids by chiral peptido-calix[4]arenes and thiacalix[4]arenes

被引:18
作者
Bois, Joackim [1 ,2 ]
Bonnamour, Isabelle [1 ,2 ]
Duchamp, Christian [1 ,2 ]
Parrot-Lopez, Helene [1 ,2 ]
Darbost, Ulrich [1 ,2 ]
Felix, Caroline [1 ,2 ]
机构
[1] Univ Lyon 1, CNRS, UMR 5246, Inst Chim & Biochim Mol & Supramol,CSAp, F-69622 Villeurbanne, France
[2] Univ Lyon, Lyon, France
关键词
ELECTROSPRAY MASS-SPECTROMETRY; ENANTIOMERIC RECOGNITION; OPTICALLY PURE; DERIVATIVES; BEARING; RECEPTORS; PHENYLALANINE; COMPLEXATION; TRYPTOPHAN; PHASE;
D O I
10.1039/b907190c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In order to prepare new molecular hosts able to discriminate enantiomers of amino-acid derivatives, we have synthesized chiral thiacalix[4]arenes. Extensive studies using NMR and mass spectrometry techniques allow us to determine the major supramolecular interactions involved in the recognition process. Moreover, a titration study enables us to determine the binding constant between these new hosts and a series of amino-acid derivatives. Finally, we have also demonstrated that these calixarenes are able to discriminate enantiomers of amino-acid guests.
引用
收藏
页码:2128 / 2135
页数:8
相关论文
共 45 条
  • [1] Chiral recognition in gas-phase cyclodextrin: Amino acid complexes - Is the three point interaction still valid in the gas phase?
    Ahn, S
    Ramirez, J
    Grigorean, G
    Lebrilla, CB
    [J]. JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY, 2001, 12 (03) : 278 - 287
  • [2] Synthesis and structure of lower rim C-linked tetra-N-tosyl peptidocalix[4]arenes
    Ben Sdira, S
    Baudry, R
    Felix, CP
    Giudicelli, MBA
    Lamartine, RJ
    [J]. TETRAHEDRON LETTERS, 2004, 45 (41) : 7801 - 7804
  • [3] Synthesis and structure of lower rim C-linked N-tosyl peptidocalix[4]arenes
    Ben Sdira, S
    Felix, CP
    Giudicelli, MBA
    Seigle-Ferrand, PF
    Perrin, M
    Lamartine, RJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (17) : 6632 - 6638
  • [4] A SPECTROPHOTOMETRIC INVESTIGATION OF THE INTERACTION OF IODINE WITH AROMATIC HYDROCARBONS
    BENESI, HA
    HILDEBRAND, JH
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1949, 71 (08) : 2703 - 2707
  • [5] Upper rim appended hybrid calixarenes via click chemistry
    Bew, Sean P.
    Brimage, Rebecca A.
    L'Hermite, Nathalie
    Sharma, Sunil V.
    [J]. ORGANIC LETTERS, 2007, 9 (19) : 3713 - 3716
  • [6] Bis(diamido)-bridged basket resorcin[4]arenes as enantioselective receptors for amino acids and amines
    Botta, Bruno
    D'Acquarica, Ilaria
    Nevola, Laura
    Sacco, Fabiola
    Lopez, Zara Valbuena
    Zappia, Giovanni
    Fraschetti, Caterina
    Speranza, Maurizio
    Tafi, Andrea
    Caporuscio, Fabiana
    Letzel, Matthias C.
    Mattay, Jochen
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (36) : 5995 - 6002
  • [7] Calixarene-based chiral phase-transfer catalysts derived from cinchona alkaloids for enantioselective synthesis of α-amino acids
    Bozkurt, Selahattin
    Durmaz, Mustafa
    Yilmaz, Mustafa
    Sirit, Abdulkadir
    [J]. TETRAHEDRON-ASYMMETRY, 2008, 19 (05) : 618 - 623
  • [8] The use of electrospray mass spectrometry (ES/MS) for the differential detection of some steroids as calix-[n]-arene sulphonate complexes
    Da Silva, E
    Valmalle, C
    Becchi, M
    Cuilleron, CY
    Coleman, AW
    [J]. JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY, 2003, 46 (1-2) : 65 - 69
  • [9] Optically pure calix[6]tris-ammoniums: Syntheses and host-guest properties toward neutral guests
    Darbost, U
    Zeng, XS
    Giorgi, M
    Jabin, I
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (25) : 10552 - 10560
  • [10] Enantiomeric recognition of amino acid derivatives by chiral Schiff bases of calix[4]arene
    Durmaz, Mustafa
    Alpaydin, Sabri
    Sirit, Abdulkadir
    Yilmaz, Mustafa
    [J]. TETRAHEDRON-ASYMMETRY, 2007, 18 (07) : 900 - 905