Enantioselective recognition of carbamate-type molecular tweezers derived from deoxycholic acid for amino acid methyl esters

被引:0
|
作者
Xue, CH [1 ]
Mu, QM [1 ]
Chen, SH [1 ]
机构
[1] Sichuan Univ, Fac Chem, Chengdu 610064, Peoples R China
关键词
molecular tweezers; deoxycholic acid; amino acid methyl ester; enantioselective recognition;
D O I
暂无
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
New chiral molecular tweezers 1 similar to 4 have been synthesized by using deoxycholic acid as a spacer to bridge the different aromatic amines. Their structures were confirmed by IR, H-1 NMR and elemental analysis. Enantioselective recognition properties of these molecular tweezers for amino acid methyl esters have been investigated by UV-vis spectra titration in CHCl3 at 25 degreesC. The results indicate that molecular tweezers 1 - 4 not only recognize all amino acid methyl esters examined but also possess higher selectivity for D-amino acid methyl esters. The recognition ability and selectivity axe discussed from the viewpoint of the size/shape-fit and geometrical complementary relationship between the molecular tweezers and amino acid methyl esters.
引用
收藏
页码:355 / 359
页数:5
相关论文
共 9 条
  • [1] Steroidal guanidinium receptors for the enantioselective recognition of N-acyl α-amino acids
    Davis, AP
    Lawless, LJ
    [J]. CHEMICAL COMMUNICATIONS, 1999, (01) : 9 - 10
  • [2] HU R, 1999, J SICHUAN U, V4, P800
  • [3] LI DH, 1997, THESIS SICHUAN U CHE
  • [4] Enantioselective recognition of amino acids by beta-cyclodextrin 6-O-monophosphates
    Liu, Y
    Bin, L
    Han, BH
    Li, YM
    Chen, RT
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1997, (07): : 1275 - 1278
  • [5] Lu GY, 2000, ACTA CHIM SINICA, V58, P890
  • [6] MAXWELL JC, 1995, J CHEM SOC CHEM COMM, P1925
  • [7] Molecular recognition and phase transfer of underivatized amino acids by a foldable artificial host
    Metzger, A
    Gloe, K
    Stephan, H
    Schmidtchen, FP
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (06): : 2051 - 2055
  • [8] Xue CH, 2000, ACTA CHIM SINICA, V58, P717
  • [9] Enantiomeric recognition of amine compounds by chiral macrocyclic receptors
    Zhang, XX
    Bradshaw, JS
    Izatt, RM
    [J]. CHEMICAL REVIEWS, 1997, 97 (08) : 3313 - 3361