Steroids as organising elements in anion receptors

被引:173
作者
Davis, AP [1 ]
Joos, JB [1 ]
机构
[1] Univ Bristol, Sch Chem, Bristol BS8 ITS, Avon, England
关键词
anion recognition; supramolecular chemistry; steroids; enantioselectivity; hydrogen bonding; ionophores;
D O I
10.1016/S0010-8545(03)00020-1
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The steroid nucleus has proved useful in various areas of supramolecular chemistry, acting as a building-block for extended, well-defined molecular architectures, and a scaffold for preorganised arrays of functionality. This article discusses its applications in the area of anion recognition, where cholic acid (2) has been especially valuable. The three secondary hydroxyl groups on 2 are nicely arranged for H-bond donation to a single anion, and may be converted into stronger neutral or positively-charged H-bond donors. Macrocyclic and acyclic receptors derived from 2 have been used to bind inorganic anions, carboxylates and nucleic acids. (C) 2003 Elsevier Science B.V. All rights reserved.
引用
收藏
页码:143 / 156
页数:14
相关论文
共 49 条
  • [31] Facilitated phospholipid flip-flop using synthetic steroid-derived translocases
    Lambert, TN
    Boon, JM
    Smith, BD
    Pérez-Payán, MN
    Davis, AP
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (19) : 5276 - 5277
  • [32] Steroidal guanidines as enantioselective receptors for N-acyl α-amino acids.: Part 1.: 3α-Guanylated carbamates derived from cholic acid
    Lawless, LJ
    Blackburn, AG
    Ayling, AJ
    Pérez-Payán, MN
    Davis, AP
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (11): : 1329 - 1341
  • [33] Incremental conversion of outer-membrane permeabilizers into potent antibiotics for Gram-negative bacteria
    Li, CH
    Budge, LP
    Driscoll, CD
    Willardson, BM
    Allman, GW
    Savage, PB
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (05) : 931 - 940
  • [34] Dimeric and oligomeric steroids
    Li, YX
    Dias, JR
    [J]. CHEMICAL REVIEWS, 1997, 97 (01) : 283 - 304
  • [35] On the stabilization of the syn-rotamer of amino acid carbamate derivatives by hydrogen bonding
    MarcoviciMizrahi, D
    Gottlieb, HE
    Marks, V
    Nudelman, A
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (24) : 8402 - 8406
  • [36] Sterol-polyamine conjugates as synthetic ionophores
    Merritt, M
    Lanier, M
    Deng, G
    Regen, SL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (33) : 8494 - 8501
  • [37] Miller AD, 1998, ANGEW CHEM INT EDIT, V37, P1769
  • [38] Using hydrogen bonding to control carbamate C-N rotamer equilibria
    Moraczewski, AL
    Banaszynski, LA
    From, AM
    White, CE
    Smith, BD
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (21) : 7258 - 7262
  • [39] Muller JG, 1996, J MOL RECOGNIT, V9, P143
  • [40] Oost T, 1997, LIEBIGS ANN-RECL, P1005