WATER-SOLUBLE RECEPTORS FOR CYCLIC-AMP AND THEIR USE FOR EVALUATING PHOSPHATE-GUANIDINIUM INTERACTIONS

被引:126
作者
KATO, Y [1 ]
CONN, MM [1 ]
REBEK, J [1 ]
机构
[1] MIT,DEPT CHEM,CAMBRIDGE,MA 02139
关键词
D O I
10.1021/ja00087a013
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A water-soluble receptor for adenosine derivatives was synthesized for the study of molecular recognition in aqueous solution. The modular receptor makes use of hydrophobic interactions, Watson-Crick and Hoogsteen hydrogen-bonding, and a phosphate-guanidinium electrostatic interaction to bind cyclic adenosine monophosphates. Measured binding affinities of 2',3/-cAMP are -3.65 and -3.26 kcal/mol at 51 and 501 mM ionic strength, respectively (H2O/D2O solution at 10 degrees C, pH 6.0). The phosphate-guanidinium interaction in this system is estimated to contribute on average 0.6 kcal/mol (51 mM ionic strength) and 0.3 kcal/mol (501 mM ionic strength) to binding. The maximum value of a phosphate-guanidinium electrostatic interaction is estimated to be 2.4 kcal/mol in water.
引用
收藏
页码:3279 / 3284
页数:6
相关论文
共 33 条
  • [1] CHEMISTRY OF SYNTHETIC RECEPTORS AND FUNCTIONAL-GROUP ARRAYS .10. ORDERLY FUNCTIONAL-GROUP DYADS - RECOGNITION OF BIOTIN AND ADENINE-DERIVATIVES BY A NEW SYNTHETIC HOST
    ADRIAN, JC
    WILCOX, CS
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (20) : 8055 - 8057
  • [2] MOLECULAR RECOGNITION WITH CONVERGENT FUNCTIONAL-GROUPS .6. SYNTHETIC AND STRUCTURAL STUDIES WITH A MODEL RECEPTOR FOR NUCLEIC-ACID COMPONENTS
    ASKEW, B
    BALLESTER, P
    BUHR, C
    JEONG, KS
    JONES, S
    PARRIS, K
    WILLIAMS, K
    REBEK, J
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (03) : 1082 - 1090
  • [3] CONVERGENT FUNCTIONAL-GROUPS .13. HIGH-AFFINITY COMPLEXATION OF ADENOSINE DERIVATIVES WITHIN INDUCED BINDING POCKETS
    CONN, MM
    DESLONGCHAMPS, G
    DEMENDOZA, J
    REBEK, J
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (09) : 3548 - 3557
  • [4] Connors K.A., 1987, BINDING CONSTANTS ME, P411
  • [5] A SYNTHETIC RECEPTOR FOR CYCLIC ADENOSINE-MONOPHOSPHATE
    DESLONGCHAMPS, G
    GALAN, A
    DEMENDOZA, J
    REBEK, J
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1992, 31 (01): : 61 - 63
  • [6] DOIG AJ, 1992, J AM CHEM SOC, V114, P338, DOI 10.1021/ja00027a044
  • [7] HYDROGEN-BONDING AND BIOLOGICAL SPECIFICITY ANALYZED BY PROTEIN ENGINEERING
    FERSHT, AR
    SHI, JP
    KNILLJONES, J
    LOWE, DM
    WILKINSON, AJ
    BLOW, DM
    BRICK, P
    CARTER, P
    WAYE, MMY
    WINTER, G
    [J]. NATURE, 1985, 314 (6008) : 235 - 238
  • [8] A SYNTHETIC RECEPTOR FOR DINUCLEOTIDES
    GALAN, A
    DEMENDOZA, J
    TOIRON, C
    BRUIX, M
    DESLONGCHAMPS, G
    REBEK, J
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (24) : 9424 - 9425
  • [9] SELECTIVE COMPLEXATION OF ADENOSINE-MONOPHOSPHATE NUCLEOTIDES BY RIGID BICYCLIC GUANIDINIUM ABIOTIC RECEPTORS
    GALAN, A
    PUEYO, E
    SALMERON, A
    DEMENDOZA, J
    [J]. TETRAHEDRON LETTERS, 1991, 32 (15) : 1827 - 1830
  • [10] THE FREE-ENERGY CHANGE OF RESTRICTING A BOND ROTATION IN THE BINDING OF PEPTIDE ANALOGS TO VANCOMYCIN GROUP ANTIBIOTICS
    GERHARD, U
    SEARLE, MS
    WILLIAMS, DH
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1993, 3 (05) : 803 - 808