Studies on the interaction of phosphate anions with N-functionalised polyaza[n] paracyclophanes:: the role of N-methylation

被引:27
作者
Albelda, MT
Frías, JC
García-España, E
Luis, SV
机构
[1] Univ Jaume 1, Dept Quim Inorgan & Organ, UA Mat Organ Avanzados, CSIC, Castellon de La Plana, Spain
[2] Univ Valencia, Dept Quim Inorgan, Valencia 46100, Spain
关键词
D O I
10.1039/b315717b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis and interaction of N, N', N", N'''-tetramethyl- 2,6,9,13-tetraaza[14] paracyclophanes (B323Me(4)) with nucleotides and inorganic phosphates is described. An easy methodology is used to de. ne thermodynamic selectivity. The interaction of B323Me4 and ATP has been monitored by H-1, P-31 NMR and by molecular mechanics, ruling out the possibility of the participation of pi-stacking interactions. Results show that N-methylation is accompanied by a strong increase in the interaction of the resulting macrocycle with ATP.
引用
收藏
页码:816 / 820
页数:5
相关论文
共 49 条
[31]   A NONCONSERVATIVE SERINE TO CYSTEINE MUTATION IN THE SULFATE-BINDING PROTEIN, A TRANSPORT RECEPTOR [J].
HE, JJ ;
QUIOCHO, FA .
SCIENCE, 1991, 251 (5000) :1479-1481
[32]  
Heuft MA, 2002, ANGEW CHEM INT EDIT, V41, P4520, DOI 10.1002/1521-3773(20021202)41:23<4520::AID-ANIE4520>3.0.CO
[33]  
2-J
[34]   High steric constraints and molecular distortion in methyl-substituted amide-based paracyclophanes and the binuclear Cu2+ complexes:: X-ray structures, NMR and absorption spectra [J].
Inoue, MB ;
Inoue, M ;
Sugich-Miranda, R ;
Machi, L ;
Velazquez, EF ;
Fernando, Q .
INORGANICA CHIMICA ACTA, 2001, 317 (1-2) :181-189
[35]   A STUDY OF NEW BIS(MACROCYCLIC POLYAMINE) LIGANDS AS INORGANIC AND ORGANIC ANION RECEPTORS [J].
KIMURA, E ;
KURAMOTO, Y ;
KOIKE, T ;
FUJIOKA, H ;
KODAMA, M .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (01) :42-46
[36]   MACROCYCLIC POLYAMINES WITH INTELLIGENT FUNCTIONS [J].
KIMURA, E .
TETRAHEDRON, 1992, 48 (30) :6175-6217
[37]   Ammonium based anion receptors [J].
Llinares, JM ;
Powell, D ;
Bowman-James, K .
COORDINATION CHEMISTRY REVIEWS, 2003, 240 (1-2) :57-75
[38]   HIGH SPECIFICITY OF A PHOSPHATE-TRANSPORT PROTEIN DETERMINED BY HYDROGEN-BONDS [J].
LUECKE, H ;
QUIOCHO, FA .
NATURE, 1990, 347 (6291) :402-406
[39]  
Metori K, 2003, HETEROCYCLES, V60, P1441
[40]   MACROMODEL - AN INTEGRATED SOFTWARE SYSTEM FOR MODELING ORGANIC AND BIOORGANIC MOLECULES USING MOLECULAR MECHANICS [J].
MOHAMADI, F ;
RICHARDS, NGJ ;
GUIDA, WC ;
LISKAMP, R ;
LIPTON, M ;
CAUFIELD, C ;
CHANG, G ;
HENDRICKSON, T ;
STILL, WC .
JOURNAL OF COMPUTATIONAL CHEMISTRY, 1990, 11 (04) :440-467