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

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2004年 / 2卷 / 06期

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

页码：816 / 820

页数：5

共 49 条

[1] Structural characterization in solution of multifunctional nucleotide coordination systems [J].

Aguilar, JA ;

Celda, B ;

Fusi, V ;

García-España, E ;

Luis, SV ;

Martínez, MC ;

Ramírez, JA ;

Soriano, C ;

Tejero, R .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 2000, (07) :1323-1328

[2] MULTIFUNCTIONAL MOLECULAR RECOGNITION OF ATP, ADP AND AMP NUCLEOTIDES BY THE NOVEL RECEPTOR 2,6,10,13,17,21-HEXAAZA[22]METACYCLOPHANE [J].

AGUILAR, JA ;

GARCIAESPANA, E ;

GUERRERO, JA ;

LUIS, SV ;

LLINARES, JM ;

MIRAVET, JF ;

RAMIREZ, JA ;

SORIANO, C .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (21) :2237-2239

[3] Thermodynamics and fluorescence emission studies on potential molecular chemosensors for ATP recognition in aqueous solution [J].

Albelda, MT ;

Bernardo, MA ;

Garcia-España, E ;

Godino-Salido, ML ;

Luis, SV ;

Melo, MJ ;

Pina, F ;

Soriano, C .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1999, (11) :2545-2549

[4] New insight to the chemistry of polyaza[n]paracyclophanes.: A 15N NMR study [J].

Albelda, MT ;

Burguete, MI ;

Frías, JC ;

Garcìa-España, E ;

Luis, SV ;

Miravet, JF ;

Querol, M .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (22) :7505-7510

[5] Pertosylated polyaza[n](9,10)anthracenophanes [J].

Altava, B ;

Burguete, MI ;

Escuder, B ;

Luis, SV ;

GarciaEspana, E ;

Munoz, MC .

TETRAHEDRON, 1997, 53 (07) :2629-2640

[6] POLYAZACYCLOPHANES - 2,6,9,13-TETRAAZA[14]PARACYCLOPHANE AS A CATIONIC AND ANIONIC RECEPTOR [J].

ANDRES, A ;

BURGUETE, MI ;

GARCIAESPANA, E ;

LUIS, SV ;

MIRAVET, JF ;

SORIANO, C .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1993, (04) :749-755

[7]

ANDRES A, 1998, J ORG CHEM, V63, P1810

[8] CO2 fixation and activation by metal complexes of small polyazacyclophanes [J].

Andrés, S ;

Escuder, B ;

Doménech, A ;

García-España, E ;

Luis, SV ;

Marcelino, V ;

Llinares, JM ;

Ramírez, JA ;

Soriano, C .

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2001, 14 (07) :495-500

[9] Thermodynamics of sulfate anion binding by macrocyclic polyammonium receptors [J].

Arranz, P ;

Bencini, A ;

Bianchi, A ;

Diaz, P ;

García-España, E ;

Giorgi, C ;

Luis, SV ;

Querol, M ;

Valtancoli, B .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 2001, (09) :1765-1770

[10] Thermodynamics of phosphate and pyrophosphate anions binding by polyammonium receptors [J].

Bazzicalupi, C ;

Bencini, A ;

Bianchi, A ;

Cecchi, M ;

Escuder, B ;

Fusi, V ;

Garcia-España, E ;

Giorgi, C ;

Luis, SV ;

Maccagni, G ;

Marcelino, V ;

Paoletti, P ;

Valtancoli, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (29) :6807-6815

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