Inclusion of naturally occurring amino acids in water soluble calix[4]arenes: A microcalorimetric and 1H NMR investigation supported by molecular modeling
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Inclusion of naturally occurring amino acids in water soluble calix[4]arenes: A microcalorimetric and 1H NMR investigation supported by molecular modeling (170 visite)

Arena G, Casnati A, Contino A, Magrì A, Sansone F, Sciotto D, Ungaro R

Org Biomol Chem (ISSN: 1477-0520, 1477-0539, 1477-0539electronic), 2006 Jan 21; 4(2): 243-249.



Tipo di articolo: Journal Article,

Impact factor: 2.874, Impact factor a 5 anni: 3.389

Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-33645684785&partnerID=40&md5=2f378ff346b8e80ce1de386055170691

Parole chiave: Buffer-Dependent Changes, Calorimetric Titrations, Cone Conformation, Sulfonated Calix[4]arenes, Binding Energy, Enthalpy, Hydrogen Bonds, Nuclear Magnetic Resonance, Olefins, Amino Acids, Calix(4)arene, Calixarene, Phenol Derivative, Sulfonic Acid Derivative, Article, Chemical Structure, Chemistry, Metabolism, Nuclear Magnetic Resonance Spectroscopy, Solubility, Structure Activity Relation, Thermodynamics, Models, Molecular, Molecular Conformation, Structure-Activity Relationship, Sulfonated Calix [4] Arenes, Calix (4) Arene,

Affiliazioni:

*** IBB - CNR ***
Dipartimento di Scienze Chimiche, Università di Catania, Viale A. Doria 6, 95125, Catania, Italy
C.I.R.C.M.S.B., Piazza Umberto I, 1, 70121, Bari, Italy
Dipartimento di Chimica Organica e Industriale, Università di Parma, Parco Area delle Scienze 17/A, I-43100, Parma, Italy
Istituto di Biostrutture e Bioimmagini, CNR, Catania, Viale A. Doria 6, 95125, Catania, Italy
C. I. R. C. M. S. B., Piazza Umberto I, 1, 70121, Bari, Italy


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The thermodynamic parameters for the inclusion of some naturally occurring amino acids into a series of p-sulfonated calix[4]arenes, were determined via both 1H NMR and calorimetric titrations in buffered aqueous solution at 25 °C. The calorimetric data show that inclusion is enthalpically driven in all cases, regardless of flexibility of the host and the nature of the guest. The most efficient receptor is the calix[4]arene tetrasulfonate 1, which exists in solution at pH 7 in a cone conformation, stiffened by H-bonding at the lower rim. Molecular mechanics data help in the understanding of why some hosts do not form inclusion complexes at all. The comparison of our data with literature reports shows that there are dramatic buffer-dependent changes in the binding affinities. © The Royal Society of Chemistry 2006.
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Mercier Y, Santoro F, Reguero M, Improta R
* The decay from the dark nπ* excited state in uracil: An integrated CASPT2/CASSCF and PCM/TD-DFT study in the gas phase and in water (148 visite)
J Phys Chem B (ISSN: 1520-6106, 1520-5207, 1520-5207electronic), 2008 Sep 4; 112(35): 10769-10772.
Impact Factor: 4.189
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Rotondo A, Rotondo E, Casella GA, Grasso G
* Tin(IV) catalyzed D-galacturonic acid anomerization (156 visite)
Dalton T (ISSN: 1477-9226, 1477-9234, 1477-9234electronic), 2008 Feb 7; (5): 596-601.
Impact Factor: 3.58
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D'Andrea LD, Testa I, Panico M, Di Stasi R, Carac C, Tarallo L, Arra C, Barbieri A, Romanelli A, Aloj L
* In vivo and in vitro characterization of CCK8 bearing a histidine-based chelator labeled with Tc-99m-tricarbonyl (224 visite)
Biopolymers (ISSN: 0006-3525, 0006-6352, 0006-3525print), 2008; 90(5): 707-712.
Impact Factor: 2.823
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Osz K, Nagy Z, Pappalardo G, Di Natale G, Sanna D, Micera G, Rizzarelli E, Sóvágó I
* Copper(II) interaction with prion peptide fragments encompassing histidine residues within and outside the octarepeat domain: speciation, stability constants and binding details (215 visite)
Chemistry (ISSN: 0947-6539, 1521-3765, 1521-3765electronic), 2007; 13(25): 7129-7143.
Impact Factor: 5.33
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Pailot A, D'Ambrosio K, Corbier C, Talfournier F, Branlant G
* Invariant Thr(244) is essential for the efficient acylation step of the non-phosphorylating glyceraldehyde-3-phosphate dehydrogenase from Streptococcus mutans (148 visite)
Biochem J (ISSN: 0264-6021, 1470-8728electronic, 0264-6021linking), 2006 Dec 15; 400: 521-530.
Impact Factor: 4.1
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Alterio V, Vitale RM, Monti SM, Pedone C, Scozzafava A, Cecchi A, De Simone G, Supuran CT
* Carbonic anhydrase inhibitors: X-ray and molecular modeling study for the interaction of a fluorescent antitumor sulfonamide with isozyme II and IX (171 visite)
J Am Chem Soc (ISSN: 0002-7863, 0002-2786, 1520-5126), 2006 Jun 28; 128(25): 8329-8335.
Impact Factor: 7.696
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Zielenkiewicz W, Swierzewski R, Attanasio F, Rialdi G
* Thermochemical, volumetric and spectroscopic properties of lysozyme-poly(ethylene) glycol system (129 visite)
Journal Of Thermal Analysis And Calorimetry (ISSN: 1388-6150), 2006; 83(3): 587-595.
Impact Factor: 1.438
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Santelli E, Leone M, Li C, Fukushima T, Preece NE, Olson AJ, Ely KR, Reed JC, Pellecchia M, Liddington RC, Matsuzawa S-I
* Structural analysis of Siah1-Siah-interacting protein interactions and insights into the assembly of an E3 ligase multiprotein complex (184 visite)
Jbc Papers (ISSN: 0021-9258, 1083-351x, 0021-9258linking), 2005 Oct 7; 280(40): 34278-34287.
Impact Factor: 5.854
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De Luca S, Sanseverino M, Zocchi I, Pedone C, Morelli G, Ragone R
* Receptor fragment approach to the binding between CCK8 peptide and cholecystokinin receptors: A fluorescence study on type B receptor fragment CCKB-R (352-379) (175 visite)
Biopolymers (ISSN: 0006-3525, 0006-6352, 0006-3525print), 2005 Mar; 77(4): 205-211.
Impact Factor: 2.545
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Farrera-Sinfreu J, Zaccaro L, Vidal D, Salvatella X, Giralt E, Pons M, Albericio F, Royo M
* A New Class of Foldamers Based on cis-γ-Amino-L-proline (219 visite)
J Am Chem Soc (ISSN: 0002-7863, 0002-2786, 1520-5126), 2004 May 19; 126(19): 6048-6057.
Impact Factor: 6.903
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Improta R, Barone V
* Assesing the reliability of density functional methods in the conformational study of polypeptides: The treatment of intraresidue nonbonding interactions (211 visite)
J Comput Chem (ISSN: 0192-8651, 1096-987xelectronic), 2004; 25(11): 1333-1341.
Impact Factor: 3.168
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Barone V, Formaggio F, Improta R, Polo F, Maran F
* Electron transfer to and conformational preferences of Aib oligo-peptides (212 visite)
Proc Electrochem Soc, 2004; 10: 29-32.
Impact Factor: 0
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Mansi R, Tesauro D, De Capua A, Fattorusso R, Carac C, Aloj L, Benedetti E, Morelli G
* Peptide-chelating agent conjugate for selective targeting of somatostatin receptor type 1: Synthesis and characterization (241 visite)
Biopolymers (ISSN: 0006-3525, 0006-6352, 0006-3525print), 2004; 76(6): 527-534.
Impact Factor: 2.863
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Guzzi R, Milardi D, La Rosa C, Grasso D, Verbeet MP, Canters GW, Sportelli L
* The effect of copper/zinc replacement on the folding free energy of wild type and Cys3Ala/Cys26Ala azurin (144 visite)
Int J Biol Macromol (ISSN: 0141-8130, 0141-8130linking, 1879-0003electronic), 2003 Jan 15; 31(4-5): 163-170.
Impact Factor: 1.427
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Formaggio F, Bonchio M, Crisma M, Peggion C, Mezzato S, Polese A, Barazza A, Antonello S, Maran F, Broxterman QB, Kaptein B, Kamphuis J, Vitale RM, Saviano M, Benedetti E, Toniolo C
* Nitroxyl peptides as catalysts of enantioselective oxidations (217 visite)
Chemistry (ISSN: 0947-6539, 1521-3765, 1521-3765electronic), 2002; 8(1): [d]84-93.
Impact Factor: 4.238
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Saviano G, Rossi F, Benedetti E, Pedone C, Mierke DF, Maione A, Zanotti G, Tancredi T, Saviano M
* Structural consequences of metal complexation of cyclo[Pro-Phe-Phe-Ala-Xaa]2 decapeptides (211 visite)
Chemistry (ISSN: 0947-6539, 1521-3765, 1521-3765electronic), 2001 Mar 16; 7(6): 1176-1183.
Impact Factor: 4.614
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Grasso D, Milardi D, La Rosa C, Rizzarelli E
* DSC study of the interaction of the prion peptide PrP106-126 with artificial membranes (169 visite)
New J Chem (ISSN: 1144-0546), 2001; 25(12): 1543-1548.
Impact Factor: 2.44
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Martínez JC, Viguera AR, Berisio R, Wilmanns M, Mateo PL, Filimonov VV, Serrano L
Thermodynamic analysis of α-spectrin SH3 and two of its circular permutants with different loop lengths: Discerning the reasons for rapid folding in proteins (166 visite)
Biochemistry (ISSN: 0006-2960, 1520-4995, 1520-4995electronic), 1999 Jan 12; 38(2): 549-559.
Impact Factor: 4.493
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Crisma M, Formaggio F, Valle G, Toniolo C, Saviano M, Iacovino R, Zaccaro L, Benedetti E
Experimental evidence at atomic resolution for intramolecular N- H···π (phenyl) interactions in a family of amino acid derivatives (202 visite)
Biopolymers (ISSN: 0006-3525, 0006-6352, 0006-3525print), 1997; 42(1): 1-6.
Impact Factor: 2.425
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Lombardi A, Saviano M, Nastri F, Maglio O, Mazzeo M, Pedone C, Isernia C, Pavone V
Unusual conformational preferences of β-alanine containing cyclic peptides. VII (223 visite)
Biopolymers (ISSN: 0006-3525, 0006-6352, 0006-3525print), 1996 Jun; 38(6): 683-691.
Impact Factor: 2.425
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Veldman N, Spek AL, Tabbì G, Driessen WL, Reedijk J
A dinuclear nickel(II) compound: μ-{N, N, N′, N′-tetrakis[2-(3, 5-dimethyl-1-pyrazolyl)ethyl]-1, 2- ethylenediamine}-bis[aqua(nitrato-Ο, Ο + ′)nickel(II)] dinitrate dimethanol solvate (102 visite)
Acta Crystallogr Sect C Cryst Struct Commun (ISSN: 0108-2701), 1996; 52(11): 2698-2701.
Impact Factor: 0.459
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Rossi F, Saviano M, Di Talia P, Di Blasio B, Pedone C, Zanotti G, Mosca M, Saviano G, Tancredi T, Ziegler K, Benedetti E
Solution and solid state structure of an aib-containing cyclodecapeptide inhibiting the cholate uptake in hepatocytes (195 visite)
Biopolymers (ISSN: 0006-3525, 0006-6352, 0006-3525print), 1996; 40(5): 465-478.
Impact Factor: 2.425
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54 Records (54 escludendo Abstract e Conferenze).
Impact factor totale: 242.199 (242.199 escludendo Abstract e Conferenze).
Impact factor a 5 anni totale: 263.493 (263.493 escludendo Abstract e Conferenze).







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Ultima modifica di Marco Comerci in data Thursday 19 March 2015, 14:43:36
170 visite. Ultima visita in data Monday 20 January 2020, 19:45:13