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 (122 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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Pietropaolo A, Raiola L, Muccioli L, Tiberio G, Zannoni C, Fattorusso R, Isernia C, La Mendola D, Pappalardo G, Rizzarelli E
* An NMR and molecular dynamics investigation of the avian prion hexarepeat conformational features in solution (136 visite)
Chemical Physics Letters (ISSN: 0009-2614), 2007 Jul 6; 442(1-3): 110-118.
Impact Factor: 2.207
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Bonomo RP, Cucinotta V, Giuffrida A, Impellizzeri G, Magrì A, Pappalardo G, Rizzarelli E, Santoro AM, Tabbì G, Vagliasindi LI
* A re-investigation of copper coordination in the octa-repeats region of the prion protein (120 visite)
Dalton Trans (ISSN: 1477-9226, 1477-9234, 1477-9234electronic), 2005 Jan 7; (1): 150-158.
Impact Factor: 3.003
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Impellizzeri G, D'Alessandro F, Pappalardo G, Tringali C
* Synthesis And Structural Characterisation Of Two Novel Diastereoisomeric Naproxen-Appended Beta-Cyclodextrin Derivatives (102 visite)
J Incl Phenom (ISSN: 0923-0750), 2005; 51(3-4): 173-180.
Impact Factor: 1.02
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Falcigno L, Oliva R, D'Auria G, Maletta M, Dettin M, Pasquato A, Di Bello C, Paolillo L
* Structural investigation of the HIV-1 envelope glycoprotein gp160 cleavage site 3: Role of site-specific mutations (111 visite)
Chembiochem (ISSN: 1439-4227, 1439-7633, 1439-7633electronic), 2004 Dec 3; 5(12): 1653-1661.
Impact Factor: 3.474
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Mineo P, Vitalini D, La Mendola D, Rizzarelli E, Scamporrino E, Vecchio G
* Coordination Features Of Difunctionalized Beta-Cyclodextrins With Carnosine: Esi-Ms And Spectroscopic Investigations On 6a, 6d-Di-(beta-Alanyl-L-Histidine)-6a, 6d-Dideoxy-Beta-Cyclodextrin And 6a, 6c-Di-(beta-Alanyl-L-Histidine)-6a, 6c-Dideoxy-Beta-Cyclodextrin And Their Copper (ii) Complexes (135 visite)
J Chem Res (ISSN: 1873-3344, 0162-0134, 0162-0134print), 2004 Feb; 98(2): 254-265.
Impact Factor: 2.225
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Bonomo RP, Castronovo BM, Santoro AM
* A Spectroscopic Investigation Of The Interaction Between Nitrogen Monoxide And Copper Sites Of The Fungal Laccase From Rigidoporus Lignosus (75 visite)
Dalton Trans, 2004 Jan 7; N/D: 104-112.
Impact Factor: 4.097
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Oliva R, Falcigno L, D'Auria G, Gargiulo D, Dettin M, Pasquato A, Di Bello C, Paolillo L
* Structural investigation of the HIV-1 envelope glycoprotein gp160 cleavage site: Solution conformation of a 41-mer peptide (88 visite)
Peptide Revolution, 2004; N/D: N/D-N/D.
Impact Factor: 4.659
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Improta R, Santoro F, Dietl C, Papastathopoulos E, Gerber G
* Time dependent DFT investigation on the two lowest 1B u states of the trans isomer of stilbene and stiff-stilbenes (118 visite)
Chemical Physics Letters (ISSN: 0009-2614), 2004; 387(4-6): 509-516.
Impact Factor: 2.438
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Oliva R, Falcigno L, D'Auria G, Dettin M, Scarinci C, Pasquato A, Di Bello C, Paolillo L
* Structural investigation of the HIV-1 envelope glycoprotein gp160 cleavage site (110 visite)
Chembiochem (ISSN: 1439-4227, 1439-7633, 1439-7633electronic), 2003 Sep 4; 4(8): 727-733.
Impact Factor: 3.992
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Oliva R, Falcigno L, D'Auria G, Dettin M, Scarinci C, Pasquato A, Di Bello C, Paolillo L
* Structural investigation of the HIV-1 envelope glycoprotein gp160 cleavage site, 2: relevance of an N-terminal helix (81 visite)
Chembiochem (ISSN: 1439-4227, 1439-7633, 1439-7633electronic), 2003 Aug 4; 4(8): 727-733.
Impact Factor: 2.92
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Oliva R, Leone M, Falcigno L, D'Auria G, Dettin M, Scarinci C, Di Bello C, Paolillo L
* Structural investigation of the HIV-1 envelope glycoprotein gp160 cleavage site (114 visite)
Chemistry (ISSN: 0947-6539, 1521-3765, 1521-3765electronic), 2002 Mar 15; 8(6): 1467-1473.
Impact Factor: 4.238
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Impellizzeri G, Pappalardo G, D'Alessandro F, Rizzarelli E, Saviano M, Iacovino R, Benedetti E, Pedone C
Erratum: Solid state and solution conformation of 6-{4-[N-tert- butoxycarbonyl-N-(N'-ethyl)propanamide]imidazolyl}-6- deoxycyclomaltoheptaose: Evidence of self-inclusion of the boc group within the β-cyclodextrin cavity (European Journal of Organic Chemistry (2000) (1065-1076)) (118 visite)
Eur J Org Chem (ISSN: 1434-193x), 2000; (12): 2345-2345.
Impact Factor: 2.15
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Impellizzeri G, Pappalardo G, D'Alessandro F, Rizzarelli E, Saviano M, Iacovino R, Benedetti E, Pedone C
Solid state and solution conformation of 6-{4-[N-tert-butoxycarbonyl-N- (N'-ethyl)propanamide]imidazolyl}-6-deoxycyclomaltoheptaose: Evidence of self-inclusion of the Boc group within the β-cyclodextrin cavity (106 visite)
European J Org Chem (ISSN: 1434-193x), 2000; (6): 1065-1076.
Impact Factor: 2.15
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48 Records (42 escludendo Abstract e Conferenze).
Impact factor totale: 147.654 (133.075 escludendo Abstract e Conferenze).
Impact factor a 5 anni totale: 168.407 (152.887 escludendo Abstract e Conferenze).







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