Conformational behavior and magnetic properties of a nitroxide amino acid derivative in vacuo and in aqueous solution(238 views) D'Amore M, Improta R, Barone V
J Phys Chem A (ISSN: 1089-5639, 1520-5215electronic), 2003; 107(32): 6264-6269.
Dipartimento di Chimica, Universita Federico II, Complesso Univ. Monte S.Angelo, via Cintia, I-80126 Napoli, Italy
Ist. di Biostrutture e Bioimmagini, CNR, via Mezzocannone 6, I-80134 Naples, Italy
References: Rassat, A., Key, P., (1967) Bull. Soc. Chim. Fr., p. 81
Nakaie, C.L., Goissis, G., Schreirer, S., Paiva, A.C.M., (1981) Braz. J. Med. Biol. Res., 14, p. 173
Marchetto, R., Shreier, S., Nakaie, C.R., (1993) J. Am. Chem. Soc., 115, p. 11042
Smythe, M.L., Nakaie, C.R., Marshall, G.R., (1995) J. Am. Chem. Soc., 117, p. 10555
Toniolo, C., Crisma, M., Formaggio, F., (1998) Biopolymers, 47, p. 153
Pispisa, B., Mazza, C., Palleschi, A., Stella, L., Venanzi, M., Formaggio, F., Toniolo, C., Broxterman, Q.B., (2002) Biopolymers, 67, p. 247
Crisma, M., Bianco, A., Formaggio, F., Toniolo, C., Kamphuis, J., (1995) Lett. Pept. Sci., 2, p. 187
Bui, T.T.T., Formaggio, F., Crisma, M., Torraca, V., Toniolo, C., Hussein, R., Siligardi, G., (2000) J. Chem. Soc., Perkin Trans., 2, p. 1043
Toniolo, C., Valente, E., Formaggio, F., Crisma, M., Pilloni, G., Corvaja, C., Toffoletti, A., Flippen-Anderson, J.L., (1995) J. Pept. Sci., 1, p. 45
Marshall, G.R., (1971) Infra-science Chemical Reports, pp. 305-316. , Kharash, N., Ed.
Gordon and Breach: New York
Karle, I.L., Balaram, P., (1990) Biochemistry, 29, p. 6747
Toniolo, C., Benedetti, E., (1991) Macromolecules, 24, p. 4004
Improta, R., Barone, V., Kudin, K.N., Scuseria, G.E., (2001) J. Am. Chem. Soc., 123, p. 3311
Improta, R., Rega, N., Aleman, C., Barone, V., (2001) Macromolecules, 34, p. 7550
Cornish, V.W., Benson, D.R., Altenbach, C.A., Hideg, K., Hubbel, W.L., Scultz, P.G., (1994) Proc. Natl. Acad. Sci. U.S.A., 91, pp. 2910-2914
Hanson, P., Millhauser, G., Formaggio, F., Crisma, M., Toniolo, C., (1996) J. Am. Chem. Soc., 118, p. 7618
Barone, V., (1995) Recent Advances in Density Functional Methods, p. 287. , Chong, D. P., Ed.
World Scientific: Singapore
Barone, V., Bencini, A., Di Matteo, A., (1997) J. Am. Chem. Soc., 119, p. 10831
Adamo, C., Subra, R., Di Matteo, A., Barone, V., (1998) J. Chem. Phys., 109, p. 10244
Adamo, C., Di Matteo, A., Rey, P., Barone, V., (1999) J. Phys. Chem. A, 103, p. 348
Di Matteo, A., Adamo, C., Cossi, M., Barone, V., Rey, P., (1999) Chem. Phys. Lett., 310, p. 159
Improta, R., Di Matteo, A., Barone, V., (2000) Theor. Chem. Acc., 104, p. 273
Improta, R., Scalmani, G., Barone, V., (2001) Chem. Phys. Lett., 336, p. 349
Improta, R., Kudin, K.N., Scuseria, G.E., Barone, V., (2002) J. Am. Chem. Soc., 124, p. 113
Tedeschi, A.M., D'Errico, G., Busi, E., Basosi, R., Barone, V., (2002) Phys. Chem. Chem. Phys., 4, p. 2180
Saracino, G.A.A., Tedeschi, A., D'Errico, G., Improta, R., Franco, L., Ruzzi, M., Corvaia, C., Barone, V., (2002) J. Phys. Chem. A, 106, p. 10700
Improta, R., Benzi, C., Barone, V., (2001) J. Am. Chem. Soc., 123, p. 12568
Langella, E., Improta, R., Barone, V., (2002) J. Am. Chem. Soc., 124, p. 11531
Perdew, J.P., Burke, K., Ernzerhof, M., (1996) Phys. Rev. Lett., 77, p. 3685
Adamo, C., Barone, V., (1999) J. Chem. Phys., 110, p. 6158
Weltener, W., (1989) Magnetic Atoms and Molecules, , Dover: New York
Barone, V., Lelj, F., Russo, N., Ellinger, Y., Subra, R., (1985) Chem. Phys., 76, p. 385
Sekino, H., Bartlett, R.J., (1985) J. Chem. Phys., 82, p. 4225
Barone, V., Grand, A., Minichino, C., Subra, R., (1993) J. Phys. Chem., 97, p. 6355
Perera, S.A., Salemi, L.N., Bartlett, R.J., (1997) J. Chem. Phys., 706, p. 4061
Dapprich, S., Komaroni, I., Byun, K.S., Morokuna, K., Frisch, M.J., (1999) J. Mol. Struct.: THEOCHEM, 461, p. 1
Cossi, M., Scalmani, G., Rega, N., Barone, V., (2002) J. Chem. Phys., 117, p. 43
Barone, V., Cossi, M., Tomasi, J., (1997) J. Chem. Phys., 707, p. 3210
Floris, F.M., Tomasi, J., (1986) J. Comput. Chem., 70, p. 616
Pierotti, R.A., (1976) Chem. Rev., 76, p. 717
Cremer, D., Pople, J.A., (1975) J. Am. Chem. Soc., 97, p. 1354
Monaco, V., Formaggio, F., Crisma, M., Toniolo, C., Hanson, P., Milhauser, G.L., (1999) Biopolymers, 50, p. 239
Nakaie, C. L., Goissis, G., Schreirer, S., Paiva, A. C. M., (1981) Braz. J. Med. Biol. Res., 14, p. 173
Smythe, M. L., Nakaie, C. R., Marshall, G. R., (1995) J. Am. Chem. Soc., 117, p. 10555
Bui, T. T. T., Formaggio, F., Crisma, M., Torraca, V., Toniolo, C., Hussein, R., Siligardi, G., (2000) J. Chem. Soc., Perkin Trans., 2, p. 1043
Karle, I. L., Balaram, P., (1990) Biochemistry, 29, p. 6747
Cornish, V. W., Benson, D. R., Altenbach, C. A., Hideg, K., Hubbel, W. L., Scultz, P. G., (1994) Proc. Natl. Acad. Sci. U. S. A., 91, pp. 2910-2914
Tedeschi, A. M., D'Errico, G., Busi, E., Basosi, R., Barone, V., (2002) Phys. Chem. Chem. Phys., 4, p. 2180
Saracino, G. A. A., Tedeschi, A., D'Errico, G., Improta, R., Franco, L., Ruzzi, M., Corvaia, C., Barone, V., (2002) J. Phys. Chem. A, 106, p. 10700
Perdew, J. P., Burke, K., Ernzerhof, M., (1996) Phys. Rev. Lett., 77, p. 3685
Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Zakrzewski, V. G., Pople, J. A., (2000) Gaussian 99, Development Version, Revision A. 03, , Gaussian, Inc.: Pittsburgh, PA
Foresman, J. B., Frisch, A. E., (1996) Exploring Chemistry with Electronic Structure Methods, 2nd Ed., , Gaussian Inc.: Pittsburgh PA
Chipman, D. M., (1989) Theor. Chim. Acta, 76, p. 73
Hariraran, P. C., Pople, J. A., (1973) Theor. Chim. Acta, 23, p. 213
Perera, S. A., Salemi, L. N., Bartlett, R. J., (1997) J. Chem. Phys., 706, p. 4061
Floris, F. M., Tomasi, J., (1986) J. Comput. Chem., 70, p. 616
Pierotti, R. A., (1976) Chem. Rev., 76, p. 717
Conformational behavior and magnetic properties of a nitroxide amino acid derivative in vacuo and in aqueous solution
The conformational behavior and magnetic properties of the α-acetylamino, N′-methylamide derivative of TOAC (4-amino-2, 2, 6.6-tetramethylpiperidine-l-oxyl-4-carboxylic acid) have been investigated in vacuo and in aqueous solution by an integrated computational approach including density functional, post-Hartree Fock, and continuum solvent models. According to our computations, piperidine rings with an equatorial placement of the nitroxide moiety are more stable by about 1 kcal/mol than their axial counterparts both in vacuo and in aqueous solution. With respect to natural residues, TOAC shows a marked preference for helical conformers, which is further enhanced by polar solvents. A comparison with other C α-tetrasubstituted residues points out the difference between cyclic and open-chain substituents. The nitrogen isotropic hyperfine coupling constants (AN) of folded TOAC conformers are similar to those of other nitroxides involving six-membered rings and are well reproduced by a composite QM/QM/PCM model. The AN values of extended TOAC conformers are significantly lower because of the constrained nearly planar structure of the piperidine ring.
Conformational behavior and magnetic properties of a nitroxide amino acid derivative in vacuo and in aqueous solution
Kállay C, Dávid A, Timári S, Nagy EM, Sanna D, Garribba E, Micera G, De Bona P, Pappalardo G, Rizzarelli E, Sóvágó I * Copper(II) complexes of rat amylin fragments(360 views) Dalton T (ISSN: 1477-9234, 1477-9226, 1477-9234electronic), 2011 Oct 14; 40(38): 9711-9721. Impact Factor:3.838 ViewExport to BibTeXExport to EndNote
Testino G, Leone S, Fagoonee S, Del Bas JM, Rodriguez B, Puiggros F, Marine S, Rodriguez MA, Morina D, Armengol L, Caimari A, Arola L, Cimini FA, Barchetta I, Carotti S, Bertoccini L, Baroni MG, Vespasiani-gentilucci U, Cavallo MG, Morini S, Nelson JE, Roth CL, Wilson LA, Yates KP, Aouizerat B, Morgan-stevenson V, Whalen E, Hoofnagle A, Mason M, Gersuk V, Yeh MM, Kowdley KV, Lee SM, Jun DW, Cho YK, Jang KS, Kucukazman M, Ata N, Dal K, Yeniova AO, Kefeli A, Basyigit S, Aktas B, Akin KO, Agladioglu K, Ure OS, Topal F, Nazligul Y, Beyan E, Ertugrul DT, Catena C, Cosma C, Camozzi V, Plebani M, Ermani M, Sechi LA, Fallo F, Goto Y, Ray MB, Mendenhall CL, French SW, Gartside PS Serum vitamin A deficiency and increased intrahepatic expression of cytokeratin antigen in alcoholic liver disease(615 views) Hepatology (ISSN: 1827-1669electronic, 0026-4806linking), 1988 Sep; 83120693611123109(5): 1019-1026. Impact Factor:0.913 ViewExport to BibTeXExport to EndNote