Solution structure of R2Sn(iv)-β-N-acetyl-neuraminate (R = Me, Bu) complexes in D2O and DMSO-d6: Experimental NMR and DFT computational study

Dalton Transactions

Volumn , Issue 14, 2007, Pages 1440-1446

  Bertazzi, Nuccio ^a   Casella, Girolamo ^a   Ferrante, Francesco ^a   Pellerito, Lorenzo ^a   Rotondo, Archimede ^b   Rotondo, Enrico ^b  

^a UNIVERSITY OF PALERMO   (Italy)

^b UNIVERSITY OF MESSINA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALKOXIDE ATOMS; GALACTONONULOSIC ACID; MONOSACCHARIDE BIDENTATE;

BINDING SITES; CHELATION; COORDINATION REACTIONS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROBABILITY DENSITY FUNCTION;

AROMATIC COMPOUNDS;

DEUTERIUM OXIDE; DIBUTYL(N ACETYLNEURAMINIC ACID)TIN(IV); DIBUTYL(N-ACETYLNEURAMINIC ACID)TIN(IV); DIMETHYL SULFOXIDE; DIMETHYL(N ACETYLNEURAMINIC ACID)TIN(IV); DIMETHYL(N-ACETYLNEURAMINIC ACID)TIN(IV); NEURAMINIC ACID DERIVATIVE; ORGANOTIN COMPOUND; SIALIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; MATHEMATICAL COMPUTING; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SOLUTION AND SOLUBILITY;

DEUTERIUM OXIDE; DIMETHYL SULFOXIDE; MAGNETIC RESONANCE SPECTROSCOPY; MATHEMATICAL COMPUTING; MOLECULAR STRUCTURE; NEURAMINIC ACIDS; ORGANOTIN COMPOUNDS; SIALIC ACIDS; SOLUTIONS;

EID: 33947697964     PISSN: 14779226     EISSN: 14779234     Source Type: Journal    
DOI: 10.1039/b616330k     Document Type: Article

References (38)

1. F. G. Blix A. Gottschalk E. Klenk Nature 1957 179 1088
2. G. M. W. Cook and R. W. Stoddart, in Surface Carbohydrates of the Eukaryotic Cell, Academic Press, New York, 1973, pp. 56-97
3. H. Wiegandt, in New Comprehensive Biochemistry: Glycolipids, ed., A. Neuberger, and, L. L. M. van Deenen, Elsevier, New York, 1985, vol. 10, pp. 28-36
4. D. A. Cheresh M. D. Pierschbacker M. A. Herzig K. J. Mujoo J. Cell Biol. 1986 102 688 696
5. G. R. Moe S. Tan D. M. Granoff FEMS Immunol. Med. Microbiol. 1999 26 209 226
6. M. J. Kiefel M. von Itzstein Chem. Rev. 2002 102 471 490
7. E. H. Eylar M. A. Mandof O. V. Brody J. L. Oncley J. Biol. Chem. 1962 237 1992 2000
8. R. Schauer A. K. Shukla C. Schröeder E. Muller Pure Appl. Chem. 1984 56 907
9. T. Angata A. Varki Chem. Rev. 2002 102 439 469
10. J. P. Behr J. M. Lehn FEBS Lett. 1972 22 178 180
11. L. W. Jaques E. L. Brown J. M. Barrett W. S. Brey, Jr. W. Weltner, Jr. J. Biol. Chem. 1977 252 4533 4538
12. M. Saladini L. Menabue E. Ferrari J. Inorg. Biochem. 2002 88 61 68
13. R. Barbieri L. Pellerito G. Ruisi M. T. Lo Giudice Inorg. Chim. Acta 1982 6 39 40
14. N. Bertazzi, G. Casella, P. D'Agati, T. Fiore, C. Mansueto, V. Mansueto, L. Nagy, C. Pellerito, L. Pellerito, I. D. Sciacca and M. Scopelliti, presented in part at the 4th Symposium on Pharmaco-Bio-Metallics, Lecce (IT), October, 2004
15. B. Gyurcsik L. Nagy Coord. Chem. Rev. 2000 203 81 149
16. N. Bertazzi G. Bruschetta G. Casella L. Pellerito E. Rotondo M. Scopelliti Appl. Organomet. Chem. 2003 17 932 939
17. N. Buzás L. Nagy E. Kuzmann A. Vértes K. Burger Inorg. Chim. Acta 1998 274 167 176
18. T. B. Grindley Adv. Carbohydr. Chem. Biochem. 1998 53 17 142
19. P. J. Smith A. P. Tupiauskas Annu. Rep. NMR Spectrosc. 1978 8 291 370
20. R. Hani R. A. Geanagel Coord. Chem. Rev. 1982 44 229 246
21. B. Wrackmeyer Annu. Rep. NMR Spectrosc. 1985 16 73 186
22. B. Wrackmeyer Annu. Rep. NMR Spectrosc. 1999 38 203 264
23. R. Vivas-Reyes F. De Proft M. Biesemans R. Willem P. Geerlings J. Phys. Chem. A 2002 106 2753 2759
24. P. Avalle R. K. Harris R. D. Fischer Phys. Chem. Chem. Phys. 2002 4 3558 3561
25. P. Avalle R. K. Harris P. B. Kardakov P. J. Wilson Phys. Chem. Chem. Phys. 2002 4 5925 5932
26. A. Bagno G. Casella G. Saielli J. Chem. Theor. Comput. 2006 2 37 46
27. A. Bagno N. Bertazzi G. Casella L. Pellerito G. Saielli I. D. Sciacca J. Phys. Org. Chem. 2006 19 874 883
28. C. A. G. Haasnoot F. A. A. M. dew Leeuw C. Altona Tetrahedron 1980 36 2783 2792
29. T. P. Lockhart W. F. Manders Inorg. Chem. 1986 25 892 895
30. T. P. Lockhart W. F. Manders J. J. Zuckerman J. Am. Chem. Soc. 1985 107 4547 4548
31. J. A. Zubieta J. J. Zuckerman Prog. Inorg. Chem. 1978 24 251 475
32. W. P. Neumann, in The Organic Chemistry of Tin, ed., D. Seyferth, Interscience Publishers, London, 1970, pp. 211-212
33. J. D. Donaldson S. G. Grimes L. Pellerito M. A. Girasolo P. J. Smith A. Cambria M. Famà Polyhedron 1987 6 383 386
34. A. D. Becke J. Chem. Phys. 1993 98 5648 5652
35. C. Lee W. Yang R. G. Parr Phys. Rev. B 1988 37 785 789
36. N. Godbout D. R. Salahub J. Andzelm E. Wimmer Can. J. Chem. 1992 70 560 571
37. W. Kutzelnigg, U. Fleischer and M. Schindler, in NMR Basic Principles and Progress, Springer, Heidelberg, 1990, pp. 165-262
38. Gaussian 03, Revision C.01, Gaussian, Inc., Wallingford CT, 2004, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez and J. A. Pople