Conformational study of the natural iron chelator myo-inositol 1,2,3-trisphosphate using restrained/flexible analogues and computational analysis

Tetrahedron

Volumn 66, Issue 46, 2010, Pages 8949-8957

  Mansell, David ^a   Veiga, Nicolás ^b   Torres, Julia ^b   Etchells, Laura L ^a   Bryce, Richard A ^a   Kremer, Carlos ^b   Freeman, Sally ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

^b UNIVERSIDAD DE LA REPÚBLICA   (Uruguay)

Author keywords

Chair conformation; Computational analysis; Inositol phosphates; Iron chelation; Myo Inositol 1,2,3 trisphosphate

Indexed keywords

1 (DIBENZYL PHOSPHO) 2,3 ISOPROPYLIDENE GLYCEROL; 1 (DIBENZYL PHOSPHO) GLYCEROL; 1,2,3 TRIS (DIBENZYL PHOSPHO) GLYCEROL; 1,2,3 TRISPHOSPHOGLYCEROL; 4,6 CARBONATE MYO INOSITOL; 4,6 CARBONATE MYO INOSITOL 1,2,3,5 TETRAKIS (DIBENZYL PHOSPHATE); 4,6 CARBONATE MYO INOSITOL 1,2,3,5 TETRAKISPHOSPHATE; 4,6 DIBENZYL MYO INOSITOL 1,2,3,5 TETRAKIS (DIBENZYL PHOSPHATE); 4,6 METHYLENE MYO INOSITOL; 4,6 METHYLENE MYO INOSITOL 1,2,3,5 TETRAKIS (DIBENZYL PHOSPHATE); CHELATING AGENT; GLYCEROL; HYDROXYL RADICAL; INOSITOL TRISPHOSPHATE; MYO INOSITOL 1,2,3,5 TETRAKISPHOSPHATE; MYOINOSITOL 1,2,3 TRISPHOSPHATE; PENTASODIUM 4,6 CARBONATE MYO INOSITOL 1,2,3,5 TETRAKISPHOSPHATE; TETRASODIUM 1,2,3 TRISPHOSPHOGLYCEROL; UNCLASSIFIED DRUG;

ANTIOXIDANT ACTIVITY; ARTICLE; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; IRON CHELATION; MATHEMATICAL ANALYSIS; PRIORITY JOURNAL; SYNTHESIS;

MAMMALIA;

EID: 77958177391     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.09.033     Document Type: Article

References (28)

1. I.D. Spiers, C.J. Barker, S.-K. Chung, Y.-T. Chang, S. Freeman, J.M. Gardiner, P.H. Hirst, P.A. Lambert, R.H. Michell, D.R. Poyner, C.H. Schwalbe, A.W. Smith, and K.R.H. Solomons Carbohydr. Res. 282 1996 81 99
2. I.D. Spiers, S. Freeman, D.R. Poyner, and C.H. Schwalbe Tetrahedron Lett. 36 1995 2125 2128
3. E. Graf, K.L. Empson, and J.W. Eaton J. Biol. Chem. 262 1987 11647 11650
4. P.T. Hawkins, D.R. Poyner, T.R. Jackson, A.J. Letcher, D.A. Lander, and R.F. Irvine Biochem. J. 294 1993 929 934
5. N. Veiga, J. Torres, D. Mansell, S. Freeman, S. Dominguez, C.J. Barker, A. Diaz, and C. Kremer J. Biol. Inorg. Chem. 14 2009 51 59
6. I.D. Spiers, S. Freeman, and C.H. Schwalbe J. Chem. Soc., Chem. Commun. 1995 2219 2220
7. D. Mansell, N. Rattray, L.L. Etchells, C.H. Schwalbe, A.J. Blake, E.V. Bichenkova, R.A. Bryce, C.J. Barker, A. Diaz, C. Kremer, and S. Freeman Chem. Commun. 2008 5161 5163
8. Mansell, D.; Rattray, N.; Etchells, L.L.; Schwalbe, C.H.; Blake, A.J.; Torres, J.; Kremer, C.; Bichenkova, E.V.; Barker, C.J.; Freeman, S. Org. Biomol. Chem. 2010, 8, 2850-2858.
9. B.Q. Phillippy, and E. Graf Free Radic. Biol. Med. 22 1997 939 946
10. E. Graf, J.R. Mahoney, R.G. Bryant, and J.W. Eaton J. Biol. Chem. 259 1984 3620 3624
11. S.J. Angyal Carbohydr. Res. 325 2000 313 320
12. T. Praveen, and M.S. Shashidhar Carbohydr. Res. 330 2001 409 411
13. D.G. Norman, C.B. Reese, and H.T. Serafinowska Synthesis 1985 751 754
14. K.S. Kim, and W.A. Szarek Synthesis 1978 48 50
15. K.C. Nicolaou, H.J. Mitchell, K.C. Fylaktakidou, R.M. Rodriguez, and H. Suzuki Chem. - Eur. J. 6 2000 3116 3148
16. T.-H. Kim, and A.B. Holmes J. Korean Chem. Soc. 50 2006 129 136
17. M. Ryan, M.P. Smith, T.K. Vinod, W.L. Lau, J.F.W. Keana, and O.H. Griffith J. Med. Chem. 39 1996 4366 4376
18. M. Šala, J. Kolar, M. Strlič, and M. Kočevar Carbohydr. Res. 341 2006 897 902
19. S.-K. Chung, and Y.-T. Chang J. Chem. Soc., Chem. Commun. 1995 11 12
20. S.M. Klein, G. Cohen, and A.I. Cederbaum Biochemistry 20 1981 6006 6012
21. T. Nash Biochem. J. 55 1953 416 421
22. C.J. Volkmann, G.M. Chateauneuf, J. Pradhan, A.T. Bauman, R.E. Brown, and P.P.N. Murthy Tetrahedron Lett. 43 2002 4853 4856
23. H.W. Lee, and Y. Kishi J. Org. Chem. 50 1985 4402 4404
24. K. Laumen, and O. Ghisalba Biosci. Biotechnol. Biochem. 58 1994 2046 2049
25. A.D. Becke J. Chem. Phys. 98 1993 5648 5652
26. C. Lee, W. Yang, and R.G. Parr Phys. Rev. B: Condens. Matter 37 1988 785 789
27. P.J. Hay, and W.R. Wadt J. Chem. Phys. 82 1985 270 283
28. Frisch, M.J.; Trucks, G.W.; Schlegel, H.B.; Scuseria, G.E.; Robb, M.A.; Cheeseman, J.R.; Montgomery, J.A.; Vreven, T.; Kudin, K.N.; Burant, J.C.; Millam, J.M.; Iyengar, S.S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G.A.; Nakatsuji, H.; Hada, M.; Ehara, K.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, T.; Nakajima, Y.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J.E.; Hratchian, H.P.; Cross, J.B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R.E.; Yazyev, O.; Austin, A.J.; Cammi, R.; Pomelli, C.; Ochterski, J.; Ayala, P.Y.; Morokuma, K.; Voth, G.A.; Salvador, P.; Dannenberg, J.J.; Zakrzekski, V.G.; Dapprich, S.; Daniels, A.D.; Strain, M.C.; Farkas, O.; Malick, D.K.; Rabuck, A.D.; Raghavachari, K.; Foresman, J.B.; Ortiz, J.V.; Cui, Q.; Baboul, A.G.; Clifford, S.; Cioslowski, J.; Stefanov, B.B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.I.; Martin, R.L.; Fox, D.J.; Keith, T.; Al-Laham, M.A.; Peng, C.Y.; Nanayakkara, A.; Challacombe, M.; Gill, P.M.W.; Johnson, B.G.; Chen, W.; Wong, M.W.; Gonzalez, C.; Pople, J.A. Gaussian 03, revision B.01, Gaussian Inc.: Pittsburgh, PA, 2003.