Selective modifications of hydrophobic vitamin B 12 derivatives at c -and d -positions

Journal of Organic Chemistry

Volumn 76, Issue 16, 2011, Pages 6806-6812

  Proinsias, Keith Ó ^a   Giedyk, MacIej ^a   Loska, Rafał ^a   Chromiński, Mikołaj ^a   Gryko, Dorota ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDIC CONDITIONS; DIAMIDES; FUNCTIONALIZED; LACTONE MOIETY; REACTION CONDITIONS; RING OPENING; SELECTIVE MODIFICATION; VITAMIN B;

AMINO ACIDS;

ACID; AMINO ACID; CYANOCOBALAMIN; CYANOCOBALAMIN DERIVATIVE; DIAMIDE; LACTONE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; DECOMPOSITION; HYDROPHOBICITY; MOLECULE; RING OPENING; SENSITIVITY ANALYSIS;

AMINO ACIDS; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; DIAMIDE; LACTONES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; SENSITIVITY AND SPECIFICITY; STEREOISOMERISM; VITAMIN B 12;

EID: 80051732292     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo201235b     Document Type: Article

References (29)

1. Ideas in Chemistry and Molecular Science: Where Chemistry Meets Life; Pignataro, B., Ed.; Wiley-VCH: Weinhem, 2010; pp 95-109.
2. Brown, K. L. Chem. Rev. 2005, 105, 2075-2150
3. Petrus, A. K.; Fairchild, T. J.; Doyle, R. P. Angew. Chem., Int. Ed. 2009, 48, 1022-1028
4. Fedosov, N. S.; Fedosova, N. U.; Kräutler, B.; Next, E.; Peterson, T. E. Biochemistry 2007, 46, 6446-6458
5. Wuerges, J.; Garau, G.; Geremia, S.; Fedosov, S. N.; Pertersen, T. E.; Randaccio, L. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 4386-4391
6. Chalasani, K. B.; Russell-Jones, G. J.; Jain, A. K.; Diwan, P. V.; Jain, S. K. J. Controlled Release 2007, 122, 141-150
7. Bagnato, J. D.; Eilers, A. L.; Horton, R. A.; Grissom, C. B. J. Org. Chem. 2004, 69, 8987-8996
8. Russell-Jones, G. J.; McEwan, J. F. US Patent US006150341A, 2000.
9. Ohno, T.; Ogawa, A.; Hisaeda, Y.; Murakami, Y. J. Chem. Soc., Perkin Trans. 2 1994, 2, 2271-2273
10. Jabbar, Md. A.; Shimakoshi, H.; Hisaeda, Y. Chem. Commun. 2007, 1653-1655
11. Murakami, Y.; Hisaeda, Y. Bull. Chem. Soc. Jpn. 1985, 2652-2658
12. Shimakoshi, H.; Inaoka, T.; Hisaeda, Y. Tetrahedron. Lett. 2003, 44, 6421-6224
13. Wilson, S.; Reinerd, K. S.; Gao, X. US Patent US0066561 A1, 2007.
14. Otten, T.; Dabre, T.; Cosnier, S.; Lusia, A.; Correia, J.; Keese, R. Helv. Chim. Acta 1998, 81, 1117-1126
15. Russell-Jones, G.; Westwood, S.; Farnworth, R.; Findlay, J.; Burger, H. Bioconjugate Chem. 1995, 6, 34-42
16. Pfammatter, M. J.; Dabre, T.; Keese, R. Helv. Chim. Acta 1998, 1105-1116
17. Shimakoshi, H.; Tokunaga, M.; Kuroiwa, K.; Kimizuka, N.; Hisaeda, Y. Chem. Commun. 2004, 50-51
18. Mayor, M.; Scheffold, R. Helv. Chim. Acta 1997, 1183-1189
19. ó Proinsias, K.; Sessler, J. L.; Kurcoń, S.; Gryko, D. Org. Lett. 2010, 12, 4674-4677
20. Van Staveren, D. R.; Waibel, R.; Mundwiler, S.; Schubiger, P. A.; Alberto, R. J. Organomet. Chem. 2004, 689, 4803-4810
21. Van Staveren, D. R.; Mundwiler, S.; Hoffmanns, U.; Pak, J. K.; Spingler, B.; Metzler-Notle, N.; Alberto, R. J. Organomet. Chem. 2004, 689, 4803-4810
22. Pathane, P. M.; Wilbur, D. S.; Heusser, S.; Quadros, E. V.; McLoughlin, P.; Morgan, A. C. Bioconjugate Chem. 1996, 7, 217-232
23. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 14, 2596-2599
24. Amblard, F.; Cho, J. H.; Schinazi, R. F. Chem. Rev 2009, 109, 4207-4220
25. Smeltzer, C. C.; Cannon, M. J.; Pinson, P. R.; Munger, J. D.; West, F. G.; Grissom, C. B. Org. Lett. 2001, 3, 799-801
26. Lee, M.; Grissom, C. B. Org. Lett. 2009, 11, 2499-2502
27. Wei, X.; Chen, W.; Chen, X.; Russell, T. P. Macromolecules 2010, 43, 6234-6236
28. Chan, T. R.; Hilgraf, R.; Sharpless, K. B.; Folkin, V. V. Org. Lett. 2004, 6, 2853-2855
29. Petrus, A. K.; Vortherms, A. R.; Fairchlid, T. J.; Doyle, R. P. Chem. Med. Chem. 2007, 2, 1717-1721