Vitamin B12 mimics having a peptide backbone and tuneable coordination and redox properties

Angewandte Chemie - International Edition

Volumn 49, Issue 30, 2010, Pages 5178-5180

  Zhou, Kai ^a   Zelder, Felix ^a  

^a UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

Bioinorganic chemistry; Coordination chemistry; Electrochemistry; Peptides; Vitamins

Indexed keywords

BIOINORGANIC CHEMISTRY; COORDINATION CHEMISTRY; DIMETHYLBENZIMIDAZOLE; MACROCYCLES; METAL CENTERS; PEPTIDE BACKBONES; REDOX PROPERTY; VITAMIN B;

BIOCHEMISTRY; COORDINATION REACTIONS; ELECTROCHEMISTRY; NUTRITION; PEPTIDES;

VITAMINS;

BIOMIMETIC MATERIAL; CYANOCOBALAMIN; DRUG DERIVATIVE; PEPTIDE;

ARTICLE; CHEMICAL STRUCTURE; OXIDATION REDUCTION REACTION; SYNTHESIS;

BIOMIMETIC MATERIALS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PEPTIDES; VITAMIN B 12;

EID: 77954856697     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201001928     Document Type: Article

References (28)

1. 12Proteins, Wiley-VCH, Weinheim, 1998.
2. K. L. Brown, Chem. Rev. 2005, 105, 2075.
3. 12, 1st ed., WileyInterscience, New York, 1999.
4. R. Banerjee, C. Gherasim, D. Padovani, Curr. Opin. Chem. Biol. 2009, 13, 484.
5. J. Kim, C. Gherasim, R. Banerjee, Proc. Natl. Acad. Sci. USA 2008, 105, 14551.
6. I. Mellman, H. F. Willard, P. Youngdahlturner, L. E. Rosenberg, J. Biol Chem. 1979, 254, 1847.
7. J. P. Lerner-Ellis, J. C. Tirone, P. D. Pawelek, C. Dore, J. L. Atkinson, D. Watkins, C. F. Morel, T. M. Fujiwara, E. Moras, A. R. Hosack, G. V. Dunbar, H. Antonicka, V. Forgetta, C. M. Dobson, D. Leclerc, R. A. Gravel, E. A. Shoubridge, J. W. Coulton, P. Lepage, J. M. Rommens, K. Morgan, D. S. Rosenblatt, Nat. Genet 2006, 38, 93.
8. 12 (Ed. : J. M. Pratt), Academic Press, New York, 1972, p. 44.
9. L. Hannibal, C. A. Smith, D. W. Jacobsen, N. E. Brasch, Angew. Chem. 2007, 119, 5232;
10. Angew. Chem. Int. Ed. 2007, 46, 5140.
11. H. A. Hassanin, L. Hannibal, D. W. Jacobsen, M. F. El-Shahat, M. S. A. Hamza, N. E. Brasch, Angew. Chem. 2009, 121, 9071;
12. Angew. Chem. Int. Ed. 2009, 48, 8909.
13. P. Butler, M. O. Ebert, A. Lyskowski, K. Gruber, C. Kratky, B. Kräutler, Angew. Chem. 2006, 118, 1004;
14. Angew. Chem. Int. Ed. 2006, 45, 989.
15. T. Toraya, A. Ishida, J. Biol. Chem. 1991, 266, 5430.
16. R. B. Wang, B. C. MacGillivray, D. H. Macartney, Dalton Trans. 2009, 3584.
17. A. Eschenmoser, Angew. Chem. 1988, 100, 5;
18. Angew. Chem. Int. Ed. Engl. 1988, 27, 5;
19. F. Kreppelt, PhD Thesis, Dissertation no. 9458, ETH-Zürich, 1991.
20. G. Müller, O. Müller, Z. Naturforsch. B 1966, 21, 1159.
21. See the Supporting Information.
22. P. E. Nielsen, M. Egholm, R. H. Berg, O. Buchardt, Science 1991, 254, 1497.
23. U. Diederichsen, H. W. Schmitt, Angew. Chem. 1998, 110, 312;
24. Angew. Chem. Int. Ed. 1998, 37, 302.
25. P. E. Nielsen, Acc. Chem. Res. 1999, 32, 624.
26. G. K. Mittapalli, K. R. Reddy, H. Xiong, O. Munoz, B. Han, F. De Riccardis, R. Krishnamurthy, A. Eschenmoser, Angew. Chem. 2007, 119, 2522;
27. Angew. Chem. Int. Ed. 2007, 46, 2470.
28. The structural formula of 6 is shown in the Supporting Information.