Base-catalyzed decarboxylation of mandelylthiamin: Direct formation of bicarbonate as an alternative to formation of CO2

Journal of the American Chemical Society

Volumn 134, Issue 51, 2012, Pages 20621-20623

  Howe, Graeme W ^a   Bielecki, Michael ^a   Kluger, Ronald ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

BASE CATALYSIS; DECARBOXYLATION REACTIONS; GENERAL BASE CATALYSIS; TRANSITION STATE;

CARBOXYLATION; CATALYSIS; CHEMICAL COMPOUNDS; DISSOCIATION;

CARBON DIOXIDE;

BICARBONATE; BRONSTED BASE; CARBON; CARBON DIOXIDE; CARBOXYLIC ACID; MANDELYLTHIAMIN; THIAMINE DERIVATIVE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CATALYSIS; CATALYST; DECARBOXYLATION; DISSOCIATION; PROTON TRANSPORT; REACTION ANALYSIS;

EID: 84871604651     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja310952a     Document Type: Article

References (30)

1. Guthrie, J. P. Bioorg. Chem. 2002, 30, 32
2. Jencks, W. P. Catalysis in Chemistry and Enzymology; McGraw-Hill: New York, 1969; pp 116-120.
3. Sauers, C. K.; Jencks, W. P.; Groh, S. J. Am. Chem. Soc. 1975, 97, 5546
4. Kluger, R.; Ikeda, G.; Hu, Q. Y.; Cao, P. P.; Drewry, J. J. Am. Chem. Soc. 2006, 128, 15856
5. Cram, D. J.; Haberfield, P. J. Am. Chem. Soc. 1961, 83, 2354
6. Kluger, R.; Mundle, S. O. C. Adv. Phys. Org. Chem. 2010, 44, 357
7. Mundle, S. O. C.; Rathgeber, S.; Lacrampe-Couloume, G.; Sherwood Lollar, B.; Kluger, R. J. Am. Chem. Soc. 2009, 131, 11638
8. Gao, J.; Major, D. T. J. Chem. Theory Comput. 2007, 3, 949
9. Gonzalez-James, O. M.; Singleton, D. A. J. Am. Chem. Soc. 2010, 132, 6896
10. Roca, M.; Pascual-Ahuir, J.; Tunon, I. J. Am. Chem. Soc. 2012, 134, 10509
11. Mundle, S. O. C.; Kluger, R. J. Am. Chem. Soc. 2009, 131, 11674
12. Mundle, S. O. C.; Lacrampe-Couloume, G.; Sherwood Lollar, B.; Kluger, R. J. Am. Chem. Soc. 2010, 132, 2430
13. Vandersteen, A. A.; Mundle, S. O. C.; Kluger, R. J. Org. Chem. 2012, 77, 6505
14. Cheng, X. L.; Wang, J. H.; Tang, K.; Liu, Y. J.; Liu, C. B. Chem. Phys. Lett. 2010, 496, 36
15. Zhang, X. H.; Geng, Z. Y.; Wang, Y. C. Sci. China, Ser. B: Chem. 2011, 54, 762
16. Hu, Q. Y.; Kluger, R. J. Am. Chem. Soc. 2002, 124, 14858
17. Bruning, M.; Berheide, M.; Meyer, D.; Golbik, R.; Bartunik, H.; Liese, A.; Tittmann, K. Biochemistry 2009, 48, 3258
18. Brandt, G. S.; Kneen, M. M.; Petsko, G. A.; Ringe, D.; McLeish, M. J. J. Am. Chem. Soc. 2010, 132, 438
19. Edsall, J. T.; Wyman, J. Biophysical Chemistry; Academic Press: New York, 1958; Chapter 10.
20. Stefanidis, D.; Jencks, W. P. J. Am. Chem. Soc. 1993, 115, 6045
21. Hine, J.; Koser, G. F. J. Org. Chem. 1971, 36, 3591
22. Kemp, D. S.; Paul, K. G. J. Am. Chem. Soc. 1975, 97, 7305
23. Gao, J. L. J. Am. Chem. Soc. 1995, 117, 8600
24. Lin, A. C.; Chiang, Y.; Dahlberg, D. B.; Kresge, A. J. J. Am. Chem. Soc. 1983, 105, 5380
25. Kluger, R.; Moore, I. F. J. Am. Chem. Soc. 2000, 122, 6145
26. Silberstein, H. Ber. Dtsch. Chem. Ges. 1884, 17, 2660
27. Goldschmidt, H.; Bräuer, R. Ber. Dtsch. Chem. Ges. 1906, 39, 109
28. Paulsen, P. J.; Cooke, W. D. Anal. Chem. 1963, 35, 1560
29. Kluger, R. J. Org. Chem. 1964, 29, 2045
30. Bigeleisen, J.; Allen, T. L. J. Chem. Phys. 1951, 19, 760