Evidence of benzilic rearrangement during the electrochemical oxidation of D-glucose to D-glucaric acid

Carbohydrate Research

Volumn 346, Issue 4, 2011, Pages 512-518

  Ibert, Mathias ^a   Fuerts, Patrick ^a   Merbouh, Nabyl ^b   Feasson, Christian ^c   Marsais, Francis ^c  

^a Roquette Frres Society   (France)

^b SIMON FRASER UNIVERSITY   (Canada)

^c INSA   (France)

Author keywords

Benzilic rearrangement; Electrochemical oxidation; Maribersonic acid; TEMPO; Tricarboxylic acid

Indexed keywords

FREE RADICALS; GLUCOSE;

2 ,2 ,6 ,6-TETRAMETHYL-1-PIPERIDINYLOXY; ANALYTICAL METHOD; BENZILIC REARRANGEMENT; D-GLUCOSE; GLUCARIC ACID; SIDE PRODUCTS; TEMPO; TRICARBOXYLIC ACIDS;

ELECTROCHEMICAL OXIDATION;

BENZILIC ACID DERIVATIVE; GLUCOSE; MARIBERSONIC ACID; SACCHARIC ACID; TEMPOL; TRICARBOXYLIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL STRUCTURE; ELECTROCHEMISTRY; OXIDATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 79952359848     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2010.12.017     Document Type: Article

References (28)

1. N. Merbouh, J.M. Bobbitt, and C. Bruckner J. Carbohydr. Chem. 21 2002 65 77
2. Merbouh, N.; Bobitt, J. M.; Bruckner, C. US Patent 6,498,269 B1, 2002.
3. N. Merbouh, J.F. Thaburet, M. Ibert, F. Marsais, and J.M. Bobbitt Carbohydr. Res. 336 2001 75 78
4. J.F. Thaburet, N. Merbouh, M. Ibert, F. Marsais, and G. Queguiner Carbohydr. Res. 330 2001 21 29
5. M. Ibert, F. Marsais, N. Merbouh, and C. Bruckner Carbohydr. Res. 337 2002 1059 1063
6. Feasson, C.; Fuertes, P.; Ibert, M.; Marsais, F.; Queguiner, G.; Comini, S.; Grossel, J.-M. US Patent 7728170, 2010.
7. M. Ibert, P. Fuertes, N. Merbouh, C. Fiol-Petit, C. Feasson, and F. Marsais Electrochim. Acta 55 2010 3589 3594
8. K. Freudenberg, and F. Blummel Liebigs Ann. Chem. 440 1924 47 59
9. O.T. Schmidt, and C.C. Weber-Molster Ann. 515 1934 43 65
10. L. Lowendahl, and G. Petersson Anal. Biochem. 72 1976 623 628
11. L. Lowendahl, G. Petersson, and O. Samuelson Acta Chem. Scand. B 29 1975 975 980
12. L. Lowendahl, G. Petersson, and O. Samuelson Acta Chem. Scand. B 1975 526 527
13. L. Lowendahl, and O. Samuelson Acta Chem. Scand. B 30 1976 691 694
14. S. Ekberg, C. Ekberg, and Y. Albinsson J. Solution Chem. 33 2004 465 477
15. B.Y. Yang, and R. Montgomery Carbohydr. Res. 280 1996 47 57
16. Z. Hricoviniova, D. Lamba, and M. Hricovini Carbohydr. Res. 340 2005 455 458
17. Z. Hricoviniova-bilikova, M. Hricovini, M. Petrusova, A.S. Serianni, and L. Petrus Carbohydr. Res. 319 1999 38 46
18. W.A. Szarek, B.M. Pinto, and T.B. Grindley Can. J. Chem. 61 1983 461 469
19. W.A. Szarek, B.M. Pinto, A.H. Haines, and T.B. Grindley Can. J. Chem. 60 1982 390 414
20. T. Matsumoto, M. Yamame, and S. Inoue Chem. Lett. 1984 1819 1822
21. R. Yanagihara, J. Egashira, S. Yoshikawa, and S. Osanai Bull. Chem. Soc. Jpn. 68 1995 237 242
22. R. Yanagihara, S. Osanai, and S. Yoshikawa Chem. Lett. 1992 89 90
23. L. Lindstrom, and O. Samuelson Acta Chem. Scand. B 31 1977 479 484
24. C. Acerete, L. Garrigos, J. Guilleme, E. Diez, and A. Aldas Electrochim. Acta 26 1981 1041 1045
25. K. Niemela J. Chromatogr. 399 1987 235 243
26. K. Niemela, and E. Sjostrom Carbohydr. Res. 144 1985 87 92
27. K. Niemela, and E. Sjostrom Carbohydr. Res. 144 1985 93 99
28. Ibert, M., Doctorate Thesis INSA of Rouen, 2002.