Molecular recognition of artificial single-electron acceptor cosubstrates by glucose oxidase?

Journal of the American Chemical Society

Volumn 118, Issue 28, 1996, Pages 6788-6789

  Alzari, Pedro ^b   Anicet, Nathalie ^a   Bourdillon, Christian ^b   Moiroux, Jacques ^a   Savéant, Jean Michel ^a  

^a UNIVERSITÉ PARIS DIDEROT   (France)

^b UNIVERSITÉ DE TECHNOLOGIE DE COMPIÈGNE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

GLUCOSE OXIDASE;

ARTICLE; ENZYME BINDING; ENZYME SPECIFICITY; MODEL; THERMODYNAMICS;

EID: 0029933604     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja960197o     Document Type: Article

References (20)

1. (a) Université Denis Diderot, (b) Université de Compiègne.
2. Bourdillon, C.; Demaille, C.; Moiroux, J.; Savéant, J..-M. J. Am. Chem. Soc. 1993, 115, 2.
3. (a) Lowe, H. J.; Clark, W. M. J. Biol. Chem. 1956, 221, 993.
4. (b) Hemmerich, P.; Veeger, C.; Wood, H. C. S. Angew. Chem., Int. Ed. Engl. 1965, 4, 671.
5. (c) Janik, B.; Elving, P. J. Chem. Rev. 1968, 68, 295.
6. (d) Williams, R. F.; Bruice, T. C. J. Am. Chem. Soc. 1976, 98, 7752.
7. (e) Williams, R. F.; Shinkai, S. S.; Bruice, T. C. J. Am., Chem. Soc. 1977, 99, 921.
8. (c) Eberlein, G.; Bruice, T. C. J. Am., Chem. Soc. 1982, 104, 1449.
9. (f) Stankovich, M. T.; Shopfer, L. M.; Massey, V. J. Biol. Chem. 1978, 253, 4971.
10. (g) Ghisla, S.; Massey, V. Eur. J. Biochem. 1989, 181, 1.
11. (a) As shown in Figure 1 of ref 4b, the catalytic cyclic voltammetric response obtained with (S)-N,N-dimethyl-1-ferrocenylethylamine was found to be about twice the response obtained with the (R) enantiomer.
12. (b) Marx-Tibbon, S.; Katz, E.; Willner, I. J. Am. Chem. Soc. 1995, 117, 9925.
13. 2 Overnight mutarotation of the glucose solutions was particularly important for obtaining reproducible results. The ferrocenium concentrations were calibrated by comparison with solutions of ferrocene methanol of known concentrations. (S)- and (R)- N,N-dimethyl-1-ferrocenylethylamine were purchased from Aldrich and used as received. Glucose was purchased from Prolabo and A. niger glucose oxidase from Boehringer Mannheim (grade I),
14. 5OH; optical path, 1 dm; Perkin Elmer 241 polarimeter). A. niger glucose oxidase from SIGMA (type X-S) was used in this case.
15. (a) Hetch, H. J.; Kalisz, H. M.; Hendle, J.; Schmid, R. D.; Schomburg, D. J. Mol. Biol. 1993, 229, 153.
16. (b) Code PDB:1GAL. Bernstein, F. C.; Koetze, T. F.; Williams, G. F. B.; Meyer, E. F.; Brice, M. D.; Rodgers, J. R.; Kennard, O.; Shimanouchi, P. T.; Tasumi, M. J. Mol. Biol. 1977, 112, 535.
17. Ohsawa, Y.; Aoyagui, S. J. Electroanal. Chem. 1982, 136, 353.
18. 2
19. (a) Marcus, R. A.; Sutin, N. Biophys. Biochim. Acta 1985, 811, 265.
20. (b) Savéant, J-M. Single Electron Transfer and Nucleophilic Substitution. In Advances in Physical Organic Chemistry; Bethel, D., Ed.; Academic Press: New York, 1990; Vol, 26, pp 1-130.