Kinetics and mechanism of allantoin racemization

Bioorganic Chemistry

Volumn 28, Issue 2, 2000, Pages 62-72

  Kahn, Kalju ^a   Tipton, Peter A ^a  

^a University of Missouri   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLANTOIN; SOLVENT;

ARTICLE; CATALYSIS; ENANTIOMER; ENZYME ACTIVITY; KINETICS; NUCLEAR MAGNETIC RESONANCE; PH; PRIORITY JOURNAL; PROTON TRANSPORT; RACEMIC MIXTURE;

EID: 0033914814     PISSN: 00452068     EISSN: None     Source Type: Journal    
DOI: 10.1006/bioo.2000.1162     Document Type: Article

References (26)

1. Reynolds P. H. S., Boland M. J., Blevins D. G., Randall D. D., Schubert K. R. Trends Biol. Sci. 1982;366-368.
2. Voet D., Voet J., Pratt C. W. Fundamentals of Biochemistry. 1999;Wiley, New York.
3. Kahn K., Serfozo P., Tipton P. A. J. Am. Chem. Soc. 119:1997;5435-5442.
4. Modric N., Derome A. E., Ashcroft S. J. H., Poje M. Tet. Lett. 33:1992;6691-6694.
5. Kahn K. Kinetic and Mechanistic Characterization of the Urate Oxidase Reaction. 1998;University of Missouri.
6. Lee K. W., Roush A. H. Arch. Biochem. Biophys. 108:1964;460-467.
7. Reist M., Carrupt P.-A., Testa B., Lehmann S., Hansen J. J. Helv. Chim. Acta. 79:1996;767-778.
8. The numbering of the carbon atoms for allantoin is shown in Scheme 2. (S)-Allantoin is shown as the reactant.
9. Titherley A. W. J. Chem. Soc. 103:1913;1336-1338.
10. Canellakis E. S., Cohen P. P. J. Biol. Chem. 213:1955;385-395.
11. Abblard J., Meynaud A. Bull. Soc. Chim. Fr. 3:1971;942-946.
12. Cram D. J. Blomquist A. T. Fundamentals of Carbanion Chemistry. 1965;85-113 Academic Press, New York.
13. Vogels G. D., de Windt F. E., Bassie W. Rec. Trav. Chim. 88:1969;940-950.
14. Mootz D. Acta Cryst. 19:1965;726-734.
15. Fischer E., Ach F. Berichte. 32:1899;2721-2749.
16. Horseradish peroxidase was used to oxidize 7-methylallantoin, and the resulting product, 3-methylallantoin, was observed to undergo facile proton exchange at C5. K. Kahn, unpublished observations.
17. Sarma A. D., Serfozo P., Kahn K., Tipton P. A. J. Biol. Chem. 274:1999;33863-33865.
18. Kahn K., Tipton P. A. Biochemistry. 37:1998;11651-11659.
19. 's-Gravenmade E. J., Vogels G. D., van Pelt C. Rec. Trav. Chim. 88:1969;929-939.
20. Eberstadt M., Gemmecker G., Mierke D. F., Kessler H. Angew. Chem. Int. Ed Engl. 34:1995;1671-1695.
21. Evans J. N. S. Biomolecular NMR Spectroscopy. 1995;Oxford Univ. Press, Oxford.
22. Hansen P. E. Prog. Nucl. Magn. Reson. Spectrosc. 14:1981;175-296.
23. Kao L.-F., Barfield M. J. Am. Chem. Soc. 107:1985;2323-2330.
24. Clark M., Cramer R. D. III, Van Opdenbosch N. J. Comp. Chem. 10:1989;982-1012.
25. Dewar M. J. S., Zoebisch E. G., Healy E. F., Stewart J. J. P. J. Am. Chem. Soc. 107:1985;3902-3909.
26. Frisch M. J., Trucks G. W., Schlegel H. B., Gill P. M. W., Johnson B. G., Robb M. A., Cheeseman J. R., Keith T., Petersson G. A., Montgomery J. A., Raghavachari K., Al-Laham M. A., Zakrzewski V. G., Ortiz J. V., Forseman J. B., Cioslowski J., Stefanov B. B., Nanayakkara A., Challacombe M., Peng C. Y., Ayala P. Y., Chen W., Wong M. W., Andres J. L., Replogle E. S., Gomperts R., Martin R. L., Fox D. J., Binkley J. S., Defrees D. J., Baker J., Stewart J. P., Head-Gordon M., Gonzalez C., Pople J. A. Gaussian 94. 1995;Gaussian, Pittsburgh.