Enantioselective reductive amination of α-keto acids to α-amino acids by a pyridoxamine cofactor in a protein cavity

Journal of the American Chemical Society

Volumn 118, Issue 44, 1996, Pages 10702-10706

  Kuang, Hao ^a   Brown, Matthew L ^a   Davies, Ronald R ^a   Young, Eva C ^a   Distefano, Mark D ^a  

^a University of Minnesota   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BINDING PROTEIN; LIPID BINDING PROTEIN; PROTEIN DERIVATIVE; PYRIDOXINE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG DESIGN; GEL FILTRATION; MASS SPECTROMETRY; PROTEIN BINDING; PROTEIN LIPID INTERACTION; PROTEIN STRUCTURE; PROTEIN SYNTHESIS; SPECTROPHOTOMETRY;

EID: 0029798560     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja954271z     Document Type: Article

References (36)

1. Seebach, D. Angew. Chem, Int. Ed. Engl. 1990, 29, 1320.
2. (a) Dugas, H. Bioorganic Chemistry; Springer-Verlag New York, Inc.: New York, 1996.
3. (b) Breslow, R. Acc. Chem. Res. 1995, 28, 146-153.
4. (a) Kaiser, E. T.; Lawrence, D. S. Science 1984, 226, 505-511.
5. (b) Levine, H. L.; Nakagawa, Y.; Kaiser, E. T. Biochem. Biophys. Res. Comm. 1977, 76, 64-70.
6. (c) Corey, D. R.; Schultz, P. G. Science 1987, 238, 1401-1403.
7. Xu, Z.; Bernlohr, D. A.; Banaszak, L. J. Biochemistry 1992, 31, 3484-3492.
8. LaLonde, J. M.; Bernlohr, D. A.; Banaszak, L. J. Biochemistry 1994, 33, 4885-4895.
9. Banaszak, L. J.; Winter, N.; Xu, Z.; Bernlohr, D. A.; Cowan, S.; Jones, T. A. Adv. Protein Chem. 1994, 45, 89-151.
10. (a) Sha, R. S.; Xu, Z.; Banaszak, L. J.; Bernlohr D. A. J. Biol. Chem. 1993, 268, 7885-7892.
11. (b) Stump, D. G.; Lloyd, R. S.; Chytil, F. J. Biol. Chem. 1991, 266, 4622-4630.
12. (c) Jiang, N.; Frieden, C. Biochemistry 1993, 32, 11015-11021.
13. (d) Kim, K.; Cistola, D. P.; Frieden, C. Biochemistry 1996, 35, 7553-7558.
14. (e) Cistola, D. P.; Kim, K.; Rogl, H. Frieden, C. Biochemistry 1996, 35, 7559-7565.
15. Martell, A. E. Acc. Chem. Res. 1989, 22, 115-124.
16. (a) Breslow, R.; Hammond, M.; Lauer, M. J. Am. Chem. Soc. 1980, 102, 421-422.
17. (b) Breslow, R.; Canary, J. W.; Varney, M.; Waddell, S. T.; Yang, D. J. Am. Chem. Soc. 1990, 112, 5121-5219.
18. (c) Cochran, A. G.; Pham, T.; Sugasawara, R.; Schultz, P. G. J. Am. Chem. Soc. 1991, 113, 6672-6673.
19. (d) Imperiali, B.; Roy, R. S. J. Am. Chem. Soc. 1994, 116, 12083-12084.
20. (e) Kikuchi, J.-I.; Zhang, Z. Y.; Murakami, Y. J. Am. Chem. Soc. 1995, 117, 5383-5384.
21. (a) Bruice, T. C.; Topping, R. M. J. Am. Chem. Soc. 1963, 85, 1480-1487.
22. (b) Bruice, T. C.; Topping, R. M. J. Am. Chem. Soc. 1963, 85, 1488-1492.
23. (c) Thanassi, J. W.; Butler, A. R.; Bruice, T. C Biochemisty 1965, 4, 1463-1470.
24. Modification of this residue with bulky reagents blocks the binding of fatty acids: (a) Buelt, M. K.; Bernlohr, D. A. Biochemistry 1990, 29, 7408-7413. (b) Buelt, M. K.; Xu, Z.; Banaszak, L. J.; Bernlohr, D. A. Biochemistry 1992, 31, 3493-3499. Alkylation of thiols positioned in the cavity with fluorophores generates highly fluorescent derivatives: (c) Frieden, C.; Jiang, N.; Cistola, D. P. Biochemistry 1995, 34, 2724-2730. Both of these observations are consistent with modifications within the cavity.
25. Modification of this residue with bulky reagents blocks the binding of fatty acids: (a) Buelt, M. K.; Bernlohr, D. A. Biochemistry 1990, 29, 7408-7413. (b) Buelt, M. K.; Xu, Z.; Banaszak, L. J.; Bernlohr, D. A. Biochemistry 1992, 31, 3493-3499. Alkylation of thiols positioned in the cavity with fluorophores generates highly fluorescent derivatives: (c) Frieden, C.; Jiang, N.; Cistola, D. P. Biochemistry 1995, 34, 2724-2730. Both of these observations are consistent with modifications within the cavity.
26. Modification of this residue with bulky reagents blocks the binding of fatty acids: (a) Buelt, M. K.; Bernlohr, D. A. Biochemistry 1990, 29, 7408-7413. (b) Buelt, M. K.; Xu, Z.; Banaszak, L. J.; Bernlohr, D. A. Biochemistry 1992, 31, 3493-3499. Alkylation of thiols positioned in the cavity with fluorophores generates highly fluorescent derivatives: (c) Frieden, C.; Jiang, N.; Cistola, D. P. Biochemistry 1995, 34, 2724-2730. Both of these observations are consistent with modifications within the cavity.
27. Banks, B. E. C.; Diamantis, A. A.; Vernon, C. A. J. Chem. Soc. 1961, 4135-4247.
28. (a) Lindroth, P.; Mopper, K. Anal. Chem, 1979, 51, 1667-1674.
29. (b) Nimura, N.; Kinoshita, T. J. Chromatogr. 1986, 352, 169-177.
30. (c) Buck, R. H.; Krummen, K. J. Chromatogr. 1987, 387, 255-265.
31. We have also prepared a conjugate of ALBP containing a Cu(II) phenanthroline moiety within the cavity. This protein catalyzes the enantioselective hydrolysis of amino acid esters.
32. Xu, Z.; Buelt, M. K.; Banaszak, L. J.; Bernlohr, D. A. J. Biol. Chem. 1991, 266, 14367-14370.
33. Breslow, R.; Czarnik, A. W.; Lauer, M.; Leppkes, R.; Winkler, J.; Zimmerman, S. J. Am. Chem. Soc. 1986, 108, 1969-1979.
34. Bradford, M. M. Anal. Biochem. 1976, 72, 248-254.
35. Riddles, P. W.; Blakeley, R. L.; Zerner, B. Methods Enzymol. 1983, 91, 49-59.
36. Metzler, D. E.; Snell, E. E. J. Am. Chem. Soc. 1952, 74, 979-980.