Regioselective phosphorylation of carbohydrates and various alcohols by bacterial acid phosphatases; probing the substrate specificity of the enzyme from Shigella flexneri

Advanced Synthesis and Catalysis

Volumn 347, Issue 7-8, 2005, Pages 1155-1162

  Van Herk, Teunie ^a   Hartog, Aloysius F ^a   Van Der Burg, Alida M ^a   Wever, Ron ^a  

^a UNIVERSITY OF AMSTERDAM   (Netherlands)

Author keywords

Enzymatic phosphorylation; Glucose 6 phosphate; Monophosphate; Non specific acid phosphatase; Primary alcohol; Regioselectivity

Indexed keywords

ACID PHOSPHATASE; ALCOHOL DERIVATIVE; BACTERIAL ENZYME; CARBOHYDRATE; GLUCOSE; GLUCOSE 6 PHOSPHATE; INOSINE; INOSINE PHOSPHATE; PHOSPHORUS; PYROPHOSPHATE;

ARTICLE; CATALYSIS; CONTROLLED STUDY; ENZYME SPECIFICITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NONHUMAN; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PHOSPHORYLATION; SALMONELLA ENTERICA; SHIGELLA FLEXNERI;

EID: 20544460638     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200505072     Document Type: Article

References (28)

1. S. Jones, D. Selitsianos, K. J. Thomson, S. M. Toms, J. Org. Chem. 2003, 68, 5211-5216.
2. P. Lemmen, W. Richter, B. Werner, R. Karl, R. Strumpf, I. Ugi, Synthesis 1993, 1-10.
3. L. A. Slotin, Synthesis 1977, 737-752.
4. D. V. Yashunsky, A. V. Nikolaev, J. Chem. Soc. Perkin Trans, 1 2000, 1195-1198.
5. H. K. Chenault, R. F. Mandes, K. R. Hornberger, J. Org. Chem. 1997, 62, 331-336.
6. E. E. Nifantiev, M. K. Grachev, S. Y. Burmistrov, Chem. Rev. 2000, 100, 3755-3799.
7. B. Axelrod, J. Biol. Chem. 1948, 172, 1-13.
8. J. Appleyard, Biochem. J. 1948, 42, 596-597.
9. R. K. Morton, Biochem. J. 1958, 70, 150-155.
10. G. M. Rossolini, S. Schippa, M. L. Riccio, F. Berlutti, L. E. Macaskie, M. C. Thaller, Cell. Mol. Life Sci. 1998, 54, 833-850.
11. J. Stukey, G. M. Carman, Prot. Sci. 1997, 6, 469-472.
12. W. Hemrika, R. Renirie, H. L. Dekker, P. Barnett, R. Wever, Proc. Natl. Acad. Sci. USA 1997, 94, 2145-2149.
13. A. F. Neuwald, Prot. Sci. 1997, 6, 1764-1767.
14. W. Hemrika, R. Renirie, S. Macedo-Ribeiro, A. Messerschmidt, R. Wever, J. Biol. Chem. 1999, 274, 23820-23827.
15. R. Renirie, W. Hemrika, R. Wever, J. Biol. Chem. 2000, 275, 11650-11657.
16. W. J. Arion, B. K. Wallin, P. W. Carlson, A. J. Lange, J. Biol. Chem. 1972, 247, 2558-2565.
17. rd edn., (Ed.: P. D. Boyer), Academic Press, New York, 1972, pp. 543-609.
18. K. Ishikawa, Y. Mihara, N. Shimba, N. Ohtsu, H. Kawasaki, E.-I. Suzuki, Y. Asano, Protein Eng. 2002, 15, 539-543.
19. Y. Asano, Y. Mihara, H. Yamada, J. Mol. Catal. B: Enzymatic 1999, 6, 271-277.
20. Y. Mihara, T. Utagawa, H. Yamada, Y. Asano, Appl. Environ. Microbiol. 2000, 66, 2811-2816.
21. N. Tanaka, Z. Hasan, A. F. Hartog, T. van Herk, R. Wever, Org. Biomol. Chem. 2003, 1, 2833-2889.
22. D. H. Brown, Biochim. Biophys. Acta 1951, 7, 487-493.
23. P. M. Collins, R. J. Ferrier, Monosaccharides. Their chemistry and their roles in natural products, John Wiley and Sons, Chichester, 1995.
24. K. Ishikawa, Y. Mihara, K. Gondoh, E.-I. Suzuki, Y. Asano, EMBO J. 2000, 19, 2412-2423.
25. N. Tanaka, V. Dumay, Q. Liao, A. J. Lange, R. Wever, Eur. J. Biochem. 2002, 269, 2162-2167.
26. A. Pollak, R. L. Baughn, G. M. Whitesides, J. Am. Chem. Soc. 1977, 99, 2366-2367.
27. C.-H. Wong, G. M. Whitesides, J. Am. Chem. Soc. 1981, 103, 4890-4899.
28. E. A. Noltmann, C. J. Gubler, S. A. Kuby, J. Biol. Chem. 1961, 236, 1225-1230.