Biosynthesis of the vancomycin group of antibiotics: Involvement of an unusual dioxygenase in the pathway to (S)-4-hydroxyphenylglycine [2]

Journal of the American Chemical Society

Volumn 122, Issue 22, 2000, Pages 5389-5390

  Choroba, Oliver W ^a   Williams, Dudley H ^a   Spencer, Jonathan B ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOPEPTIDE; TYROSINE AMINOTRANSFERASE; VANCOMYCIN DERIVATIVE;

DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; LETTER; STRUCTURE ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 0034616852     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja000076v     Document Type: Letter

References (23)

1. Neu, H. C. Science 1992, 257, 1064-1073.
2. McCormick, M. H.; Stark, W. M.; Pittenger, G. E.; Pittenger, R. C.; McGuire, J. M. Antibiot. Annu. 1955-56, 606-611.
3. Williams, D. H. Acc. Chem. Res. 1984, 17, 364-369.
4. Williams, D. H.; Kalman, J. R. J. Am. Chem. Soc. 1977, 99, 2768-2774.
5. Sheldrick, G. M.; Jones, P. G.; Kennard, O.; Williams, D. H.; Smith, G. A. Nature 1978, 271, 223-225.
6. Nicolaou, K. C.; Mitchell, H. J.; Jain, N. F.; Winssinger, N.; Hughes, R.; Bando, T. Angew. Chem., Int. Ed. Engl. 1999, 38, 240-244.
7. Evans, D. A.; Wood, M. R.; Trotter, B. W.; Richardson, T. I.; Barrow, J. C.; Katz, J. L. Angew. Chem., Int. Ed. Engl. 1998, 37, 2700-2704.
8. Nicolaou, K. C.; Natarajan, S.; Li, H.; Jain, N. F.; Hughes, R.; Solomon, M. E.; Ramanjulu, J. M.; Boddy, C. N. C.; Takayanagi, M. Angew. Chem., Int. Ed. Engl. 1998, 37, 2708-2714.
9. Nicolaou, K. C.; Jain, N. F.; Natarajan, S.; Hughes, R.; Solomon, M. E.; Li, H.; Ramanjulu, J. M.; Takayanagi, M.; Koumbis, A. E.; Bando, T. Angew. Chem., Int. Ed. Engl. 1998, 37, 2714-2716.
10. Nicolaou, K. C.; Takayanagi, M.; Jain, N. F.; Natarajan, S.; Koumbis, A. E.; Bando, T.; Ramanjulu, J. M. Angew. Chem., Int. Ed. Engl. 1998, 37, 2717-2719.
11. van Wageningen, A. M. A.; Kirkpatrick, P. N.; Williams, D. H.; Harris, B. R.; Kershaw, J. K.; Lennard, N. J.; Jones, M.; Jones, S. J. M.; Solenberg, P. J. Chem. Biol. 1998, 5, 155-162.
12. Solenberg, P. J.; Matsushima, P.; Stack, D. R.; Wilkie, S. C.; Thompson, R. C.; Baltz, R. H. Chem. Biol. 1997, 4, 195-202.
13. Sussmuth, R. D.; Pelzer, S.; Nicholson, G.; Walk, T.; Wohlleben, W.; Jung, G. Angew. Chem., Int. Ed. Engl. 1999, 38, 1976-1979.
14. Hammond, S. J.; Williamson, M. P.; Williams, D. H.; Boeck, L. D.; Marconi, G. G. J. Chem. Soc., Chem. Commun. 1982, 344-346.
15. Lindblad, B.; Lindsledt, G.; Lindsledt, S.; Rundgren, M. J. Biol. Chem. 1977, 252, 5073-5084.
16. Crouch, N. P.; Adlington, R. M.; Baldwin, J. E.; Lee, M. H.; MacKinnon, C. H. Tetrahedron 1997, 53, 6993-7010.
17. The only other dioxygenase identified for which the substrate acts as both the ketoacid and the substrate for hydroxylation is α-ketoisocaproate oxygenase [Sabourin, P. J.; Bieber, L. L. J. Biol. Chem. 1982, 7468-7471].
18. Akthar, M.; Wright, J. N. Nat. Prod. Rep. 1991, 527-551.
19. We have subcloned and expressed ORF 17 and preliminary results show that it catalyzes the formation of (S)-4-hydroxyphenylglycine from 4-hydroxyphenylglyoxalate in the presence of pyridoxal phosphate as a cofactor.
20. 18O [see also: Lindblad, B.; Lindstedt, G.; Lindstedt, S. J. Am. Chem. Soc. 1970, 92, 7446-7449].
21. 2O could occur by nonspecific transfer of one or another of the two hydroxyl ligands in 13 to the organic radical in intermediate 13 (Scheme 4a).
22. (a) Baldwin, J. E.; Adlington, R. M.; Crouch, N. P.; Pereira, I. A. C. Tetrahedron 1993, 49, 7499-7518.
23. (b) Baldwin, J. E.; Adlington, R. M.; Crouch, N. P.; Pereira, I. A. C.; Aplin, R. T.; Robinson, C. J. Chem. Soc., Chem. Commun. 1993, 105-107.