A general enzymatic method for the synthesis of natural and 'unnatural' UDP- and TDP-nucleotide sugars [20]

Journal of the American Chemical Society

Volumn 122, Issue 28, 2000, Pages 6803-6804

  Jiang, Jiqing ^a   Biggins, John B ^a   Thorson, Jon S ^a  

^a Weill Cornell Graduate School of Biomedical Sciences   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

NUCLEOTIDE DERIVATIVE; THYMIDINE DIPHOSPHATE; URIDINE DIPHOSPHATE SUGAR;

CARBOHYDRATE SYNTHESIS; ENZYME SPECIFICITY; GLYCOSYLATION; LETTER; NONHUMAN; SALMONELLA ENTERICA;

EID: 0034686686     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja001444y     Document Type: Letter

References (29)

1. (a) Liu, H.-w.; Thorson, J. S. Annu. Rev. Microbiol. 1994, 48, 223-256.
2. (b) Weymouth-Wilson, A. C. Nat. Prod. Rep. 1997, 14, 99-110.
3. (c) Omura, S., Ed. In Macrolide Antibiotics, Chemistry, Biology and Practice; Academic Press: New York, 1984.
4. (d) Johnson, D. A.; Liu, H.-w. Curr. Opin. Chem. Biol. 1998, 2, 642-649.
5. (e) Trefzer, A.; Salas, J. A.; Bechthold, A. Nat. Prod. Rep. 1999, 16, 283-299.
6. Gal, D-galactose; Glc, D-glucose; Man, D-mannose; NTP, nucleotide triphosphate; pFPTC, pentafluorophenoxythiocarbonyl; TDP, thymidine diphosphate; TMP, thymidine monophosphate; TTP, thymidine triphosphate; UDP, uridine diphosphate.
7. (a) Madduri, K.; Kennedy, J.; Rivola, G.; Inventi-Solari, A.; Filppini, S.; Sanuso, G.; Colombo, A. L.; Gewain, K. M.; Occi, J. L.; MacNeil, D. J.; Hutchinson, C. R. Nature Biotech. 1998, 16, 69-74.
8. (b) Zhao, L.; Ahlert, J.; Xue, Y.; Thorson, J. S.; Sherman, D. H.; Liu, H.-w. J. Am. Chem. Soc. 1999, 121, 9881-9882 and references therein.
9. (a) Zhao, Y.; Thorson, J. S. J. Org. Chem. 1998, 63, 7568-7572.
10. (b) Elhalabi, J. M.; Rice, K. G. Curr. Med. Chem. 1999, 6, 93-116.
11. Altreuter, D. H.; Clark, D. S. Curr. Opin. Biotech. 1999, 10, 130-136.
12. (a) Lindquist, L.; Kaiser, R.; Reeves, P. R.; Lindberg, A. A. Eur. J. Biochem. 1993, 211, 763-770.
13. (b) Gallo, M. A.; Ward J.; Hutchinson, C. R. Microbiol. 1996, 142, 269-275.
14. The gene rm/A was previously known as rfbA (Reeves et al. Trends Microbiol. 1996, 4, 495-502).
15. p was stored in aliquots (-80 °C) until used.
16. The α/β-40 mixture (1:1.5) was chromatographically resolved.
17. Anisuzzaman, A. K. M.; Whistler, R. L. Carbohydr. Res. 1978, 61, 511-518.
18. Reist, E. J.; Spencer, R. R.; Calkins, D. F.; Baker, B. R.; Goodman, L. J. Org. Chem. 1965, 2312-2317.
19. Kanie, O.; Crawley, S. C.; Palcic, M. M.; Hindsgaul, O. Carbohydr. Res. 1993, 243, 139-164.
20. Zhiyuan, Z.; Magnusson, G. Carbohydr. Res. 1994, 262, 79-101.
21. For select compounds, product peaks (ref 15) were lyopholized and submitted directly for HRMS (FAB) analysis.
22. -1). The reaction was incubated with slow agitation for 30 min at 37 °C, quenched with MeOH (50 μL), and centrifuged (5 min, 14000 x g) and the supernatant was stored at -20 °C until analysis by HPLC.
23. 275 nm).
24. These yields might be further optimized by using pyrophosphatase to drive the equilibrium of the reaction (ref 4b).
25. (a) Angyal, S. J. Angew. Chem., Int. Ed. 1969, 8, 157-226.
26. (b) Boons, G.-J. In Carbohydrate Chemistry; Boons, G.-J., Ed.; Thompson Science: Padstow; 1998; pp 1-20.
27. (a) Thorson, J. S.; Shen, B.; Whitwam, R. E.; Liu, W.; Li, Y.; Ahlert, J. Bioorg. Chem. 1999, 27, 172-188.
28. (b) Whitwam, R. E.; Ahlert, J.; Holman, T. R.; Ruppen, M.; Thorson, J. S. J. Am. Chem. Soc. 2000, 122, 1556-1557.
29. (c) Thorson, J. S.; Sievers, E. L.; Ahlert, J.; Shepard, E.; Whitwam, R. E.; Onwueme, K. C.; Ruppen, M. Curr. Pharm. Des. 2000, in press.