Total synthesis of polyprenyl N-Glycolyl Lipid II as a mycobacterial transglycosylase substrate

Organic Letters

Volumn 13, Issue 19, 2011, Pages 5306-5309

  Meng, Fan Chun ^a   Chen, Kuo Ting ^a,b   Huang, Lin Ya ^a,c   Shih, Hao Wei ^a   Chang, Han Hui ^a   Nien, Fu Yao ^d   Liang, Pi Hui ^b   Cheng, Ting Jen R ^a   Wong, Chi Huey ^a   Cheng, Wei Chieh ^a  

^a GENOMICS RESEARCH CENTER   (Taiwan)

^b NATIONAL TAIWAN UNIVERSITY   (Taiwan)

^c ACADEMIA SINICA   (Taiwan)

^d NATIONAL CHENG KUNG UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOLIPID; GLYCOSYLTRANSFERASE;

ARTICLE; CHEMISTRY; ENZYME SPECIFICITY; METABOLISM; MYCOBACTERIUM TUBERCULOSIS;

GLYCOLIPIDS; GLYCOSYLTRANSFERASES; MYCOBACTERIUM TUBERCULOSIS; SUBSTRATE SPECIFICITY;

EID: 80054762741     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol2021687     Document Type: Article

References (32)

1. Chopra, P.; Meena, L. S.; Singh, Y. Indian J. Med. Res. 2003, 117, 1-9.
2. Johnson, R.; Streicher, E. M.; Louw, G. E.; Warren, R. M.; Helden, P. D. v.; Victor, T. C. Curr. Issues Mol. Biol. 2006, 8, 97-112.
3. Cole, S. T.; Brosch, R.; Parkhill, J.; Garnier, T.; Churcher, C.; Harris, D.; Gordon, S. V.; Eiglmeier, K.; Gas, S.; Barry, C. E.; Tekaia, F.; Badcock, K.; Basham, D.; Brown, D.; Chillingworth, T.; Connor, R.; Davies, R.; Devlin, K.; Feltwell, T.; Gentles, S.; Hamlin, N.; Holroyd, S.; Hornsby, T.; Jagels, K.; Krogh, A.; McLean, J.; Moule, S.; Murphy, L.; Oliver, K.; Osborne, J.; Quail, M. A.; Rajandream, M. A.; Rogers, J.; Rutter, S.; Seeger, K.; Skelton, J.; Squares, R.; Squares, S.; Sulston, J. E.; Taylor, K.; Whitehead, S.; Barrell, B. G. Nature 1998, 393, 537-544.
4. Patru, M.-M.; Pavelka, M. S., Jr. J. Bacteriol. 2010, 192, 3043-3054.
5. Hett, E. C.; Chao, M. C.; Rubin, E. J. PLoS Pathog. 2010, 6, e1001020.
6. Bhakta, S.; Basu, J. Biochem. J. 2002, 361, 635-639.
7. Lepage, S.; Dubois, P.; Ghosh, T.; Joris, B.; Mahapatra, S.; Kundu, M.; Basu, J.; Chakrabarti, P.; Cole, S.; Nguyen-Disteche, M.; Ghuysen, J. J. Bacteriol. 1997, 179, 4627-4630.
8. Goffin, C.; Ghuysen, J.-M. Microbiol. Mol. Biol. Rev. 2002, 66, 702-738.
9. Chambers, H.; Moreau, D.; Yajko, D.; Miick, C.; Wagner, C.; Hackbarth, C.; Kocagoz, S.; Rosenberg, E.; Hadley, W.; Nikaido, H. Antimicrob. Agents Chemother. 1995, 39, 2620-2624.
10. Anishetty, S.; Pulimi, M.; Pennathur, G. Comput. Biol. Chem. 2005, 29, 368-378.
11. Barry, C. E.; Crick, D. C.; McNeil, M. R. Infect. Disord.: Drug Targets 2007, 7, 182-202.
12. Vollmer, W.; Holtje, J.-V. Antimicrob. Agents Chemother. 2000, 44, 1181-1185.
13. Ye, X.-Y.; Lo, M.-C.; Brunner, L.; Walker, D.; Kahne, D.; Walker, S. J. Am. Chem. Soc. 2001, 123, 3155-3156.
14. Halliday, J.; McKeveney, D.; Muldoon, C.; Rajaratnam, P.; Meutermans, W. Biochem. Pharmacol. 2006, 71, 957-967.
15. Crick, D. C.; Mahapatra, S.; Brennan, P. J. Glycobiology. 2001, 11, 107R-118R.
16. Mahapatra, S.; Yagi, T.; Belisle, J. T.; Espinosa, B. J.; Hill, P. J.; McNeil, M. R.; Brennan, P. J.; Crick, D. C. J. Bacteriol. 2005, 187, 2747-2757.
17. Kaur, D.; Brennan, P. J.; Crick, D. C. J. Bacteriol. 2004, 186, 7564-7570.
18. Vollmer, W. FEMS Microbiol. Rev. 2008, 32, 287-306.
19. Raymond, J. B.; Mahapatra, S.; Crick, D. C.; Pavelka,M. S. J. Biol. Chem. 2005, 280, 326-333.
20. Daryaee, F.; Kobarfard, F.; Khalaj, A.; Farnia, P. Eur. J. Med. Chem. 2009, 44, 289-295.
21. Li, K.; Kurosu, M. Heterocycles. 2008, 76, 455-469.
22. Khidyrova, N. K.; Shakhidoyatov, K. M. Chem. Nat. Compd. 2002, 38, 107-121.
23. Ruiz-Rodriguez, A.; Bronze, M.-R.; Ponte, M. N. d. J. Supercrit. Fluids 2008, 45, 171-176.
24. Schwartz, B.; Markwalder, J. A.; Wang, Y. J. Am. Chem. Soc. 2001, 123, 11638-11643.
25. Liu, C.-Y.; Guo, C.-W.; Chang, Y.-F.; Wang, J.-T.; Shih, H.- W.; Hsu, Y.-F.; Chen, C.-W.; Chen, S.-K.; Wang, Y.-C.; Cheng, T.-J. R.; Ma, C.; Wong, C.-H.; Fang, J.-M.; Cheng, W.-C. Org. Lett. 2010, 12, 1608-1611.
26. Stachyra, T.; Dini, C.; Ferrari, P.; Bouhss, A.; van Heijenoort, J.; Mengin-Lecreulx, D.; Blanot, D.; Biton, J.; Le Beller, D. Antimicrob. Agents Chemother. 2004, 48, 897-902.
27. Van Nieuwenhze, M. S.; Mauldin, S. C.; Zia-Ebrahimi, M.; Winger, B. E.; Hornback, W. J.; Saha, S. L.; Aikins, J. A.; Blaszczak, L. C. J. Am. Chem. Soc. 2002, 124, 3656-3660.
28. Benakli, K.; Zha, C.; Kerns, R. J. J. Am. Chem. Soc. 2001, 123, 9461-9462.
29. Chen, Q.; Cheng, Q. Y.; Zhao, Y. C.; Han, B.-H. Macromol. Rapid Commun. 2009, 30, 1651-1655.
30. de Kruijff, B.; van Dam, V.; Breukink, E. Prostaglandins, Leukotrienes Essent. Fatty Acids 2008, 79, 117-21.
31. Shih, H.-W.; Chen, K.-T.; Chen, S.-K.; Huang, C.-Y.; Cheng, T.-J. R.; Ma, C.; Wong, C.-H.; Cheng, W.-C. Org. Biomol. Chem. 2010, 8, 2586-2593.
32. The studies of transformations are in the Supporting Information.