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Chemical Science
exchange HPLC analysis. Briey, each reaction mixture was 15 E. W. C. Sewell, M. P. Pereira and E. D. Brown, J. Biol. Chem.,
treated to 0.5 M NaOH for 25 min at 37 ꢁC. The reaction
2009, 284, 21132–21138.
mixtures were neutralized with the addition of 0.5 M HCl prior 16 S. E. Allison, M. A. D'Elia, S. Arar, M. A. Monteiro and
to anion exchange HPLC analysis. For WTA lability experiments, E. D. Brown, J. Biol. Chem., 2011, 286, 23708–23716.
these reactions underwent further treatment in 1 N HCl for 3 17 Y.-H. Zhang, C. Ginsberg, Y. Yuan and S. Walker,
hours at 100 ꢁC (ref. 35) prior to anion exchange HPLC analysis.
Biochemistry, 2006, 45, 10895–10904.
18 M. S. Trent, J. Biol. Chem., 2001, 276, 43122–43131.
19 P. D. Rick, H. Mayer, B. A. Neumeyer, S. Wolski and D. Bitter-
Suermann, J. Bacteriol., 1985, 162, 494–503.
Acknowledgements
20 A. Bouhss, A. E. Trunkeld, T. D. H. Bugg and D. Mengin-
Lecreulx, FEMS Microbiol. Rev., 2008, 32, 208–233.
21 L. Masson and B. E. Holbein, J. Bacteriol., 1985, 161, 861–867.
We thank Dr Kalinka Koteva and Dr Mehdi Keramane for
assistance during chemical synthesis. We also thank Soumaya
Zlitni and Dr Sebastian Gehrke for helpful discussions in the
preparation of this manuscript. We are grateful for the guidance
provided by Dr Eean Breukink for the preparation of unde-
caprenyl phosphate. Support to EDB for this work included a
salary award (Canada Research Chair) and an operating grant
from the Canadian Institutes of Health Research (MOP-15496).
This work was also supported by National Science Foundation
Major Research Instrumentation Award 1039659 to TAG.
´
22 H. Barreteau, S. Magnet, M. El Ghachi, T. Touze, M. Arthur,
D. Mengin-Lecreulx and D. Blanot, J. Chromatogr. B, 2009,
877, 213–220.
23 Y. J. Lee, A. Ishiwata and Y. Ito, Tetrahedron, 2009, 65, 6310–
6319.
24 E. Breukink, H. E. van Heusden, P. J. Vollmerhaus,
E. Swiezewska, L. Brunner, S. Walker, A. J. R. Heck and
B. de Kruijff, J. Biol. Chem., 2003, 278, 19898–19903.
25 E. Swiezewska, W. Sasak, T. Mankowski, W. Jankowski,
T. Vogtman, I. Krajewska, J. Hertel, E. Skoczylas and
T. Chojnacki, Acta Biochim. Pol., 1994, 41, 221–260.
26 N. K. Khidyrova and K. M. Shakhidoyatov, Chem. Nat.
Compd., 2002, 38, 107–121.
Notes and references
1 A. L. Koch, Clin. Microbiol. Rev., 2003, 16, 673–687.
2 H. W. Boucher, G. H. Talbot, J. S. Bradley, J. E. Edwards,
D. Gilbert, L. B. Rice, M. Scheld, B. Spellberg and 27 L. L. Danilov, T. N. Druzhinina, N. A. Kalinchuk,
J. Bartlett, Clin. Infect. Dis., 2009, 48, 1–12.
3 M. M. Burger and L. Glaser, J. Biol. Chem., 1964, 239, 3168–
3177.
4 F. C. Neuhaus and J. Baddiley, Microbiol. Mol. Biol. Rev.,
2003, 67, 686–723.
5 L. Glaser and M. M. Burger, J. Biol. Chem., 1964, 239, 3187–
3191.
6 E. W. Sewell and E. D. Brown, J. Antibiot., 2014, 67, 43–51.
7 M. A. D'Elia, K. E. Millar, T. J. Beveridge and E. D. Brown, J.
Bacteriol., 2006, 188, 8313–8316.
S. D. Maltsev and V. N. Shibaev, Chem. Phys. Lipids, 1989,
51, 191–203.
28 M. M. Sim, H. Kondo and C. H. Wong, J. Am. Chem. Soc.,
1993, 115, 2260–2267.
29 A. Holkenbrink, D. C. Koester, J. Kaschel and D. B. Werz, Eur.
J. Org. Chem., 2011, 2011, 6233–6239.
30 R. Woodward, W. Yi, L. Li, G. Zhao, H. Eguchi, P. R. Sridhar,
H. Guo, J. K. Song, E. Motari, L. Cai, P. Kelleher, X. Liu,
W. Han, W. Zhang, Y. Ding, M. Li and P. G. Wang, Nat.
Chem. Biol., 2010, 6, 418–423.
8 C. Weidenmaier, J. F. Kokai-Kun, S. A. Kristian, 31 A. P. Bhavsar, R. Truant and E. D. Brown, J. Biol. Chem., 2005,
T. Chanturiya, H. Kalbacher, M. Gross, G. Nicholson, 280, 36691–36700.
B. Neumeister, J. J. Mond and A. Peschel, Nat. Med., 2004, 32 A. Zapun, J. Philippe, K. A. Abrahams, L. Signor, D. I. Roper,
10, 243–245.
E. Breukink and T. Vernet, ACS Chem. Biol., 2013, 8, 2688–
9 C. Weidenmaier, A. Peschel, Y.-Q. Xiong, S. A. Kristian,
2696.
¨
K. Dietz, M. R. Yeaman and A. S. Bayer, J. Infect. Dis., 2005, 33 C. Schaffer, T. Wugeditsch, P. Messner and C. Whiteld,
191, 1771–1777.
Appl. Environ. Microbiol., 2002, 68, 4722–4730.
10 M. L. Atilano, J. Yates, M. Glittenberg, S. R. Filipe and 34 J. W. Schertzer, J. Biol. Chem., 2003, 278, 18002–18007.
P. Ligoxygakis, PLoS Pathog., 2011, 7, e1002421.
35 N. Kojima, Y. Araki and E. Ito, J. Bacteriol., 1985, 161, 299–306.
11 S. Brown, G. Xia, L. G. Luhachack, J. Campbell, 36 J. W. Schertzer and E. D. Brown, J. Bacteriol., 2008, 190, 6940–
T. C. Meredith, C. Chen, V. Winstel, C. Gekeler, 6947.
J. E. Irazoqui, A. Peschel and S. Walker, Proc. Natl. Acad. 37 D. S. Badurina, M. Zolli-Juran and E. D. Brown, Biochim.
Sci. U. S. A., 2012, 109, 18909–18914. Biophys. Acta, 2003, 1646, 196–206.
12 M. A. Farha, A. Leung, E. W. Sewell, M. A. D'Elia, S. E. Allison, 38 B. Soldo, V. Lazarevic, H. M. Pooley and D. Karamata, J.
L. Ejim, P. M. Pereira, M. G. Pinho, G. D. Wright and
E. D. Brown, ACS Chem. Biol., 2013, 8, 226–233.
13 C. Ginsberg, Y.-H. Zhang, Y. Yuan and S. Walker, ACS Chem.
Biol., 2006, 1, 25–28.
Bacteriol., 2002, 184, 4316–4320.
39 L. V. Collins, S. A. Kristian, C. Weidenmaier, M. Faigle,
K. P. Van Kessel, J. A. Van Strijp, F. Gotz, B. Neumeister
and A. Peschel, J. Infect. Dis., 2002, 186, 214–219.
14 M. P. Pereira, J. W. Schertzer, M. A. D'Elia, K. P. Koteva, 40 M. L. Atilano, P. M. Pereira, J. Yates, P. Reed, H. Veiga,
D. W. Hughes, G. D. Wright and E. D. Brown,
ChemBioChem, 2008, 9, 1385–1390.
M. G. Pinho and S. R. Filipe, Proc. Natl. Acad. Sci. U. S. A.,
2010, 107, 18991–18996.
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