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Journal of the American Chemical Society
‡School of Chemistry, University of Bristol, Cantock's Close,
Bristol, BS8 1TS, United Kingdom
Department of Chemistry, Swansea University, Singleton
28.
Selinsky, B. S.; Perlman, M. E.; London, R. E.; Unkefer, C.
1
2
3
4
5
6
7
8
9
1
1
1
1
1
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5
5
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5
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5
6
J.; Mitchell, J.; Blakley, R. L., Biochemistry 1990, 29, 1290-1296.
#
29.
Feeney, J., Biochemistry 1993, 32, 6846-6854.
0. Cowart, M.; Falzone, C. J.; Benkovic, S. J., J. Labelled
Comp. Radiopharm. 1994, 34, 67-71.
1. Saeed, M.; Tewson, T. J.; Erdahl, C. E.; Kohen, A., Nucl.
Med. Biol. 2012, 39, 697-701.
Cheung, H. T. A.; Birdsall, B.; Frenkiel, T. A.; Chau, D. D.;
Park, Swansea SA2 8PP, United Kingdom
3
ACKNOWLEDGMENTS
3
We are grateful to Dr James R. Williamson, Scripps Research
Institute, for his gift of prsA. The help of Dr Rob Jenkins and
Mr Thomas Williams with mass spectrometry is gratefully
acknowledged. This work was supported by Cardiff University
through a President’s Research Scholarship to A.A. and the
UK’s Biotechnology and Biological Sciences Research Council
32.
Curthoys, N. P.; Scott, J. M.; Rabinowitz, J. C., J. Biol.
Chem. 1972, 247, 1959-1964.
33.
zymol. 1986, 122, 309-312.
34.
Moran, R. G.; Keyomarsi, K.; Colman, P. D., Methods En-
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
Gräwert, T.; Fischer, M.; Bacher, A., IUBMB Life 2013,
(
BBSRC) through grants BB/J005266/1 and BB/L020394/1 to
65, 310-322.
R.K.A.
35.
Fischer, M.; Thöny, B.; Leimkühler, S., The biosynthesis
of folate and pterins and their enzymology. In Comprehensive
natural products II, Mander, L.; Liu, H.-W., Eds. Elsevier: Oxford,
England, 2010; Vol. 7, pp 599-648.
REFERENCES
36.
Rebelo, J.; Auerbach, G.; Bader, G.; Bracher, A.; Nar, H.;
1.
Hoffbrand, A. V.; Weir, D. G., Br. J. Haematol. 2001, 113,
Hösl, C.; Schramek, N.; Kaiser, J.; Bacher, A.; Huber, R.; Fischer, M.,
J. Mol. Biol. 2003, 326, 503-516.
5
79-589.
2.
3.
Fox, J. T.; Stover, P. J., Vitam. Horm. 2008, 79, 1-44.
Basu, P.; Burgmayer, S. J., Coord. Chem. Rev. 2011, 255,
37.
2358.
38.
5094.
39.
Burg, A. W.; Brown, G. M., J. Biol. Chem. 1968, 243, 2349-
Yim, J. J.; Brown, G. M., J. Biol. Chem. 1976, 251, 5087-
Illarionova, V.; Eisenreich, W.; Fischer, M.; Haussmann,
1
4
1
016-1038.
Schwarz, G.; Mendel, R. R.; Ribbe, M. W., Nature 2009,
60, 839-847.
4.
5.
Thöny, B.; Auerbach, G.; Blau, N., Biochem. J. 2000, 347,
C.; Romisch, W.; Richter, G.; Bacher, A., J. Biol. Chem. 2002, 277,
28841-28847.
-16.
6.
7.
Pfleiderer, W., Adv. Exp. Med. Biol. 1993, 338, 1-16.
Noguchi, Y.; Ishii, A.; Matsushima, A.; Haishi, D.; Yasu-
40.
Schramek, N.; Bracher, A.; Bacher, A., J. Biol. Chem.
2001, 276, 2622-2626.
muro, K.; Moriguchi, T.; Wada, T.; Kodera, Y.; Hiroto, M.; Nishimu-
ra, H.; Sekine, M.; Inada, Y., Mar. Biotechnol. (NY) 1999, 1, 207-
2
41.
Dantola, M. L.; Vignoni, M.; Capparelli, A. L.; Lorente, C.;
Thomas, A. H., Helv. Chim. Acta 2008, 91, 411-425.
10.
42.
son, J. R., ACS Chem. Biol. 2008, 3, 499-511.
43. Tolbert, T. J.; Williamson, J. R., J. Am. Chem. Soc. 1996,
118, 7929-7940.
Schultheisz, H. L.; Szymczyna, B. R.; Scott, L. G.; William-
8.
Ducker, G. S.; Rabinowitz, J. D., Cell Metab. 2017, 25, 27-
Murima, P.; McKinney, J. D.; Pethe, K., Chem. Biol. 2014,
4
2.
9.
21, 1423-1432.
0. Nzila, A.; Ward, S. A.; Marsh, K.; Sims, P. F.; Hyde, J. E.,
Trends Parasitol. 2005, 21, 292-298.
1. Nzila, A.; Ward, S. A.; Marsh, K.; Sims, P. F.; Hyde, J. E.,
Trends Parasitol. 2005, 21, 334-339.
44.
Angelastro, A.; Dawson, W. M.; Luk, Y. P. L.; Allemann, R.
1
K., ACS Catal. 2017, 7, 1025-1029.
45.
Gross, A.; Abril, O.; Lewis, J. M.; Geresh, S.; Whitesides, G.
1
M., J. Am. Chem. Soc. 1983, 105, 7428-7435.
46.
Schoedon, G.; Redweik, U.; Frank, G.; Cotton, R. G.; Blau,
1
2.
13.
662.
4.
Locasale, J. W., Nat. Rev. Cancer. 2013, 13, 572-583.
Yang, M.; Vousden, K. H., Nat. Rev. Cancer 2016, 16, 650-
N., Eur. J. Biochem. 1992, 210, 561-568.
47.
2410.
48.
Suzuki, Y.; Brown, G. M., J. Biol. Chem. 1974, 249, 2405-
1
World Health Organization, WHO Model Lists of Essen-
Gabelli, S. B.; Bianchet, M. A.; Xu, W.; Dunn, C. A.; Niu, Z.
tial Medicines. 19 ed.; 2015.
D.; Amzel, L. M.; Bessman, M. J., Structure 2007, 15, 1014-1022.
49. Mathis, J. B.; Brown, G. M., J. Biol. Chem. 1970, 245,
3015-3025.
1
1
5.
6.
Zhao, R.; Goldman, I. D., Oncogene 2003, 22, 7431-7457.
Müller, I. B.; Hyde, J. E., Mol. Biochem. Parasitol. 2013,
1
88, 63-77.
17. Sköld, O., Sulfonamides and Trimethorpim. In Antimi-
50.
15239.
51.
Wang, Y.; Li, Y.; Yan, H., Biochemistry 2006, 45, 15232-
crobial Drug Resistance, Mayers, D. L., Ed. Humana Press: New
York, 2009; Vol. 1, pp 259-269.
Derrick, J. P., Vitam. Horm. 2008, 79, 411-433.
Weisman, R. A.; Brown, G. M., J. Biol. Chem. 1964, 239,
52.
18.
Copeland, R. A.; Harpel, M. R.; Tummino, P. J., Expert
326-331.
53.
316.
54.
Opin. Ther. Targets 2007, 11, 967-978.
Griffin, M. J.; Brown, G. M., J. Biol. Chem. 1964, 239, 310-
Richey, D. P.; Brown, G. M., Biochim. Biophys. Acta 1970,
1
20.
9.
Cleland, W. W., Arch. Biochem. Biophys. 2005, 433, 2-12.
Vardi-Kilshtain, A.; Nitoker, N.; Major, D. T., Arch. Bio-
chem. Biophys. 2015, 582, 18-27.
222, 237-239.
21.
22.
23.
24.
25.
Cook, P. F., Isotopes Environ. Health Stud. 1998, 34, 3-17.
O'Leary, M. H., Annu Rev Biochem 1989, 58, 377-401.
Wharton, C. W., Nat. Prod. Rep. 2000, 17, 447-453.
Palmer, A. G., Acc. Chem. Res. 2015, 48, 457-65.
55.
Chenault, H. K.; Simon, E. S.; Whitesides, G. M., Biotech-
nol. Genet. Eng. Rev. 1988, 6, 221-270.
56.
Schweitzer, B. I.; Dicker, A. P.; Bertino, J. R., FASEB J.
1990, 4, 2441-2452.
Schramm, V. L., Acc. Chem. Res. 2015, 48, 1032-1039.
57.
Charlton, P. A.; Young, D. W.; Birdsall, B.; Feeney, J.;
26.
Maunder, P.; Finglas, P.; Mallet, A.; Mellon, F.; Razzaque,
Roberts, G. C. K., J. Chem. Soc., Perkin Trans. 1 1985, 1349-1353.
M.; Ridge, B.; Vahteristo, L.; Witthoft, C., J. Chem. Soc., Perkin Trans.
1999, 1311-1323.
7. Cocco, L.; Groff, J. P.; Temple, C.; Montgomery, J. A.; Lon-
don, R. E.; Matwiyoff, N. A.; Blakley, R. L., Biochemistry 1981, 20,
972-3978.
58.
Fierke, C. A.; Johnson, K. A.; Benkovic, S. J., Biochemistry
1
1987, 26, 4085-4092.
2
59.
Shrimpton, P.; Allemann, R. K., Protein Sci. 2002, 11,
1442-1451.
3
60.
Shrimpton, P.; Mullaney, A.; Allemann, R. K., Proteins
2003, 51, 216-223.
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