´
C. Guerardet al. / Bioorg. Med. Chem. Lett. 14 (2004) 1661–1664
1664
3. (a) Grogan, D. W.; Cronan, J. E. Microb. Mol. Biol.
(Wallac) scintillation fluid were added and the radioactivity
counted (Rackbeta, LKB, Sweeden).
Reviews 1997, 61, 429. (b) Barry, C. E.; Lee, R. E.;
Mdluli, K.; Sampson, A. E.; Schroeder, B. G.; Slayden,
R. A.; Yuan, Y. Prog LipidRes. 1998, 37, 143.
4. (a) Pohl, S.; Law, J. H.; Ryhage, R. Biochim. Biophys.
Acta 1963, 70, 583. (b) Polacheck, J. W.; Tropp, B. E.;
Law, J. W. J. Biol. Chem. 1966, 241, 3362. (c) Law, J. H.
Acc. Chem. Res. 1970, 4, 199.
5. Cronan, J. E.; Nunn, W. D.; Batchelor, J. G. Biochimi.
Biophys. Acta 1974, 348, 63.
6. Lederer, E. Q. Rev. 1969, 23, 453.
15. Taylor, F. R.; Cronan, J. E. Biochemistry 1979, 18, 3292.
16. (a) Coward, J. K.; Anderson, G. L.; Tang, K.-C. Methods
Enzymol. 1983, 94, 286. (b) Ramalingam, K.; Woodard,
R. W. Carbohydr. Res. 1985, 142, 123. (c) Francesconi,
K. A.; Edmonds, J. S.; Stick, R. V. J. Chem. Soc., Perkin
Trans 1 1992, 1349.
17. Selected data for compound 6 de=0%: 1H NMR (D2O) d
8.18 (s, 1H, C8H), 8.05 (s, 1H, C2H), 6.00 (d, J=5.2Hz,
0 0 0
1H, C1 H), 4.95 (m, 1H, C2 H), 4.47 (m, 2H, C3 H and
C4 H), 3.45 (m, 2H, C5 H), 2.75 (s, 3H, CH3). 13C NMR
(D2O) d 154.8 (C6), 152.1 (C2),0 148.0 (C4), 139.7 and
139.4 (C8), 118.2(C5), 87.8 (C1 ), 77.9 and 77.3 (C40),
72.4 (C20 and C30), 55.7 and 54.1 (C50), 37.0 and 36.5
(CH3). ESI [m/z 314 (M+H+); {calcd for
C11H15N5O4S+H+} 314].
0
0
7. (a) Cohen, T.; Herman, G.; Chapman, T. M.; Kuhn, D.
J. Am. Chem. Soc. 1974, 96, 5627. (b) Buist, P. H.;
MacLean, D. B. Can. J. Chem. 1980, 59, 828. (c)
Buist, P. H.; MacLean, D. B. Can. J. Chem. 1981, 60,
371.
8. Huang, C. C.; Smith, C. V.; Glickman, M. S.; Jacobs,
W. R., Jr.; Sacchettini, J. C. J. Biol. Chem. 2002, 277,
11559.
1
18. Selected data for compound 7: H NMR (D2O) d 8.24 (s,
1H, C8H), 8.19 (s, 1H, C2H), 6.02(d, J=5.2Hz, 1H,
0 0 0
C1 H), 5.15 (m, 1H, C2 H), 4.49 (m, 1H, C4 H), 4.39 (m,
9. Glickman, M. S.; Cox, J. S.; Jacobs, W. R. Mol. Cell
2000, 5, 717.
1H, C3 H), 3.75 (m, 2H, C5 H), 2.96 (s, 3H, CH3). 13C
NMR (D2O) d 155.2 (C6), 152.1 (C2), 148.5 (C4), 140.0
(C8), 112.5 (C5), 88.2 (C10), 77.8 (C40), 72.3 and 71.8 (C20
and C30), 55.9 (C50), 41.0 (CH3).
0
0
10. (a) Taylor, F. R.; Grogan, D. W.; Cronan, J. E. Methods
Enzymol. 1981, 71, 133. (b) Wang, A.-Y.; Grogan, D. W.;
Cronan, J. E. Biochemistry 1992, 31, 11020.
11. Boyle, P. H.; Davis, A. P.; Dempsey, K. J.; Hosken, G. D.
Tetrahedron: Asymmetry 1995, 6, 2819.
19. (a) Kuhn, R.; Jahn, W. Chem. Ber. 1965, 98, 1699. (b)
Borchardt, R. T.; Wu, Y. S. J. Med. Chem. 1974, 17, 862.
1
12. Anderson, G. L.; Bussolotti, D. L.; Coward, J. K. J. Med.
Chem. 1981, 24, 1271.
20. Selected data for compound 8 de=10%: H NMR (D2O)
0
d 8.13 (s, 1H, C8H), 8.06 (s, 1H, C2H), 5.95 (s, 1H, C1 H),
1
0 0
4.95 (m, 1H, C2 H), 4.45 (m, 1H, C4 H), 4.39 (m, 1H,
13. Selected data for compound 4: H NMR (D2O) d 8.35 (s,
0
2H, aromatic), 6.15 (d, J=25.2 Hz, 1H, C1 H), 4.95 (m,
0
0
C3 H), 3.61 (m, 1H, CaH), 3.35 (m, 2H, C5 H), 2.95 (m,
2H, CgH), 2.11 (m, 2H, CbH). 13C NMR (D2O) d 175.4
(COOH), 155.9 (C6), 153.2(C2), 149.1 (C4), 140.5 (C8),
0
1H, C2 H), 4.55 (m, 2H, C3 H and C4 H), 3.90 (m, 2H,
0
0
0
C5 H), 2,95 (s, 3H, CH3), 2.90 (s, 3H, CH3). ESI [m/z 312
0
(M+); {calcd for C12H18N5O3S+} 312].
119.4 (C5), 88.7 (C10), 78.8 and 78.3 (C40), 73.2(C2 and
14. The assay mixture (0.1 mL final volume) consisted of the
following components: 20 mM potassium phosphate buf-
fer, pH 7.4; 0.1 mg of a phospholipide dispersion (pre-
pared as in reference 10); S-[methyl-3H]-adenosyl-l-
methionine at a final specific activity of 25 mCi/mmol,
variable concentration; inhibitor at variable concen-
tration; and 3 mg of purified CFAS (purified as in refer-
ence 10, with modifications). Incubations were carried out
for 15 min at 37 ꢁC, and the reaction was stopped by
adding 1 mL of Cl3CCOOH (10% w/v). The entire reac-
tion mixture was filtreted onto a 2.5 cm glass fiber filter
disk (Whatman GF/A). The filter disks were washed twice
with 1 mL Cl3COOH (10% w/v) and 3 times with 1 mL
of water. After drying, the filter disks were transferred to
a scintillation vial, and 3 mL of Optiphase HighSafe
C30), 54.2and 54.0 (C5 0 and Ca), 47.5 (Cg), 25.1 (Cb). ESI
[m/z 401 (M+H+); {calcd for C14H20N6O6S+H+} 401].
21. Balicki, R. Synth. Commun. 1999, 29, 2235.
1
22. Selected data for compound 9: H NMR (D2O) d 8.19 (s,
0
2H, C8H and C2H), 6.05 (s, 1H, C1 H), 4.95 (m, 1H,
0
C2 H), 4.65 (m, 1H, C4 H), 4.45 (m, 1H, C3 H), 4.02(m,
0
0
0
1H, CaH), 3.75 (m, 2H, C5 H), 3.35 (m, 2H, CgH), 2.27
(m, 2H, CbH). ESI [m/z 417 (M+H+); {calcd for
C14H20N6O7S+H+} 417].
23. Micetich, R. G.; Betageri, S.; Singh, R.; Payne, P. J. Org.
Chem. 1987, 52, 915.
24. Borchardt, R. T.; Pugh, C. S. G. Biochemistry 1982, 21,
1535.
25. Smith, D. D.; Norton, S. J. Biochem. Biophys. Res. Com-
mun. 1980, 94, 1458.