acetate to wash out sulfur residues and product was obtained
following elution with 5% methanol in ethyl acetate) to afford
acetamide 18 as an oil (360 mg, 70%); a–b ratio approx 2 : 1 ratio
(by integration of the 1H NMR spectrum). dH (400 MHz, CDCl3)
2.08, 2.07, 2.07, 2.06 (12H, 4 × s, 3 × OAc a, 1 × NHAc a) 1.94,
1.95, 2.03, 2.06 (12H, 4 × s, 1 × OAc b, 1 × NHAc b), 3.31–3.38
(1H, m, H-5b), 3.42–3.49 (1H, m, H-5a), 3.56–3.62 (1H, m, H-5ꢀa),
2003, 59, 10239–10248; (c) X. Wen, D. C. Crick, P. J. Brennan and P. G.
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3.66–3.72 (1H, m, H-5ꢀb), 4.02 (1H, dt, J3,4 5.3 Hz, J4,5 5.3 Hz, J4,5
ꢀ
ꢀ
7.8 Hz, H-4b), 4.23 (1H, dt, J3,4 4.8 Hz, J4,5 4.8 Hz, J4,5 6.3 Hz,
H-4a), 4.89 (1H, J2,3 1.7 Hz, dd, H-3a), 5.14 (1H, d, H-2a), 5.21
(1H, dd, J2,3 5.3 Hz, H-3b), 5.28 (1H, dd, J1,2 4.5 Hz, H-2b), 6.08
(1H, s, H-1a), 6.19–6.21 (2H, m, NHa, NHb), 6.31 (1H, d, H-1b);
dC (100.6 MHz, CDCl3) 20.6, 20.7, 21.0 (3 × s, 3 × OAc a), 20.4,
20.8, 21.1 (3 × s, 3 × OAc b), 23.1 (2 × s, NHAc a, NHAc b),
40.7, 42.6 (C5-a, C5-b), 75.4 (C3-b), 75.6 (C2-b), 77.5 (C3-a), 80.6
(C2-a, C4-b), 83.1 (C4-a), 93.6 (C1-a), 99.0 (C1-b), 169.2, 169.4,
=
169.4, 169.7, 170.1, 170.2, 170.4, 170.5 (4 × Ac C O a, 4 × Ac
+
+
+
=
C O b); m/z (ES ) 340 (M + Na , 50%), 376 (M + MeCN/NH4 ,
100%); HRMS (ES+) calculated NaC13H19NO6 340.1003. Found
=
=
340.1003; mmax (thin film) 1748 (s, C O ester), 1660 (s, C O amide),
10 There are some branch points in which further arabinose units are
added onto OH-3.
1547 (s, N-H bending) cm−1.
11 F. Pan, M. Jackson, Y. Ma and M. R. McNeil, J. Bacteriol., 2001, 183,
3991–3998.
Spot culture method for testing of anti-mycobacterial activity
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and 18 were prepared in DMSO at a range of concentrations up to
100 mg mL−1. These stock solutions were added into different wells
of 6-well plates, with 5 lL DMSO alone added to control wells
(0.1% v/v). Molten MB agar (5 mL) containing OADC (oleic acid-
albumin-dextrose-catalase, Difco) was poured immediately into
the wells of the 6-well plates containing the extracts with thorough
mixing. Once solidified, the MB agar containing test reagents and
controls was inoculated with 5 lL of a 105 dilution of a mid-
log phase culture (OD 1.0) of M. bovis BCG Pasteur containing
approximately 500 cells. The cells were allowed to soak onto MB
agar before the plates were covered, sealed with parafilm, inverted
and incubated at 37 ◦C for 7–14 days. The resulting circular
spot cultures were photographed using a BioRad Gel-Doc 2000
system.
Acknowledgements
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We gratefully acknowledge financial support from the Leverhulme
Trust (Postdoctoral Fellowship to I.A.S.).
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