A. M. Socha et al. / Bioorg. Med. Chem. 18 (2010) 7193–7202
7201
(3H, m). 13C NMR (CDCl3, mixture of rotamers) 172.1, 171.8, 171.3,
170.5, 170.2, 168.8, 161.5, 145.4, 140.2, 129.7, 124.8, 123.4, 116.4,
116.1, 113.4, 61.0, 60.3, 57.6, 56.6, 54.2, 53.3, 50.9, 47.5, 47.2, 46.4,
44.4, 40.9, 38.0, 33.9, 33.2, 32.8, 31.9, 30.4, 29.7, 28.9, 28.2, 27.3,
26.2, 25.7, 22.2, 21.7, 18.1, 15.1, 13.9. MS (ESI, m/z): 775.8
[M+Na]+ for C39H53N6O8F.
cation-adjusted Mueller–Hinton broth (SMHB; Difco Laboratories,
Sparks, MD, USA; 25 g/mL calcium and 12.5 g/mL magnesium)
was used to dilute antimicrobial agents in a serial twofold sche-
dule. Colony counts for the inoculum verification were determined
using Tryptic Soy Agar plates (TSA, Difco, Becton Dickinson Co.,
l
l
Sparks, MD, USA). Following incubation, 100 lL of broth was sub-
cultured onto TSA for MBC determination. MIC and MBC determi-
nation can be found in Table 2 and 3. Control isolates were
obtained from the American Type Culture Collection (ATCC) and
were as follows: Methicillin-resistant S. epidermidis (MRSE ATCC
35984); MSSA (ATCC 35556) and, VRE (ATCC 2030).
5.2.6.8. Acyldpesipeptide 10e. Isolated yield from deprotected
peptidolactone: 22.0 mg (0.037 mmol, 37%) white amorphous
powder. 1H NMR (CDCl3, mixture of rotamers) 7.69 (1H, d), 6.99
(1H, d), 7.18 (1H, m), 6.94 (4H, m), 6.75 (1H, m), 5.94 (1H, d),
5.75 (1H, m), 5.58 (1H, m), 5.02 (1H, m), 4.90 (1H, m), 4.80 (2H,
m), 4.62 (2H, m), 4.00 (1H, m), 3.70 (3H, m), 3.60 (2H, m), 3.28
(2H, m), 2.92 (1H, m), 2.60 (1H, m), 2.27 (3H, m), 2.02 (6H, m),
1.86 (5H, m), 1.72 (1H, m), 1.38 (3H, m), 1.30 (4H, m), 0.93 (3H,
m), 0.85 (3H, m). MS (ESI, m/z): 777.4 [M+Na]+ for C39H53N6O8F.
Acknowledgments
Brown University is gratefully acknowledged for financial sup-
port to J.K.S. and A.M.S. K.L.L. was supported by the Rhode Island
VA Hospital. The authors thank Suzanne Woodmansee for perform-
ing the biological assays.
5.2.6.9. Acyldpesipeptide 10f. Isolated yield from deprotected
peptidolactone: 25 mg (0.034 mmol, 34%) white amorphous pow-
der. 1H NMR (CDCl3, mixture of rotamers) 7.52 (1H, d), 7.47 (1H,
d), 7.15 (1H, m), 6.82 (4H, m), 5.90 (1H, d, J = 16 Hz), 5.30 (1H,
d), 4.92 (2H, m), 4.54 (1H, m), 4.40 (1H, m), 4.23, 1H, m), 3.85
(1H, d, J = 12 Hz), 3.58 (3H, m), 3.34 (1H, m), 2.91 (3H, s), 2.85
(1H, m), 2.62 (2H, m), 2.06 (4H, m), 1.98 (4H, m), 1.81 (2H, d),
1.23 (4H, m), 0.85 (3H, m). 13C NMR (CDCl3, mixture of rotamers)
172.4, 172.2, 171.0, 166.6, 161.6, 145.5, 140.2, 129.9, 125.3,
123.3, 116.5, 113.6, 66.8, 61.1, 60.2, 58.0, 56.9, 54.3, 51.2, 47.5,
38.0, 34.2, 32.9, 31.9, 30.3, 29.7, 29.4, 28.6, 28.1, 26.4, 26.2, 25.7,
23.3, 22.7, 22.2, 15.6, 15.3, 14.1, 13.9. MS (ESI, m/z): 761.3
[M+Na]+ for C38H51N6O8F.
Supplementary data
Supplementary data associated with this article can be found, in
References and notes
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5.2.6.11. Acyldpesipeptide 10h. Isolated yield from deprotected
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5.3. Biological assays
Minimum inhibitory concentrations (MIC) were determined in
duplicate using methods outlined by The Clinical and Laboratory
Standards Institute. Compounds were dissolved in DMSO and fresh