The Development of Novel Antibiotics Using ... - Jacobs University

Table 2. High resolution ESI-TOF MS data in the positive ion mode for the intermediates which were detected after
2 h via paths (a) and (b), products appeared as (M+H + , paths a and b) ions
Intermediate Measured m/z Molecular Formula Theoretical m/z Error
[ppm]
13 a,b 399.1285 a [M+H] + C 19 H 18 N 4 O 6 399.1299 3.5
399.1304 b [M+H] + 399.1299 1.3
14 a,b 474.1759 a [M+H] + C 25 H 23 N 5 O 5 474.1772 2.8
474.1769 b [M+H] + 474.1772 0.7
15 a,b 467.1910 a [M+H] + C 24 H 26 N 4 O 6 467.1925 3.2
467.1916 b [M+H] + 467.1925 1.9
16 a,b 571.1903 a [M+H] + C 24 H 26 N 8 O 9 571.1896 ˗1.2
571.1879 b [M+H] + 571.1896 3.0
17 a,b 646.2388 a [M+H] + C 30 H 31 N 9 O 8 646.2368 ˗3.0
646.2356 b [M+H] + 646.2368 1.9
18 a,b 707.3144 a [M+H] + C 34 H 42 N 8 O 9 707.3148 0.5
707.3135 b [M+H] + 707.3148 ˗0.1
19 a,b 607.1806 a [M+H] + C 33 H 26 N 4 O 8 607.1823 2.9
607.1824 b [M+H] + 607.1823 ˗0.1
20 a,b 757.2752 a [M+H] + C 45 H 36 N 6 O 6 757.2769 2.3
757.2761 b [M+H] + 757.2769 1.1
21 a,b 675.2440 a [M+H] + C 38 H 34 N 4 O 8 675.2449 1.3
675.2435 b [M+H] + 675.2449 2.1
22 a,b 682.2280 a [M+H] + C 39 H 31 N 5 O 7 682.2296 2.4
682.2272 b [M+H] + 682.2296 3.6
23 a,b 750.2888 a [M+H] + C 44 H 39 N 5 O 7 750.2922 4.5
750.2924 b [M+H] + 750.2922 ˗0.3
a
Intermediates were detected after 2 h of refluxing dialdehyde and dihydrazide building block precursors 1-4,
b Intermediates were detected after 2 h of refluxing macrocycles 5-7.
Figure 2. Intermediates detected after 2 h of refluxing dihydrazide and dialdehyde precursors 1-4 in DMF/MeOH.
11 | P a g e