The Development of Novel Antibiotics Using ... - Jacobs University
The Development of Novel Antibiotics Using ... - Jacobs University
The Development of Novel Antibiotics Using ... - Jacobs University
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List <strong>of</strong> figures and schemes:<br />
Page<br />
Figure 1. 1 H-NMR spectrum for (4R,5R)-1,3-dioxolane-4,5-dicarbohydrazide (2)…………………………5<br />
Figure 2. 13 C-NMR spectrum for (4R,5R)-1,3-dioxolane-4,5-dicarbohydrazide (2)………………………...5<br />
Figure 3. ESI-MS spectrum for (4R,5R)-1,3-dioxolane-4,5-dicarbohydrazide (2)………….………………6<br />
Figure 4. Tandem ESI-MS 2 spectrum for (4R,5R)-1,3-dioxolane-4,5-dicarbohydrazide (2)……..…………6<br />
Figure 5. 1 H-NMR spectrum for (4S,5S)-1,3-dioxolane-4,5-dicarbohydrazide (4)……………………….....6<br />
Figure 6. 13 C-NMR spectrum for (4S,5S)-1,3-dioxolane-4,5-dicarbohydrazide (4)……………………...…7<br />
Figure 7. ESI-MS spectrum for (4S,5S)-1,3-dioxolane-4,5-dicarbohydrazide (4)…………..……………....7<br />
Figure 8. Tandem ESI-MS 2 spectrum for (4S,5S)-1,3-dioxolane-4,5-dicarbohydrazide (4)…………..…….7<br />
Figure 9. 1 H-NMR spectrum for (2R,3R)-2,3-dihydroxy dicarbohydrazide (5)………………..……………8<br />
Figure 10. 13 C-NMR spectrum for (2R,3R)-2,3-dihydroxy dicarbohydrazide (5)………………..………….8<br />
Figure 11. ESI-MS spectrum for (2R,3R)- 2,3-dihydroxy dicarbohydrazide (5)………….……….………..9<br />
Figure 12. Tandem ESI-MS 2 spectrum for (2R,3R)-2,3-dihydroxy dicarbohydrazide (5)……….………….9<br />
Scheme 1. Proposed fragmentation mechanism for (2R,3R)-2,3-dihydroxy dicarbohydrazide (5)….……....9<br />
Figure 13. 1 H-NMR spectrum for (2S,3S)- 2,3-dihydroxy dicarbohydrazide (6)………………..………....10<br />
Figure 14. 13 C-NMR spectrum for (2S,3S)- 2,3-dihydroxy dicarbohydrazide (6)………………..…….….10<br />
Figure 15. ESI-MS spectrum for (2S,3S)-2,3-dihydroxy dicarbohydrazide (6)……………………..……..11<br />
Figure 16. Tandem ESI-MS 2 spectrum for (2S,3S)- 2,3-dihydroxy dicarbohydrazide (6)……….….……..11<br />
Scheme 2. Proposed fragmentation mechanism for (2S,3S)- 2,3-dihydroxy dicarbohydrazide (6)………..11<br />
Optimisation <strong>of</strong> the [2+2]-cyclocondensation reaction<br />
• Figure 17. APCI-TOF MS for macrocycle 7 (ratio <strong>of</strong> hydrazide to dialdehyde is 2:1)...………..…12<br />
• Figure 18. APCI-TOF MS for macrocycle 7 (ratio <strong>of</strong> hydrazide to dialdehyde is 1:2)…...….……12<br />
• Figure 19. APCI-TOF MS for macrocycle 7 (ratio <strong>of</strong> hydrazide to dialdehyde is 1:1)…….……...13<br />
• Figure 20. APCI-TOF MS for macrocycle 7 (ratio <strong>of</strong> hydrazide to dialdehyde is 1.2:1)…….……13<br />
Figure 21. 1 H-NMR spectrum for macrocycle (7)………………………………………………………….14<br />
Figure 22. ESI-MS spectrum for macrocycle (7)……………………...…………………………………...14<br />
Figure 23. Tandem ESI-MS 2 spectrum for macrocycle (7)……..……………………..…………………...14<br />
Figure 24. 1 H-NMR spectrum for macrocycle (8)………………………………………………………….15<br />
Figure 25. ESI-MS spectrum for macrocycle (8)……………………...…………………………………...15<br />
Figure 26. Tandem ESI-MS 2 spectrum for macrocycle (8)………..…………………...…………………..15<br />
Scheme 3. Proposed fragmentation mechanism for macrocycle (8)………………………………………..16<br />
Figure 27. APCI-MS 2 spectrum for macrocycle (9)………………………………………………………..16<br />
Figure 28. APCI-MS 2 spectrum for macrocycle (9)………………………….…………………….……....17<br />
Figure 29. 1 H-NMR spectrum for macrocycle (9)………………………………………………………….17<br />
Figure 30. Tandem APCI-MS 2 spectrum for macrocycle (9)……..……….……………………………….17<br />
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