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

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Optimisation of the [2+2]-cyclocondensation reaction Intens. 4 x10 479.2 2.0 1.5 507.2 1.0 577.2 0.5 451.2 519.2 609.2 637.2 0.0 349.1 649.3 491.2 547.2 361.2 389.2 419.2 623.2 677.3 534.2 707.3 735.2 350 400 450 500 550 600 650 700 750 m/z Figure 17. APCI-TOF MS from DMSO (macrocycle 7, reaction was conducted in DMF in the presence of few drops of AcOH, ratio of hydrazide to dialdehyde is 2:1, positive mode). Intens 423.1 8000 HN N O O R R NH O O N 6000 O O 553.2 4000 2000 0 609.2 663.5 741.5 200 400 600 800 1000 1200 1400 m/z Figure 18. APCI-TOF MS from DMSO (macrocycle 7, reaction was conducted in DMF in the presence of few drops of AcOH, ratio of hydrazide to dialdehyde is 1:2, positive mode). S12
Intens. 4 x10 577.2 2.0 1.5 1.0 451.2 0.5 0.0 312.3 340.4 391.3 419.1 437.2 479.2 521.2 563.2 623.2 609.2 647.5 663.4 707.2 741.5 350 400 450 500 550 600 650 700 750 m/z Figure 19. APCI-TOF MS from DMSO (macrocycle 7, reaction was conducted in MeOH in the presence of few drops of AcOH, ratio of hydrazide to dialdehyde is 1:1, positive mode). Intens. 5 x10 4 599.2 3 2 1 0 250 500 750 1000 1250 1500 1750 2000 2250 m/z Figure 20. APCI-TOF MS from DMSO (macrocycle 7, reaction was conducted in MeOH in the presence of few drops of AcOH, ratio of hydrazide to dialdehyde is 1.2:1, positive mode). S13
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The Development of Novel Antibiotic
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Declaration of Authorship I, Hany N
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Abstract Over the past few decades,
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Chapter 2 Trianglimine Chemistry
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Figure 2.4 Trianglimines 10-12 with
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Abbreviations ACN AcOH Ala Acetonit
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RMS ROESY SjGST TFA THF TLC TMS TOC
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Introduction complete remodel of th
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Introduction following protonation.
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Introduction Lehn and co-workers re
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Introduction Figure 1.8 Generation
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Introduction Figure 1.11 Synthetic
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Introduction Figure 1.13 Generation
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Introduction 1.3.11 Boronic ester e
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Introduction References 1. E. Mouli
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Introduction 51. B. Shi, M. F. Grea
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Introduction Figure 2.2 shows compu
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Introduction incorporate β-cyclode
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Introduction Trianglamine-Zn(R) 2 c
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Introduction 24. J. Gajewy, J. Gawr
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Scope of Work Scope of Work In this
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Scope of Work can be obtained from
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Scope of Work Figure 3.4 Structures
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Scope of Work References 1. G. Wrig
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Organic & Biomolecular Chemistry Ci
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Downloaded by Jacobs University Bre
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View Online Downloaded by Jacobs Un
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Paper 2 Rapid Commun. Mass Spectrom
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Trianglimine formation mechanism by
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Paper 3 Org. Biomol. Chem., 2012, 1
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View Online Table 2 Distances (Å)
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Paper 4 Chem. Eur. J., 2012, submit
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(4R,5R)- and (4S,5S)-dimethyl-2,2-d
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that two distinct conformational is
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the thimble was recharged with fres
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Paper 5 Rapid Commu. Mass Spectrom.
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INTRODUCTION No single class of dru
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EXPERIMENTAL All the solvents and r
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(b) Refluxing macrocycles 5, 6 and
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Scheme 1. Graphical representation
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Figure 1. A plot of relative intens
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In contrast, formation of library m
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Figure 5. Generated dynamic library
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macrocycle 32 from the dynamic libr
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The polar carbamate group participa
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[2] WHO World health report 2003. h
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[32] B. Lienard, N. Selevsek, N. Ol
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FULL PAPER Synthesis and ESI-MS Com
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ability of the technique to provide
Page 121 and 122: aimed at assessing molecular recogn
Page 123 and 124: Paper 7 manuscript Synthesis, self-
Page 125 and 126: 2 Similar to the case of trianglimi
Page 127 and 128: 4 Receptor 7 showed enhanced recogn
Page 129 and 130: 6 The newly synthesized receptors s
Page 131 and 132: 8 27. Nour, H. F.; Hourani, N.; Kuh
Page 133 and 134: 120| P a g e Appendix
Page 135 and 136: Supplementary Information: Suppleme
Page 137 and 138: Supplementary Material (ESI) for Or
Page 153 and 154: Monitoring the [3+3]-cyclocondensat
Page 155 and 156: Monitoring the cyclocondensation re
Page 157 and 158: Product ions appeared as [M+H] + Fi
Page 159 and 160: Scheme 1. Assigned higher oligomers
Page 161 and 162: Supplementary Information: Synthesi
Page 163 and 164: Scheme 4. Proposed fragmentation me
Page 165 and 166: DMSO Figure 1. 1 H-NMR spectrum for
Page 167 and 168: Figure 6. 13 C-NMR spectrum for (4S
Page 169 and 170: Intens. 7 x10 1.5 200.7 1.0 0.5 0.0
Page 171: Intens. 7 x10 200.7 1.5 1.0 0.5 0.0
Page 175 and 176: HN N O O R R NH O O N N HN R O O O
Page 177 and 178: Intens. 5 x10 727.2 2.0 1.5 1.0 O O
Page 179 and 180: Intens. 5 x10 697.1 1.5 1.0 728.2 0
Page 181 and 182: O O O O HN N O O NH N HN N O O NH N
Page 183 and 184: Figure 38. 1 H-NMR spectrum for mac
Page 185 and 186: Intens. 5000 276.8 4000 3000 2000 1
Page 187 and 188: Intens. 7 x10 599.1 1.5 1.0 0.5 0.0
Page 189 and 190: (a) HN N O O NH O O N (b) HN N O NH
Page 191 and 192: Scheme 11. Proposed fragmentation m
Page 195 and 196: Scheme 14. Proposed fragmentation m
Page 197 and 198: Intens. 4 x10 550.9 3 2 1 0 500 100
Page 199 and 200: Figure 68. 2D-ROESY spectrum for ma
Page 201 and 202: Supplementary Information: Novel sy
Page 203 and 204: Intens. 6 x10 0.8 0.6 0.4 240.9 459
Page 205 and 206: Figure 9. 1 H-NMR spectrum for macr
Page 209 and 210: Intens. 5 x10 1.5 968.1 1.0 0.5 813
Page 211 and 212: Intens. 5 x10 897.4 4 2 335.3 707.3
Page 213 and 214: Scheme 3. Suggested fragmentation m
Page 217 and 218: Molecular modelling data for the co
Page 219 and 220: Figure 1. 1 H NMR spectrum for dica
Page 221 and 222: Intens. 2000 1493.6091 Host-Guest 1
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Intens. [%] 100 775.3 80 388.1 60 4
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Intens. 600 N HN O O 467.1916 400 O
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Intens. 6000 5000 HN N O O O O NH N
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Table 1. High resolution ESI-TOF da
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i Figure 1. 1 H NMR spectrum for ma
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i Figure 5. 1 H NMR spectrum for ma
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i j Figure 9. 1 H NMR spectrum for
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i Figure 13. DEPT-135 spectrum for
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Scheme 1. General mechanism of frag
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Intens. [%] 100 80 60 40 20 0 O H N
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Intens. [%] 100 1131.3 80 60 40 20
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Intens. 1500 1528.6088 1000 500 150
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Intens. [%] 100 80 60 40 Free guest
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Intens. 4 x10 1085.3575 1.25 1.00 0
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Intens. [%] 100 80 Free guest 586.1
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Synthesis, self-assembly and ESI-MS
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O O HN NH HN O O NH HN O 11 O NH O
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O O HN NH HN O O NH HN O 9 O NH O O
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H 2 O DMSO DMSO Figure 6. 1 H-NMR a
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Intens. 5 x10 5 -MS 487.1588 4 3 2
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Intens. -MS 6 x10 0.8 0.6 0.4 0.2 1
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Intens. -MS 6 x10 O O 350.9 1.5 1.0
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Intens. [%] 100 -MS 486.9 Exact str
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Intens. [%] -MS 100 486.9 80 60 975
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Intens. [%] +MS 100 80 517.2 Exact
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Intens. [%] 100 80 60 +MS 388.1 775
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Intens. [%] 100 +MS 517.2 Exact str
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Intens. [%] 100 80 +MS 1031.4939 7
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Intens. [%] 100 +MS 517.2 Exact str
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Intens. [%] 100 -MS 2 586.1 80 60 4
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Intens. [%] 100 -MS 2 875.2 Exact s
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Table 1. High resolution ESI-TOF/MS
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274 | P a g e
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276 | P a g e
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4. H. Nour, A. López-Periago, N. K
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