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

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Intens. 4 x10 553.0 6 4 2 0 300 400 500 600 700 800 m/z Figure 62. APCI-MS 2 spectrum for macrocycle (18) from DMSO (positive mode). Intens. 4 x10 276.8 0.8 0.6 0.4 188.7 553.1 162.8 248.8 407.0 0.2 292.9 376.9 465.0 521.0 316.9 0.0 150 200 250 300 350 400 450 500 m/z Figure 63. Tandem APCI-MS 2 spectrum for macrocycle (18) from DMSO (positive mode). Scheme 15. Proposed fragmentation mechanism for macrocycle (17), positve mode. S36
Intens. 4 x10 550.9 3 2 1 0 500 1000 1500 2000 2500 m/z Figure 64. APCI-MS 2 spectrum for macrocycle (18) from DMSO (negative mode). Intens. 6000 274.7 5000 256.7 4000 3000 2000 246.7 292.8 404.9 532.9 551.0 1000 332.8 360.9 386.9 230.6 523.0 0 250 300 350 400 450 500 m/z Figure 65. Tandem APCI-MS 2 spectrum for macrocycle (18) from DMSO (negative mode). HO OH H HN NH N O O N HN N H O OH NH O O N H HN N O OH NH O O N H HN N O OH NH O O N - H -H 2 O N HN O HO O N NH OH N HN O HO O N NH OH N HN O HO O N NH OH H N HN O O N NH OH C 24 H 24 N 8 O 8 m/ z 552 C 23 H 24 N 8 O 8 m/ z 551 C 24 H 21 N 8 O 6 m/ z 533 H O OH HN N NH O O N N N C 20 H 17 N 6 O 4 m/ z 405 Scheme 16. Proposed fragmentation mechanism for macrocycle (18), negative mode. S37
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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
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aimed at assessing molecular recogn
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Paper 7 manuscript Synthesis, self-
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2 Similar to the case of trianglimi
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4 Receptor 7 showed enhanced recogn
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6 The newly synthesized receptors s
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8 27. Nour, H. F.; Hourani, N.; Kuh
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120| P a g e Appendix
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Supplementary Information: Suppleme
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Supplementary Material (ESI) for Or
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Page 145 and 146: 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 and 172: Intens. 7 x10 200.7 1.5 1.0 0.5 0.0
Page 173 and 174: Intens. 4 x10 577.2 2.0 1.5 1.0 451
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: Scheme 14. Proposed fragmentation m
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
Page 223 and 224: Intens. [%] 100 775.3 80 388.1 60 4
Page 225 and 226: Intens. 600 N HN O O 467.1916 400 O
Page 227 and 228: Intens. 6000 5000 HN N O O O O NH N
Page 229 and 230: Table 1. High resolution ESI-TOF da
Page 231 and 232: i Figure 1. 1 H NMR spectrum for ma
Page 233 and 234: i Figure 5. 1 H NMR spectrum for ma
Page 235 and 236: i j Figure 9. 1 H NMR spectrum for
Page 237 and 238: i Figure 13. DEPT-135 spectrum for
Page 239 and 240: Scheme 1. General mechanism of frag
Page 241 and 242: Intens. [%] 100 80 60 40 20 0 O H N
Page 243 and 244: Intens. [%] 100 1131.3 80 60 40 20
Page 245 and 246: 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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