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Introduction 25. K. Nicolaou, R. Hughes, S. Cho, N. Winssinger, H. Labischinski, R. Endermann, Chem. Eur. J., 2001, 7, 3824. 26. L. Vial, J. Sanders, S. Otto, New J. Chem., 2005, 29, 1001. 27. L. Vial, R. Ludlow, J. Leclaire, R. Pérez-Fernández, S. Otto, J. Am. Chem. Soc., 2006, 128, 10253. 28. B. Danieli, A. Giardini, G. Lesma, D. Passarella, B. Peretto, A. Sacchetti, A. Silvani, G. Pratesi, F. Zunino, J. Org. Chem., 2006, 71, 2848. 29. B. Brisig, J. Sanders, S. Otto, Angew. Chem. Int. Ed., 2003, 42, 1270. 30. T. Hotchkiss, H. Kramer, K. Doores, D. Gamblin, N. Oldham, B. Davis, Chem. Commun., 2005, 4264. 31. O. Ramström, J.-M. Lehn, ChemBioChem., 2000, 1, 41. 32. F. Cougnon, H. Au-Yeung, G. Pantoş, J. Sanders, J. Am. Chem. Soc., 2011, 133, 3198. 33. S. Otto, R. Furlan, J. Sanders, Science, 2002, 297, 590. 34. S. Otto, S. Kubik, J. Am. Chem. Soc., 2003, 125, 7804. 35. A. Kieran, A. Bond, A. Belenguer, J. Sanders, Chem. Commu., 2003, 2674. 36. P. Corbett, L. Tong, J. Sanders, S. Otto, J. Am. Chem. Soc., 2005, 127, 8902. 37. P. Corbett, J. Sanders, S. Otto, J. Am. Chem. Soc., 2005, 127, 9390. 38. K. R. West, K. D. Bake, S. Otto, Org. Lett., 2005, 7, 2615. 39. S. Otto, R. L. E. Furlan, J. K. M. Sanders, J. Am. Chem. Soc., 2000, 122, 12063. 40. B. Fuchs, A. Nelson, A. Star, J. F. Stoddart, S. Vidal, Angew. Chem., 2003, 115, 4352. 41. D. Berkovich-Berger, N. Lemc<strong>of</strong>f, Chem. Commun., 2008, 1686. 42. R. Cacciapaglia, S. Di Stefano, L. Mandolini, J. Am. Chem. Soc., 2005, 127, 13666. 43. R. Cacciapaglia, S. Di Stefano, L. Mandolini, Chem. Eur. J., 2006, 12, 8566. 44. J. A. Berrocal, R. Cacciapaglia, S. Di Stefano, Org. Biomol. Chem., 2011, 9, 8190. 45. J. A. Berrocal, R. Cacciapaglia, S. Di Stefano, L. Mandolini, New J. Chem., 2012, 36, 40. 46. R. Larsson, O. Ramström, Eur. J. Org. Chem., 2006, 285. 47. R. Larsson, Z. Pei, O. Ramström, Angew. Chem. Int. Ed., 2004, 43, 3716. 48. S. J. Rowan, J. K. M. Sanders, J. Org. Chem., 1998, 63, 1536. 49. P. Wipf, S. G. Mahler, K. Okumura, Org. Lett., 2005, 7, 4483. 50. B. Shi, R. Stevenson, D. J. Campopiano, M. F. Greaney, J. Am. Chem. Soc., 2006, 128, 8459. 17 | P a g e
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Page 1 and 2: The Development of Novel Antibiotic
Page 3 and 4: Declaration of Authorship I, Hany N
Page 5 and 6: Abstract Over the past few decades,
Page 7 and 8: Chapter 2 Trianglimine Chemistry
Page 9 and 10: Figure 2.4 Trianglimines 10-12 with
Page 11 and 12: Abbreviations ACN AcOH Ala Acetonit
Page 13 and 14: RMS ROESY SjGST TFA THF TLC TMS TOC
Page 15 and 16: Introduction complete remodel of th
Page 17 and 18: Introduction following protonation.
Page 19 and 20: Introduction Lehn and co-workers re
Page 21 and 22: Introduction Figure 1.8 Generation
Page 23 and 24: Introduction Figure 1.11 Synthetic
Page 25 and 26: Introduction Figure 1.13 Generation
Page 27 and 28: Introduction 1.3.11 Boronic ester e
Page 29: Introduction References 1. E. Mouli
Page 33 and 34: Introduction Figure 2.2 shows compu
Page 35 and 36: Introduction incorporate β-cyclode
Page 37 and 38: Introduction Trianglamine-Zn(R) 2 c
Page 39 and 40: Introduction 24. J. Gajewy, J. Gawr
Page 41 and 42: Scope of Work Scope of Work In this
Page 43 and 44: Scope of Work can be obtained from
Page 45 and 46: Scope of Work Figure 3.4 Structures
Page 47 and 48: Scope of Work References 1. G. Wrig
Page 49 and 50: Organic & Biomolecular Chemistry Ci
Page 51 and 52: Downloaded by Jacobs University Bre
Page 53 and 54: View Online Downloaded by Jacobs Un
Page 63 and 64: Paper 2 Rapid Commun. Mass Spectrom
Page 65 and 66: Trianglimine formation mechanism by
Page 75 and 76: Paper 3 Org. Biomol. Chem., 2012, 1
Page 81 and 82:
View Online Table 2 Distances (Å)
Page 83 and 84:
View Online Downloaded by Jacobs Un
Page 85 and 86:
Paper 4 Chem. Eur. J., 2012, submit
Page 87 and 88:
(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.
Page 95 and 96:
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 141 and 142:
Page 143 and 144:
Page 145 and 146:
Page 147 and 148:
Page 149 and 150:
Page 151 and 152:
Page 153 and 154:
Monitoring the [3+3]-cyclocondensat
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Monitoring the cyclocondensation re
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Product ions appeared as [M+H] + Fi
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Scheme 1. Assigned higher oligomers
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Supplementary Information: Synthesi
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Scheme 4. Proposed fragmentation me
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DMSO Figure 1. 1 H-NMR spectrum for
Page 167 and 168:
Figure 6. 13 C-NMR spectrum for (4S
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Intens. 7 x10 1.5 200.7 1.0 0.5 0.0
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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
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HN N O O R R NH O O N N HN R O O O
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Intens. 5 x10 727.2 2.0 1.5 1.0 O O
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Intens. 5 x10 697.1 1.5 1.0 728.2 0
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O O O O HN N O O NH N HN N O O NH N
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Figure 38. 1 H-NMR spectrum for mac
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Intens. 5000 276.8 4000 3000 2000 1
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Intens. 7 x10 599.1 1.5 1.0 0.5 0.0
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(a) HN N O O NH O O N (b) HN N O NH
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Scheme 11. Proposed fragmentation m
Page 193 and 194:
Page 195 and 196:
Scheme 14. Proposed fragmentation m
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Intens. 4 x10 550.9 3 2 1 0 500 100
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Figure 68. 2D-ROESY spectrum for ma
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Supplementary Information: Novel sy
Page 203 and 204:
Intens. 6 x10 0.8 0.6 0.4 240.9 459
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Figure 9. 1 H-NMR spectrum for macr
Page 207 and 208:
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 215 and 216:
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
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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
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
Page 247 and 248:
Intens. [%] 100 80 60 40 Free guest
Page 249 and 250:
Intens. 4 x10 1085.3575 1.25 1.00 0
Page 251 and 252:
Intens. [%] 100 80 Free guest 586.1
Page 253 and 254:
Synthesis, self-assembly and ESI-MS
Page 255 and 256:
O O HN NH HN O O NH HN O 11 O NH O
Page 257 and 258:
O O HN NH HN O O NH HN O 9 O NH O O
Page 259 and 260:
H 2 O DMSO DMSO Figure 6. 1 H-NMR a
Page 261 and 262:
Intens. 5 x10 5 -MS 487.1588 4 3 2
Page 263 and 264:
Intens. -MS 6 x10 0.8 0.6 0.4 0.2 1
Page 265 and 266:
Intens. -MS 6 x10 O O 350.9 1.5 1.0
Page 267 and 268:
Intens. [%] 100 -MS 486.9 Exact str
Page 269 and 270:
Intens. [%] -MS 100 486.9 80 60 975
Page 271 and 272:
Intens. [%] +MS 100 80 517.2 Exact
Page 273 and 274:
Intens. [%] 100 80 60 +MS 388.1 775
Page 275 and 276:
Intens. [%] 100 +MS 517.2 Exact str
Page 277 and 278:
Intens. [%] 100 80 +MS 1031.4939 7
Page 279 and 280:
Intens. [%] 100 +MS 517.2 Exact str
Page 281 and 282:
Intens. [%] 100 -MS 2 586.1 80 60 4
Page 283 and 284:
Intens. [%] 100 -MS 2 875.2 Exact s
Page 285 and 286:
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
Page 291:
4. H. Nour, A. López-Periago, N. K
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