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

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Intens. 2000 The peak intensity for host/guest B/15 complex is ~ 2000 1246.3865 –MS 1500 1247.3435 1000 500 0 1248.3218 1241.7864 1242.7830 1243.7846 1246.7690 1247.8125 1242 1243 1244 1245 1246 1247 1248 m/z Intens. 5 x10 1.25 +MS 796.2573 The peak intensity for host/guest 7/15 complex is ~ 10 5 1.00 0.75 0.50 0.25 1284.4226 0.00 500 1000 1500 2000 2500 3000 3500 4000 4500 m/z Figure 46. Comparison between ESI-TOF/MS for (receptor/guest, 7/15) and (macrocycle/guest, B/15). Intens. [%] 100 +MS 1065.4499 7 = 9 = 19 = 80 60 40 20 1005.4309 1033.5077 0 1000 1010 1020 1030 1040 1050 1060 1070 1080 m/z Figure 47. ESI-TOF/MS showing selective recognition of oligopeptide 19 by receptor 9. 22 | S
Intens. [%] 100 +MS 517.2 Exact structure 80 19 60 1065.4 40 20 0 500 1000 1500 2000 2500 m/z Figure 48. Tandem ESI-MS for host-guest complex (7 and 9)/19 (MS 2 for m/z 1065). Intens. [%] 100 +MS 517.2 1005.3 Exact structure 80 60 40 20 0 500 1000 1500 2000 2500 m/z Figure 49. Tandem ESI-MS for host-guest complex (7 and 9)/19 (MS 2 for m/z 1005). Intens. [%] 100 80 7 = 9 = 20 = 876.3880 9 +MS 936.4081 20 60 40 775.4182 20 924.4069 0 780 800 820 840 860 880 900 920 940 m/z Figure 50. ESI-TOF/MS showing recognition of oligopeptide 20 by receptors 7 and 9. 23 | S
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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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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
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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
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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
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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
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Intens. 6 x10 0.8 0.6 0.4 240.9 459
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Figure 9. 1 H-NMR spectrum for macr
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Intens. 5 x10 1.5 968.1 1.0 0.5 813
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Intens. 5 x10 897.4 4 2 335.3 707.3
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Scheme 3. Suggested fragmentation m
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Molecular modelling data for the co
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Figure 1. 1 H NMR spectrum for dica
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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
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: Intens. [%] 100 80 60 +MS 388.1 775
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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Page 291: 4. H. Nour, A. López-Periago, N. K
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