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

More documents

Recommendations

Info

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
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 and 30:
Introduction References 1. E. Mouli
Page 31 and 32:
Introduction 51. B. Shi, M. F. Grea
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 55 and 56:
Page 57 and 58:
Page 59 and 60:
Page 61 and 62:
Page 63 and 64:
Paper 2 Rapid Commun. Mass Spectrom
Page 65 and 66:
Trianglimine formation mechanism by
Page 67 and 68:
Page 69 and 70:
Page 71 and 72:
Page 73 and 74:
Page 75 and 76:
Paper 3 Org. Biomol. Chem., 2012, 1
Page 77 and 78:
Page 79 and 80:
Page 81 and 82:
View Online Table 2 Distances (Å)
Page 83 and 84:
Page 85 and 86:
Paper 4 Chem. Eur. J., 2012, submit
Page 87 and 88:
(4R,5R)- and (4S,5S)-dimethyl-2,2-d
Page 89 and 90:
that two distinct conformational is
Page 91 and 92:
the thimble was recharged with fres
Page 93 and 94:
Paper 5 Rapid Commu. Mass Spectrom.
Page 95 and 96:
INTRODUCTION No single class of dru
Page 97 and 98:
EXPERIMENTAL All the solvents and r
Page 99 and 100:
(b) Refluxing macrocycles 5, 6 and
Page 101 and 102:
Scheme 1. Graphical representation
Page 103 and 104:
Figure 1. A plot of relative intens
Page 105 and 106:
In contrast, formation of library m
Page 107 and 108:
Figure 5. Generated dynamic library
Page 109 and 110:
macrocycle 32 from the dynamic libr
Page 111 and 112:
The polar carbamate group participa
Page 113 and 114:
[2] WHO World health report 2003. h
Page 115 and 116:
[32] B. Lienard, N. Selevsek, N. Ol
Page 117 and 118:
FULL PAPER Synthesis and ESI-MS Com
Page 119 and 120:
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 139 and 140:
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
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 193 and 194:
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 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
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
Page 287 and 288: 274 | P a g e
Page 289 and 290: 276 | P a g e
Page 291: 4. H. Nour, A. López-Periago, N. K
show all

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

You also want an ePaper? Increase the reach of your titles

Delete template?

Save as template?