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Intens. [%] 100 +MS 1450.6 Exact arrangements of host and guest molecules could not be assigned by MS /MS 80 1416.7 60 40 1484.6 20 1390.6 1424.6 1404.7 1438.6 1507.7 1517.6 0 1380 1400 1420 1440 1460 1480 1500 1520 m/z Figure 75. ESI-TOF/MS for higher Mwt complexes of receptor (7, 9 and 10) with 20. Figure 76. Proposed energy-minimized structure for two self-assembled molecules of receptor 7 recognizing D-(–)-quinic acid 14. Structure was optimized at the MM+ level using HyperChem software (Release 8.0). Both hydrogen bonding and π-π stacking interactions participate in stabilizing the hostguest complexes. 32 | S
Table 1. High resolution ESI-TOF/MS data for selective recognition of receptors 7, 9 and 10 to oligopeptide guests 19 and 20 Host/Guest Molecular Formula a Product Ions Calcd. m/z Meas. m/z Error [ppm] (7 and 9)/19 C 44 H 64 N 12 O 19 [(M 9 + M 19 ) + H] + 1065.4483 1065.4499 –1.5 C 42 H 60 N 12 O 17 [(M 7 + M 19 ) + H] + 1005.4272 1005.4309 –3.7 C 65 H 88 N 18 O 27 [(M 7 + M 9 + M 19 ) + H] + 1553.6139 1553.6148 –0.6 C 67 H 92 N 18 O 29 [(2M 9 + M 19 ) + H] + 1613.6350 1613.6363 –0.8 (7 and 9)/20 C 28 H 58 N 10 O 15 [(2M 20 ) + H] + 775.4156 775.4182 –3.3 C 39 H 57 N 11 O 16 [(M 9 + M 20 ) + H] + 936.4058 936.4081 –2.5 C 37 H 53 N 11 O 14 [(M 7 + M 20 ) + H] + 876.3846 876.3880 –3.9 C 58 H 77 N 17 O 22 [(2M 7 + M 20 ) + H] + 1364.5502 1364.5466 2.6 C 62 H 85 N 17 O 26 [(2M 9 + M 20 ) + H] + 1484.5924 1484.5889 2.4 C 60 H 81 N 17 O 24 [(M 7 + M 9 + M 20 ) + H] + 1424.5682 1424.5713 2.2 (7 and 10)/19 C 44 H 66 N 14 O 15 [(M 10 + M 19 ) + H] + 1031.4905 1031.4939 –3.3 (7 and 10)/20 C 39 H 59 N 13 O 12 [(M 10 + M 20 ) + H] + 902.4479 902.4445 3.8 C 37 H 53 N 11 O 14 [(M 7 + M 20 ) + H] + 876.3846 876.3800 5.3 C 32 H 58 N 10 O 12 [(2M 20 ) + H] + 775.4308 775.4305 0.5 (7, 9 and 10)/19 C 44 H 66 N 14 O 15 [(M 10 + M 19 ) + H] + 1031.4905 1031.4897 0.8 C 44 H 64 N 12 O 19 [(M 9 + M 19 ) + H] + 1065.4483 1065.4462 2.0 C 46 H 60 N 16 O 12 [(2M 10 ) + H] + 1029.4649 1029.4696 –4.5 C 46 H 58 N 14 O 16 [(M 9 + M 10 ) + H] + 1063.4228 1063.4250 –2.1 (7, 9 and 10)/20 C 39 H 57 N 11 O 16 [(M 9 + M 20 ) + H] + 936.4058 936.4069 –1.2 C 39 H 59 N 13 O 12 [(M 10 + M 20 ) + H] + 902.4479 902.4520 –4.5 C 37 H 53 N 11 O 14 [(M 7 + M 20 ) + H] + 876.3846 876.3889 –4.9 C 62 H 88 N 19 O 22 [(M 9 + M 10 + M 20 ) + H] + 1450.6346 1450.6369 –1.6 C 62 H 89 N 21 O 18 [(2M 10 + M 20 ) + H] + 1416.6767 1416.6775 –0.6 C 62 H 85 N 17 O 26 [(2M 9 + M 20 ) + H] + 1484.5924 1484.5928 –0.2 a ESI-TOF/MS recorded in the positive ion mode. 33 | S
Page 1 and 2:
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
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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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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: Intens. [%] 100 -MS 2 875.2 Exact s
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Page 291: 4. H. Nour, A. López-Periago, N. K
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