Nucleophilic active site mimetics and methodological advances in activity-based protein profiling:
Gespeichert in:
| 1. Verfasser: | |
|---|---|
| Format: | Abschlussarbeit Buch |
| Sprache: | English |
| Veröffentlicht: |
München
Verl. Dr. Hut
2014
|
| Ausgabe: | 1. Aufl. |
| Schriftenreihe: | Organische Chemie
|
| Schlagworte: | |
| Online-Zugang: | Inhaltsverzeichnis |
| Beschreibung: | XV, 193 S. Ill., graph. Darst. |
| ISBN: | 9783843914475 |
Internformat
MARC
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| 245 | 1 | 0 | |a Nucleophilic active site mimetics and methodological advances in activity-based protein profiling |c Georg Christoph Rudolf |
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| 264 | 1 | |a München |b Verl. Dr. Hut |c 2014 | |
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Datensatz im Suchindex
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| adam_text | I
I TABLE OF CONTENTS
1 TABLE OF CONTENTS I
2 INTRODUCTORY REMARKS III
3 SUMMARY V
4 ZUSAMMENFASSUNG IX
5 LIST OF ABBREVIATIONS, ACRONYMS AND SYMBOLS XIV
1 INTRODUCTION L
1.1 ACTIVITY-BASED PROTEIN PROFILING L
I
.
I
.
I
BASIC PROCEDURES OF ABPP EXPERIMENTS 3
1.2 SCOPE OF THIS WORK 4
2 TRIFUNCTIONAL LINKER 2
ND
GENERATION 7
2.1 INTRODUCTION 7
2.2 TRIFUNCTIONAL LINKERS: CATCHING, REPORTING & ENRICHMENT 8
2.3 RATIONAL DESIGN OF TRIFUNCTIONAL LINKER 2
ND
GENERATION 9
2.4 SYNTHESIS OF TRIFUNCTIONAL LINKER 2
ND
GENERATION 10
2.5 EVALUATION OFTFL-2
D
IN THE ABPP PROCESS IT
3 CLEAVABLE LINKERS FOR IMMOBILIZATION AND ENRICHMENT 13
3.1 INTRODUCTION 13
3.2 CURRENT CLEAVAGE METHODS FOR PROTEIN MODIFICATIONS 14
3.2.1 CLEAVAGE OF THERMAL- AND PHOTOCLEAVABLE LINKERS 14
3.2.2 CLEAVAGE BY CHEMICAL REAGENTS: ACID- AND REDUCTION-BASED METHODS
15
3.3 RESULTS AND DISCUSSION 17
3.3.1 NOVEL APPROACH FOR BASE-CLEAVABLE LINKERS 17
3.3.2 SYNTHESES OF MODEL COMPOUNDS FOR PRELIMINARY EVALUATIONS 18
3.3.3 PRELIMINARY EVALUATION OF MODEL LINKERS 21
3.3.4 SYNTHESES OF PROTOTYPICAL LINKERS FOR ENRICHMENT PURPOSES 25
3.4 CONCLUDING REMARKS 27
4 ENHANCEMENT OF COPPER-ASSISTED CLICK REACTIONS FOR ACTIVITY-BASED
PROTEOMICS 29
4.1 INTRODUCTION 29
4.2 RESULTS AND DISCUSSION 31
4.2.1 RATIONAL DESIGN AND SYNTHESES OF TAILORED LIGANDS 31
4.2.2 KINETIC ANALYSES AND OPTIMIZATION OF REACTION CONDITIONS 33
4.2.3 EVALUATION OF BIOORTHOGONAL CLICK REACTIONS FOR IN VITRO ABPP
LABELLING 35
4.3 CONCLUDING REMARKS 40
5 NUCLEOPHILIC ACTIVE SITE MIMETICS 43
5.1 INTRODUCTION 43
5.2 DISCOVERY OF ELECTROPHILIC NATURAL PRODUCTS 44
5.2.1 ELECTROPHILIC NATURAL PRODUCTS 44
5.2.2 METHODS FOR THE IDENTIFICATION OF NATURAL PRODUCTS 45
HTTP://D-NB.INFO/1048241602
II
5.3 NUCLEOPHILIC ACTIVE SITE MIMETICS APPROACH 46
5.3.1 PRIVILEGED STRUCTURES FOR NASM PROBES 47
5.3.2 PROJECT OUTLINE FOR PROOF-OF-CONCEPT STUDY 48
5.4 RESULTS AND DISCUSSION 49
5.4.1 SYNTHESES OF NASM PROBES 49
5.4.2 EVALUATION OF NASM PROBES REACTIVITY UNDER BIOORTHOGONAL
CONDITIONS 54
5.4.3 EVALUATION WITH MODEL SYSTEM SHOWDOMYCIN 60
5.5 CONCLUDING REMARKS AND OUTLOOK 64
6 EXPERIMENTAL SECTION 67
6.1 SYNTHETIC ORGANIC CHEMISTRY 67
6.1.1 GENERAL METHODS AND MATERIALS 67
6.1.2 SYNTHETIC PROCEDURES FOR CHAPTER 2: TRIFUNCTIONAL LINKER 2
ND
GENERATION 69
6.1.3 SYNTHETIC PROCEDURES FOR CHAPTER 3: CLEAVABLE LINKERS FOR
IMMOBILIZATION AND
ENRICHMENT 71
6.1.4 SYNTHETIC PROCEDURES FOR CHAPTER 4: ENHANCEMENT OF COPPER-ASSISTED
CLICK
REACTIONS FOR ACTIVITY-BASED PROTEOMICS 85
6.1.5 SYNTHETIC PROCEDURES FOR CHAPTER 5: NUCLEOPHILIC ACTIVE SITE
MIMETICS 100
6.1.6 SYNTHETIC PROCEDURES FOR STUDIES TOWARDS THE IDENTIFICATION OF
ASP-PHOS
MODIFICATIONS 116
6.2 BIOCHEMISTRY AND RELATED PROCEDURES 121
6.2.1 GENERAL METHODS AND MATERIALS 121
6.2.2 FLUORESCENCE-BASED KINETIC EXPERIMENTS OF CHAPTER 4 124
6.2.3 PROTEOMICS: PROCEDURES FOR ANALYTICAL IN VITRO LABELLING
EXPERIMENTS OF CHAPTER
4 125
6.2.4 PROTEOMICS: PROCEDURES FOR PREPARATIVE LABELLING AND
IDENTIFICATION EXPERIMENTS
OF CHAPTER 4 127
6.2.5 REACTIVITY EVALUATION EXPERIMENTS OF CHAPTER 5 129
7 BIBLIOGRAPHY 131
8 CURRICULUM VITAE AND ACKNOWLEDGEMENTS 147
9 APPENDICES 151
9.1 APPENDIX FOR CHAPTER 4: ENHANCEMENT OF COPPER-ASSISTED CLICK
REACTIONS FOR
ACTIVITY-BASED PROTEOMICS 151
9.1.1 SELECTED H AND
13
C NMR SPECTRA 152
9.1.2 KINETIC ANALYSES AND OPTIMIZATION OF REACTION CONDITIONS 170
9.1.3 IN VITRO LABELLING EXPERIMENTS WITH B. SUBTILIS PROTEOME 175
9.2 APPENDIX FOR CHAPTER 5: NUCLEOPHILIC ACTIVE SITE MIMETICS 181
9.2.1 SELECTED H AND
13
C NMR SPECTRA 182
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| isbn | 9783843914475 |
| language | English |
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| series2 | Organische Chemie |
| spelling | Rudolf, Georg C. Verfasser aut Nucleophilic active site mimetics and methodological advances in activity-based protein profiling Georg Christoph Rudolf 1. Aufl. München Verl. Dr. Hut 2014 XV, 193 S. Ill., graph. Darst. txt rdacontent n rdamedia nc rdacarrier Organische Chemie Zugl.: München, Techn. Univ., Diss., 2014 Markierung Chemie (DE-588)4201779-8 gnd rswk-swf Struktur-Aktivitäts-Beziehung (DE-588)4183784-8 gnd rswk-swf Proteomanalyse (DE-588)4596545-6 gnd rswk-swf (DE-588)4113937-9 Hochschulschrift gnd-content Proteomanalyse (DE-588)4596545-6 s Struktur-Aktivitäts-Beziehung (DE-588)4183784-8 s Markierung Chemie (DE-588)4201779-8 s DE-604 DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=027169480&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Rudolf, Georg C. Nucleophilic active site mimetics and methodological advances in activity-based protein profiling Markierung Chemie (DE-588)4201779-8 gnd Struktur-Aktivitäts-Beziehung (DE-588)4183784-8 gnd Proteomanalyse (DE-588)4596545-6 gnd |
| subject_GND | (DE-588)4201779-8 (DE-588)4183784-8 (DE-588)4596545-6 (DE-588)4113937-9 |
| title | Nucleophilic active site mimetics and methodological advances in activity-based protein profiling |
| title_auth | Nucleophilic active site mimetics and methodological advances in activity-based protein profiling |
| title_exact_search | Nucleophilic active site mimetics and methodological advances in activity-based protein profiling |
| title_full | Nucleophilic active site mimetics and methodological advances in activity-based protein profiling Georg Christoph Rudolf |
| title_fullStr | Nucleophilic active site mimetics and methodological advances in activity-based protein profiling Georg Christoph Rudolf |
| title_full_unstemmed | Nucleophilic active site mimetics and methodological advances in activity-based protein profiling Georg Christoph Rudolf |
| title_short | Nucleophilic active site mimetics and methodological advances in activity-based protein profiling |
| title_sort | nucleophilic active site mimetics and methodological advances in activity based protein profiling |
| topic | Markierung Chemie (DE-588)4201779-8 gnd Struktur-Aktivitäts-Beziehung (DE-588)4183784-8 gnd Proteomanalyse (DE-588)4596545-6 gnd |
| topic_facet | Markierung Chemie Struktur-Aktivitäts-Beziehung Proteomanalyse Hochschulschrift |
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