Cis-trans isomerization in biochemistry:
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| Format: | Buch |
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| Sprache: | English |
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Weinheim
Wiley-VCH-Verl.
2006
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| Beschreibung: | Literaturangaben |
| Beschreibung: | XV, 354 S. Ill., graph. Darst. 25 cm |
| ISBN: | 9783527313044 3527313044 |
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| 245 | 1 | 0 | |a Cis-trans isomerization in biochemistry |c ed. by Christophe Dugave |
| 264 | 1 | |a Weinheim |b Wiley-VCH-Verl. |c 2006 | |
| 300 | |a XV, 354 S. |b Ill., graph. Darst. |c 25 cm | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 500 | |a Literaturangaben | ||
| 650 | 7 | |a Bioquímica |2 larpcal | |
| 650 | 4 | |a Cis-trans isomérases | |
| 650 | 4 | |a Isomérisation | |
| 650 | 4 | |a Liaisons doubles (Chimie) | |
| 650 | 4 | |a Peptidylprolyl isomerase | |
| 650 | 4 | |a Biochemistry | |
| 650 | 4 | |a Biomolecules | |
| 650 | 4 | |a Isomerism | |
| 650 | 4 | |a Stereochemistry | |
| 650 | 0 | 7 | |a Biomolekül |0 (DE-588)4135124-1 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a cis-trans-Isomerie |0 (DE-588)4148046-6 |2 gnd |9 rswk-swf |
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| 689 | 0 | 1 | |a cis-trans-Isomerie |0 (DE-588)4148046-6 |D s |
| 689 | 0 | |5 DE-604 | |
| 700 | 1 | |a Dugave, Christophe |e Sonstige |4 oth | |
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Datensatz im Suchindex
| _version_ | 1804135702943760384 |
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| adam_text | I«
Contents
Preface XI
List of Contributors XIII
1 Nomenclature 1
Christophe Dugave
2 General Mechanisms of G s-Trans Isomerization: A Rapid Survey 7
Christophe Dugave
2.1 Introduction 7
2.2 Homolytic Cis-Trans Isomerization 7
2.3 Heterolytic Cis-Trans Isomerization 10
3 Mechanisms of Cis-Trans Isomerization around the Carbon-Carbon Double
Bonds via the Triplet State 15
Yasushi Koyama, Yoshinori Kakitani, and Hiroyoshi Nagae
3.1 A Conceptofa Triplet-Excited Region 25
3.2 Triplet-State Isomerization in Retinal 17
3.2.1 Cis-Trans Isomerization Examined by Electronic Absorption
and Raman Spectroscopies and by High-Performance Liquid
Chromatography Analysis 17
3.2.2 Triplet-Excited Region in All-trans-Retinal Shown in Terms of
Stretching Force Constants Determined by Raman Spectroscopy and
Normal Coordinate Analysis 22
3.2.3 Dynamic Triplet-Excited Region in Retinal As Revealed by Deuteration
Effects on the Quantum Yields of Isomerization via the Tx State 24
3.2.4 Summary and Future Trends 26
3.3 Triplet-State Isomerization in /S-Carotene and Spheroidene 27
3.3.1 Cis-Trans Isomerization in ß-Carotene Studied by Electronic
Absorption and Raman Spectroscopies and by HPLC Analysis 27
cis-trans Isomerization in Biochemistry. Edited by Christophe Dugave
Copyright © 2006 WILEY-VCH Verlag GmbH Co. KGaA, Weinheim
ISBN: 3-527-31304-4
VI I Contents
3.3.2 Cis-Trans Isomerization in Spheroidene Studied by Time-Resolved
Absorption Spectroscopy and by HPLC Analysis 32
3.3.3 The Triplet-Excited Region of All-trons-Spheroidene in Solution and
the Triplet-State Structure of 15-cis-Spheroidene Bound to the Bacterial
Reaction Center Determined by Raman Spectroscopy and Normal
Coordinate Analysis 35
3.3.3.1 All-traws-Spheroidene in Solution 35
3.3.3.2 15-cis-Spheroidene Bound to the Reaction Center 37
3.3.4 Conformational Changes and the Inversion of Spin-Polarization
Identified by Low-Temperature Electron Paramagnetic Resonance
Spectroscopy of the Reaction Center-Bound 15-cis-Spheroidene: A
Hypothetical Mechanism of Triplet-Energy Dissipation 39
3.3.5 Summary and Future Trends 46
3.4 Spectroscopic and Analytical Techniques for Studying Cis-Trans
Isomerization in the Tj State 47
3.4.1 Spectroscopic Techniques: Electronic Absorption, Raman, and
Magnetic Resonance Spectroscopies 47
3.4.2 A Useful Analytical Technique: Singular-Value Decomposition
Followed by Global Firting 48
4 Retinal Binding Proteins 53
Hideki Kandori
4.1 Retinal Chromophore in Rhodopsins 53
4.1.1 Specific Color Regulation of the Retinal Chromophore in Protein 53
4.1.2 Unique Photochemistry of the Retinal Chromophore in Protein 56
4.2 Photoisomerization in Visual Rhodopsins 57
4.2.1 Structure and Function of Visual Rhodopsins 57
4.2.2 Primary Process in Vision Studied by Ultrafast Spectroscopy 59
4.2.3 Structural Changes of the Chromophore and Protein upon
Retinal Photoisomerization 64
4.3 Photoisomerization in Archaeal Rhodopsins 66
4.3.1 Structure and Function of Archaeal Rhodopsin 66
4.3.2 Primary Process in Bacterial Photosynthesis and Light Sensor Studied
by Ultrafast Spectroscopy 68
4.3.3 Structural Changes of the Chromophore and Protein upon
Retinal Photoisomerization 69
4.4 Summary and Prospects 72
5 Non-Retinal Chromophoric Proteins 77
Marc Zimmer
5.1 Introduction 77
5.2 Photoactive Yellow Protein 77
5.3 Green Fluorescent Protein and Other GFP-like Proteins 79
5.4 Phytochromes 89
Contents I VII
6 Fatty Acids and Phospholipids 95
Chryssostomos Chatgilialoglu and Carla Ferreri
6.1 Introduction 95
6.2 Enzyme-Catalyzed Cis-Trans Isomerization of Unsaturated Fatty Acid
Residues in Bacteria 97
6.3 Radical-Catalyzed Cis-Trans Isomerization of Unsaturated Lipids and
its Effect on Biological Membranes 101
6.3.1 Geometrie Isomerization of Unsaturated Fatty Acids in Solution 101
6.3.2 Isomerization of Phosphatidylcholine in Large Unilamellar
Vesicles 103
6.3.3 Biological Consequences 106
6.4 Perspectives and Future Research 110
7 In Silico Dynamic Studies of Cis-Trans Isomerization in Organic
and Biological Systems 113
Ute F. Röhrig, Wano Tavernelli, and Ursula Rothlisberger
7.1 Introduction 323
7.2 Computational Methods 116
7.2.1 Time-Dependent Density Functional Theory (TDDFT) 116
7.2.2 Restricted Open-Shell Kohn-Sham Theory (ROKS) 120
7.3 TheoreticalAspectsofCTI 122
7.3.1 Protonated Schiff Bases 123
7.3.2 Formaldimine 124
7.4 CTI in PSB5 and Formaldimine 124
7.4.1 Protonated Schiff Base (PSB5) 124
7.4.2 Formaldimine 129
7.5 CTI in Rhodopsin 132
7.5.1 Introduction 132
7.5.2 Classical and QM/MM Studies of the CTI in Rhodopsin 133
7.6 Summary and Condusions 137
8 Chemical Aspects ofthe Restricted Rotation of Esters, Amides,
and Related Compounds 143
Christophe Dugave
8.1 Thermodynamic and Kinetic Aspects of Cis-Trans Isomerization 143
8.1.1 Esters and Thioesters 144
8.1.2 Amides and Thioxoamides 145
8.1.3 Oxalamides and Hydrazides 147
8.1.4 Carbamates and Ureas 148
8.2 Influence ofthe Environment on CTI 150
8.2.1 Solvent and Concentration HO
8.2.2 pH and Salts 252
8.2.3 Temperature 253
VIII I Contents
8.3 The Study of CTI of Amides and other Conjugated Jt-Systems 154
8.3.1 Spectroscopic Techniques 354
8.3.1.1 NMR Spectroscopy 154
8.3.1.2 Spectrometric and Fluorimetric Assays 355
8.3.1.3 Other Spectroscopic Techniques 157
8.3.2 Separation ofZ and FIsomers 158
8.3.3 Models and Mimics for the Study of Amide CTI: Towards Multiple
CTI Pathways 159
8.3.3.1 Acid/H-Bond-Catalyzed CTI 360
8.3.3.2 Nucleophilic/BasicCatalysisofCTI 161
8.3.3.3 Cation-Catalyzed CTI 363
8.3.3.4 Light-Induced CTI 363
9 Amide Cis-Trans Isomerization in Peptides and Proteins 367
Stephan Wawra and Gunter Fischer
9.1 Imidic and Secondary Amide Peptide Bond Conformation 367
9.1.1 Simple Amides 367
9.1.2 Secondary Amide Peptide Bonds 169
9.1.3 Imidic Peptide Bonds 171
9.1.4 Solvent and pH Effects 173
9.1.5 Sequence-Specific Effects 174
9.1.6 Secondary Structure Formation and CTI 178
9.2 Amide Relevant Conformations in Proteins 181
9.3 Native State Peptide Bond Isomerization 383
9.4 Biological Consequences 187
10 Enzymes Catalyzing Peptide Bond Cis-Trans Isomerizations 195
Gunter Fischer
10.1 Introduction 195
10.2 Cydophilins 199
10.3 FK506 Binding Proteins (FKBPs) 204
10.4 Trigger Factor 209
10.5 Parvulins 210
10.6 Secondary Amide Peptide Bond Cis-Trans Isomerases 213
10.7 Catalytic Mechanism of Peptide Bond Cis-Trans Isomerases 235
11 Tailoring the Cis-Trans Isomerization of Amides 225
Luis Moroder and Christian Renner
JohnJ. Lopez, Gabriele Tuchscherer and Manfred Mutter
11.1 Introduction 225
11.2 Substituted Prolines 225
11.2.1 Hydroxyprolines 226
11.2.2 Mercaptoproline 229
Contents I IX
11.2.3 Halogenated Prolines 230
11.2.4 Other Proline Analogs 232
11.2.5 Alkylated Proline Analogs 233
11.2.6 Bridged Bicyclic Proline Analogs 235
11.2.7 Locked Proline Mimetics 237
11.3 Pseudoprolines in Chemical Synthesis and Biology 240
11.3.1 From Proline to Pseudoproline 240
11.3.2 Synthesis of Pseudoprolines 242
11.3.3 Pseudoprolines for the Synthesis of Difficult Sequences 244
11.3.4 Pseudoprolines in Bioactive Peptides 245
11.3.5 Pseudoprolines for Enhancing Peptide Cyclization and Turn
Induction 246
11.3.6 Pseudoprolines for Modulating Polyproline Heikes 247
11.3.7 Pseudoprolines for Modulating Structure and Function of
Cyclosporins 249
11.3.8 Pseudoprolines for Targeting Cis Bonds in Peptides
and Proteins 251
11.4 Conclusions and Perspectives 252
12 Peptidyl Prolyl Isomerases: New Targets for Novel Therapeutics? 261
Christophe Dugave
12.1 Introduction 262
12.2 Implication of PPIases in Biological Processes and Diseases 262
12.2.1 PPIases and Protein Folding and Trafficking 262
12.2.2 Immunosuppressive Pathways Through Formation of
PPIase:Ligand Complexes 263
12.2.3 Modulation of Ion Channels by PPIases 265
12.2.4 Chaperone Activity of Immunophilins in Steroid Receptor
Signaling 265
12.2.5 Immunophilins and Neurodegenerative Disorders 266
12.2.6 PPIases and Cell Multiplication 267
12.2.7 Implication of PPIases in Apoptosis 270
12.2.8 PPIases and Infectious Diseases 270
12.3 Structure and SAR studies of PPIases: Structural Evidence and
Putative Catalytic Mechanism 272
12.3.1 Generalities 272
12.3.2 Cyclophilins and FKBPs: Similar Molecular Basis for
Distinct Catalytic Mechanisms 273
12.3.3 Parvulins 276
12.4 PPIase Inhibitors: From In Vitro Inhibitors to Novel
Therapeutics 277
12.4.1 Natural PPIase Inhibitors and Their Analogs 277
12.4.2 Mechanism-Based Inhibitors 282
X I Contents
12.4.3 Library Screening Versus in Silico Design: Current Status
and Future Prospects 284
12.5 Conclusion and Perspectives 288
13 Other Cis-Trans Isomerizations in Organic Molecules
and Biomolecules 295
Muriel Gondry and Christophe Dugave
13.1 Introduction 295
13.2 Cis-Trans Isomerization around Single Bonds 295
13.2.1 Cis-Trans Isomerism ofAryl Compounds 295
13.2.2 Disulfide Bonds 297
13.2.3 Amide Surrogates with Restricted Rotation of a oBond 298
13.3 C=N-containing Compounds 300
13.3.1 Oximes and Nitroso Compounds 300
13.3.2 Imines and Schiff Bases 300
13.4 Dehydroamino Acids and Dehydropeptides 303
13.4.1 Acryloyl Peptides, Acrylates and Related Molecules 303
13.4.2 Naturally Occurring Dehydroamino Acids and Dehydropeptides 305
13.4.3 Synthetic Dehydroamino Acids and Dehydropeptides 308
13.5 Phototunable Biomolecules Containing an Azobenzene Moiety 320
13.5.1 Phototunable Ligands 310
13.5.2 Phototunable Conformation of Peptides 312
13.5.3 Modifkations of Proteins with Photoisomerizable Motifs 313
13.5.4 Other Phototunable Biomolecules 315
14 Cis-Trans Isomerism in Metal Complexes 321
Alzir Azevedo Batista and Salete Linhares Queiroz
14.1 Introduction 321
14.1.1 Trans Effect 324
14.1.2 Protonation ofthe Leaving Group 326
14.1.3 Separation or Purification of Cis-Trans Isomers 327
14.1.4 Identification of Cis-Trans Isomers 327
14.2 The Cis-Trans Isomerization of Metal Complexes: Mechanisms and
Effects 330
14.2.1 Cis or Trans Isomer? 330
14.2.2 Isomerization Processes 331
14.3 Cis-Trans Isomers of Metal Complexes as Potential Therapeutics 334
14.4 Applications of Cis-Trans Isomerization of Metal Complexes in
Supramolecular Chemistry 337
14.5 Final Remarks 341
Index 345
|
| adam_txt |
I«
Contents
Preface XI
List of Contributors XIII
1 Nomenclature 1
Christophe Dugave
2 General Mechanisms of G's-Trans Isomerization: A Rapid Survey 7
Christophe Dugave
2.1 Introduction 7
2.2 Homolytic Cis-Trans Isomerization 7
2.3 Heterolytic Cis-Trans Isomerization 10
3 Mechanisms of Cis-Trans Isomerization around the Carbon-Carbon Double
Bonds via the Triplet State 15
Yasushi Koyama, Yoshinori Kakitani, and Hiroyoshi Nagae
3.1 A Conceptofa Triplet-Excited Region 25
3.2 Triplet-State Isomerization in Retinal 17
3.2.1 Cis-Trans Isomerization Examined by Electronic Absorption
and Raman Spectroscopies and by High-Performance Liquid
Chromatography Analysis 17
3.2.2 Triplet-Excited Region in All-trans-Retinal Shown in Terms of
Stretching Force Constants Determined by Raman Spectroscopy and
Normal Coordinate Analysis 22
3.2.3 Dynamic Triplet-Excited Region in Retinal As Revealed by Deuteration
Effects on the Quantum Yields of Isomerization via the Tx State 24
3.2.4 Summary and Future Trends 26
3.3 Triplet-State Isomerization in /S-Carotene and Spheroidene 27
3.3.1 Cis-Trans Isomerization in ß-Carotene Studied by Electronic
Absorption and Raman Spectroscopies and by HPLC Analysis 27
cis-trans Isomerization in Biochemistry. Edited by Christophe Dugave
Copyright © 2006 WILEY-VCH Verlag GmbH Co. KGaA, Weinheim
ISBN: 3-527-31304-4
VI I Contents
3.3.2 Cis-Trans Isomerization in Spheroidene Studied by Time-Resolved
Absorption Spectroscopy and by HPLC Analysis 32
3.3.3 The Triplet-Excited Region of All-trons-Spheroidene in Solution and
the Triplet-State Structure of 15-cis-Spheroidene Bound to the Bacterial
Reaction Center Determined by Raman Spectroscopy and Normal
Coordinate Analysis 35
3.3.3.1 All-traws-Spheroidene in Solution 35
3.3.3.2 15-cis-Spheroidene Bound to the Reaction Center 37
3.3.4 Conformational Changes and the Inversion of Spin-Polarization
Identified by Low-Temperature Electron Paramagnetic Resonance
Spectroscopy of the Reaction Center-Bound 15-cis-Spheroidene: A
Hypothetical Mechanism of Triplet-Energy Dissipation 39
3.3.5 Summary and Future Trends 46
3.4 Spectroscopic and Analytical Techniques for Studying Cis-Trans
Isomerization in the Tj State 47
3.4.1 Spectroscopic Techniques: Electronic Absorption, Raman, and
Magnetic Resonance Spectroscopies 47
3.4.2 A Useful Analytical Technique: Singular-Value Decomposition
Followed by Global Firting 48
4 Retinal Binding Proteins 53
Hideki Kandori
4.1 Retinal Chromophore in Rhodopsins 53
4.1.1 Specific Color Regulation of the Retinal Chromophore in Protein 53
4.1.2 Unique Photochemistry of the Retinal Chromophore in Protein 56
4.2 Photoisomerization in Visual Rhodopsins 57
4.2.1 Structure and Function of Visual Rhodopsins 57
4.2.2 Primary Process in Vision Studied by Ultrafast Spectroscopy 59
4.2.3 Structural Changes of the Chromophore and Protein upon
Retinal Photoisomerization 64
4.3 Photoisomerization in Archaeal Rhodopsins 66
4.3.1 Structure and Function of Archaeal Rhodopsin 66
4.3.2 Primary Process in Bacterial Photosynthesis and Light Sensor Studied
by Ultrafast Spectroscopy 68
4.3.3 Structural Changes of the Chromophore and Protein upon
Retinal Photoisomerization 69
4.4 Summary and Prospects 72
5 Non-Retinal Chromophoric Proteins 77
Marc Zimmer
5.1 Introduction 77
5.2 Photoactive Yellow Protein 77
5.3 Green Fluorescent Protein and Other GFP-like Proteins 79
5.4 Phytochromes 89
Contents I VII
6 Fatty Acids and Phospholipids 95
Chryssostomos Chatgilialoglu and Carla Ferreri
6.1 Introduction 95
6.2 Enzyme-Catalyzed Cis-Trans Isomerization of Unsaturated Fatty Acid
Residues in Bacteria 97
6.3 Radical-Catalyzed Cis-Trans Isomerization of Unsaturated Lipids and
its Effect on Biological Membranes 101
6.3.1 Geometrie Isomerization of Unsaturated Fatty Acids in Solution 101
6.3.2 Isomerization of Phosphatidylcholine in Large Unilamellar
Vesicles 103
6.3.3 Biological Consequences 106
6.4 Perspectives and Future Research 110
7 In Silico Dynamic Studies of Cis-Trans Isomerization in Organic
and Biological Systems 113
Ute F. Röhrig, Wano Tavernelli, and Ursula Rothlisberger
7.1 Introduction 323
7.2 Computational Methods 116
7.2.1 Time-Dependent Density Functional Theory (TDDFT) 116
7.2.2 Restricted Open-Shell Kohn-Sham Theory (ROKS) 120
7.3 TheoreticalAspectsofCTI 122
7.3.1 Protonated Schiff Bases 123
7.3.2 Formaldimine 124
7.4 CTI in PSB5 and Formaldimine 124
7.4.1 Protonated Schiff Base (PSB5) 124
7.4.2 Formaldimine 129
7.5 CTI in Rhodopsin 132
7.5.1 Introduction 132
7.5.2 Classical and QM/MM Studies of the CTI in Rhodopsin 133
7.6 Summary and Condusions 137
8 Chemical Aspects ofthe Restricted Rotation of Esters, Amides,
and Related Compounds 143
Christophe Dugave
8.1 Thermodynamic and Kinetic Aspects of Cis-Trans Isomerization 143
8.1.1 Esters and Thioesters 144
8.1.2 Amides and Thioxoamides 145
8.1.3 Oxalamides and Hydrazides 147
8.1.4 Carbamates and Ureas 148
8.2 Influence ofthe Environment on CTI 150
8.2.1 Solvent and Concentration HO
8.2.2 pH and Salts 252
8.2.3 Temperature 253
VIII I Contents
8.3 The Study of CTI of Amides and other Conjugated Jt-Systems 154
8.3.1 Spectroscopic Techniques 354
8.3.1.1 NMR Spectroscopy 154
8.3.1.2 Spectrometric and Fluorimetric Assays 355
8.3.1.3 Other Spectroscopic Techniques 157
8.3.2 Separation ofZ and FIsomers 158
8.3.3 Models and Mimics for the Study of Amide CTI: Towards Multiple
CTI Pathways 159
8.3.3.1 Acid/H-Bond-Catalyzed CTI 360
8.3.3.2 Nucleophilic/BasicCatalysisofCTI 161
8.3.3.3 Cation-Catalyzed CTI 363
8.3.3.4 Light-Induced CTI 363
9 Amide Cis-Trans Isomerization in Peptides and Proteins 367
Stephan Wawra and Gunter Fischer
9.1 Imidic and Secondary Amide Peptide Bond Conformation 367
9.1.1 Simple Amides 367
9.1.2 Secondary Amide Peptide Bonds 169
9.1.3 Imidic Peptide Bonds 171
9.1.4 Solvent and pH Effects 173
9.1.5 Sequence-Specific Effects 174
9.1.6 Secondary Structure Formation and CTI 178
9.2 Amide Relevant Conformations in Proteins 181
9.3 Native State Peptide Bond Isomerization 383
9.4 Biological Consequences 187
10 Enzymes Catalyzing Peptide Bond Cis-Trans Isomerizations 195
Gunter Fischer
10.1 Introduction 195
10.2 Cydophilins 199
10.3 FK506 Binding Proteins (FKBPs) 204
10.4 Trigger Factor 209
10.5 Parvulins 210
10.6 Secondary Amide Peptide Bond Cis-Trans Isomerases 213
10.7 Catalytic Mechanism of Peptide Bond Cis-Trans Isomerases 235
11 Tailoring the Cis-Trans Isomerization of Amides 225
Luis Moroder and Christian Renner
JohnJ. Lopez, Gabriele Tuchscherer and Manfred Mutter
11.1 Introduction 225
11.2 Substituted Prolines 225
11.2.1 Hydroxyprolines 226
11.2.2 Mercaptoproline 229
Contents I IX
11.2.3 Halogenated Prolines 230
11.2.4 Other Proline Analogs 232
11.2.5 Alkylated Proline Analogs 233
11.2.6 Bridged Bicyclic Proline Analogs 235
11.2.7 Locked Proline Mimetics 237
11.3 Pseudoprolines in Chemical Synthesis and Biology 240
11.3.1 From Proline to Pseudoproline 240
11.3.2 Synthesis of Pseudoprolines 242
11.3.3 Pseudoprolines for the Synthesis of Difficult Sequences 244
11.3.4 Pseudoprolines in Bioactive Peptides 245
11.3.5 Pseudoprolines for Enhancing Peptide Cyclization and Turn
Induction 246
11.3.6 Pseudoprolines for Modulating Polyproline Heikes 247
11.3.7 Pseudoprolines for Modulating Structure and Function of
Cyclosporins 249
11.3.8 Pseudoprolines for Targeting Cis Bonds in Peptides
and Proteins 251
11.4 Conclusions and Perspectives 252
12 Peptidyl Prolyl Isomerases: New Targets for Novel Therapeutics? 261
Christophe Dugave
12.1 Introduction 262
12.2 Implication of PPIases in Biological Processes and Diseases 262
12.2.1 PPIases and Protein Folding and Trafficking 262
12.2.2 Immunosuppressive Pathways Through Formation of
PPIase:Ligand Complexes 263
12.2.3 Modulation of Ion Channels by PPIases 265
12.2.4 Chaperone Activity of Immunophilins in Steroid Receptor
Signaling 265
12.2.5 Immunophilins and Neurodegenerative Disorders 266
12.2.6 PPIases and Cell Multiplication 267
12.2.7 Implication of PPIases in Apoptosis 270
12.2.8 PPIases and Infectious Diseases 270
12.3 Structure and SAR studies of PPIases: Structural Evidence and
Putative Catalytic Mechanism 272
12.3.1 Generalities 272
12.3.2 Cyclophilins and FKBPs: Similar Molecular Basis for
Distinct Catalytic Mechanisms 273
12.3.3 Parvulins 276
12.4 PPIase Inhibitors: From In Vitro Inhibitors to Novel
Therapeutics 277
12.4.1 Natural PPIase Inhibitors and Their Analogs 277
12.4.2 Mechanism-Based Inhibitors 282
X I Contents
12.4.3 Library Screening Versus in Silico Design: Current Status
and Future Prospects 284
12.5 Conclusion and Perspectives 288
13 Other Cis-Trans Isomerizations in Organic Molecules
and Biomolecules 295
Muriel Gondry and Christophe Dugave
13.1 Introduction 295
13.2 Cis-Trans Isomerization around Single Bonds 295
13.2.1 Cis-Trans Isomerism ofAryl Compounds 295
13.2.2 Disulfide Bonds 297
13.2.3 Amide Surrogates with Restricted Rotation of a oBond 298
13.3 C=N-containing Compounds 300
13.3.1 Oximes and Nitroso Compounds 300
13.3.2 Imines and Schiff Bases 300
13.4 Dehydroamino Acids and Dehydropeptides 303
13.4.1 Acryloyl Peptides, Acrylates and Related Molecules 303
13.4.2 Naturally Occurring Dehydroamino Acids and Dehydropeptides 305
13.4.3 Synthetic Dehydroamino Acids and Dehydropeptides 308
13.5 Phototunable Biomolecules Containing an Azobenzene Moiety 320
13.5.1 Phototunable Ligands 310
13.5.2 Phototunable Conformation of Peptides 312
13.5.3 Modifkations of Proteins with Photoisomerizable Motifs 313
13.5.4 Other Phototunable Biomolecules 315
14 Cis-Trans Isomerism in Metal Complexes 321
Alzir Azevedo Batista and Salete Linhares Queiroz
14.1 Introduction 321
14.1.1 Trans Effect 324
14.1.2 Protonation ofthe Leaving Group 326
14.1.3 Separation or Purification of Cis-Trans Isomers 327
14.1.4 Identification of Cis-Trans Isomers 327
14.2 The Cis-Trans Isomerization of Metal Complexes: Mechanisms and
Effects 330
14.2.1 Cis or Trans Isomer? 330
14.2.2 Isomerization Processes 331
14.3 Cis-Trans Isomers of Metal Complexes as Potential Therapeutics 334
14.4 Applications of Cis-Trans Isomerization of Metal Complexes in
Supramolecular Chemistry 337
14.5 Final Remarks 341
Index 345 |
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| id | DE-604.BV021791719 |
| illustrated | Illustrated |
| index_date | 2024-07-02T15:44:45Z |
| indexdate | 2024-07-09T20:44:43Z |
| institution | BVB |
| isbn | 9783527313044 3527313044 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-015004351 |
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| owner_facet | DE-703 DE-19 DE-BY-UBM DE-11 |
| physical | XV, 354 S. Ill., graph. Darst. 25 cm |
| publishDate | 2006 |
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| publisher | Wiley-VCH-Verl. |
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| spelling | Cis-trans isomerization in biochemistry ed. by Christophe Dugave Weinheim Wiley-VCH-Verl. 2006 XV, 354 S. Ill., graph. Darst. 25 cm txt rdacontent n rdamedia nc rdacarrier Literaturangaben Bioquímica larpcal Cis-trans isomérases Isomérisation Liaisons doubles (Chimie) Peptidylprolyl isomerase Biochemistry Biomolecules Isomerism Stereochemistry Biomolekül (DE-588)4135124-1 gnd rswk-swf cis-trans-Isomerie (DE-588)4148046-6 gnd rswk-swf Biomolekül (DE-588)4135124-1 s cis-trans-Isomerie (DE-588)4148046-6 s DE-604 Dugave, Christophe Sonstige oth text/html http://deposit.dnb.de/cgi-bin/dokserv?id=2774606&prov=M&dok_var=1&dok_ext=htm Inhaltstext HBZ Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=015004351&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Cis-trans isomerization in biochemistry Bioquímica larpcal Cis-trans isomérases Isomérisation Liaisons doubles (Chimie) Peptidylprolyl isomerase Biochemistry Biomolecules Isomerism Stereochemistry Biomolekül (DE-588)4135124-1 gnd cis-trans-Isomerie (DE-588)4148046-6 gnd |
| subject_GND | (DE-588)4135124-1 (DE-588)4148046-6 |
| title | Cis-trans isomerization in biochemistry |
| title_auth | Cis-trans isomerization in biochemistry |
| title_exact_search | Cis-trans isomerization in biochemistry |
| title_exact_search_txtP | Cis-trans isomerization in biochemistry |
| title_full | Cis-trans isomerization in biochemistry ed. by Christophe Dugave |
| title_fullStr | Cis-trans isomerization in biochemistry ed. by Christophe Dugave |
| title_full_unstemmed | Cis-trans isomerization in biochemistry ed. by Christophe Dugave |
| title_short | Cis-trans isomerization in biochemistry |
| title_sort | cis trans isomerization in biochemistry |
| topic | Bioquímica larpcal Cis-trans isomérases Isomérisation Liaisons doubles (Chimie) Peptidylprolyl isomerase Biochemistry Biomolecules Isomerism Stereochemistry Biomolekül (DE-588)4135124-1 gnd cis-trans-Isomerie (DE-588)4148046-6 gnd |
| topic_facet | Bioquímica Cis-trans isomérases Isomérisation Liaisons doubles (Chimie) Peptidylprolyl isomerase Biochemistry Biomolecules Isomerism Stereochemistry Biomolekül cis-trans-Isomerie |
| url | http://deposit.dnb.de/cgi-bin/dokserv?id=2774606&prov=M&dok_var=1&dok_ext=htm http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=015004351&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
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