Cis–trans Isomerization in Biochemistry

Christophe Dugave prepared his PhD in molecular pharmacology under the guidance of Professor Marquet and Professor Gaudry. Then he moved to the University of Sherbrooke (Canada) where he worked as a post-doctoral fellow under the supervision of Professor Deslongchamps. He is currently working at the Department of Protein Engineering and Research of the French Atomic Energy Commission at CEA/Saclay near Paris. His research interests include the synthesis of nonnatural amino acids, pseudopeptides, peptidomimetics, and radiolabeling of peptides and proteins with tritium technetium and other radioisotopes.

Preface.List of Contributors.1 Nomenclature (Christophe Dugave).2 General Mechanisms of Cis-Trans Isomerization: A Rapid Survey (Christophe Dugave).2.1 Introduction.2.2 Homolytic Cis-Trans Isomerization.2.3 Heterolytic Cis-Trans Isomerization.3 Mechanisms of Cis-Trans Isomerization around the Carbon-Carbon Double Bonds via the Triplet State (Yasushi Koyama, Yoshinori Kakitani, and Hiroyoshi Nagae).3.1 A Concept of a Triplet-Excited Region.3.2 Triplet-State Isomerization in Retinal.3.3 Triplet-State Isomerization in b-Carotene and Spheroidene.3.4 Spectroscopic and Analytical Techniques for Studying Cis-Trans Isomerization in the T1 State.4 Retinal Binding Proteins (Hideki Kandori).4.1 Retinal Chromophore in Rhodopsins.4.2 Photoisomerization in Visual Rhodopsins.4.3 Photoisomerization in Archaeal Rhodopsins.4.4 Summary and Prospects.5 Non-Retinal Chromophoric Proteins (Marc Zimmer).5.1 Introduction.5.2 Photoactive Yellow Protein.5.3 Green Fluorescent Protein and Other GFP-like Proteins.5.4 Phytochromes.6 Fatty Acids and Phospholipids (Chryssostomos Chatgilialoglu and Carla Ferreri).6.1 Introduction.6.2 Enzyme-Catalyzed Cis-Trans Isomerization of Unsaturated Fatty Acid Residues in Bacteria.6.3 Radical-Catalyzed Cis-Trans Isomerization of Unsaturated Lipids and its Effect on Biological Membranes.6.4 Perspectives and Future Research.7 In Silico Dynamic Studies of Cis-Trans Isomerization in Organic and Biological Systems (Ute F. R!hrig, Ivano Tavernelli, and Ursula Rothlisberger).7.1 Introduction.7.2 Computational Methods.7.3 Theoretical Aspects of CTI.7.4 CTI in PSB5 and Formaldimine.7.5 CTI in Rhodopsin.7.6 Summary and Conclusions.8 Chemical Aspects of the Restricted Rotation of Esters, Amides, and Related Compounds (Christophe Dugave).8.1 Thermodynamic and Kinetic Aspects of Cis-Trans Isomerization.8.2 Influence of the Environment on CTI.8.3 The Study of CTI of Amides and other Conjugated p-Systems.9 Amide Cis-Trans Isomerization in Peptides and Proteins (Stephan Wawra and Gunter Fischer).9.1 Imidic and Secondary Amide Peptide Bond Conformation.9.2 Amide Relevant Conformations in Proteins.9.3 Native State Peptide Bond Isomerization.9.4 Biological Consequences.10 Enzymes Catalyzing Peptide Bond Cis-TransIsomerizations (Gunter Fischer).10.1 Introduction.10.2 Cyclophilins.10.3 FK506 Binding Proteins (FKBPs).10.4 Trigger Factor.10.5 Parvulins.10.6 Secondary Amide Peptide Bond Cis-Trans Isomerases.10.7 Catalytic Mechanism of Peptide Bond Cis-Trans Isomerases.11 Tailoring the Cis-Trans Isomerization of Amides (Luis Moroder and Christian Renner, John J. Lopez, Gabriele Tuchscherer and Manfred Mutter).11.1 Introduction.11.2 Substituted Prolines.11.3 Pseudoprolines in Chemical Synthesis and Biology.11.4 Conclusions and Perspectives.12 Peptidyl Prolyl Isomerases: New Targets for Novel Therapeutics? (Christophe Dugave).12.1 Introduction.12.2 Implication of PPIases in Biological Processes and Diseases.12.3 Structure and SAR studies of PPIases: Structural Evidence and Putative Catalytic Mechanism.12.4 PPIase Inhibitors: From In Vitro Inhibitors to Novel Therapeutics.12.5 Conclusion and Perspectives.13 Other Cis-Trans Isomerizations in Organic Molecules and Biomolecules (Muriel Gondry and Christophe Dugave).13.1 Introduction.13.2 Cis-Trans Isomerization around Single Bonds.13.3 C=N-containing Compounds.13.4 Dehydroamino Acids and Dehydropeptides.13.5 Phototunable Biomolecules Containing an Azobenzene Moiety.14 Cis-Trans Isomerism in Metal Complexes (Alzir Azevedo Batista and Salete Linhares Queiroz).14.1 Introduction.14.2 The Cis-Trans Isomerization of Metal Complexes: Mechanisms and Effects.14.3 Cis-Trans Isomers of Metal Complexes as Potential Therapeutics.14.4 Applications of Cis-Trans Isomerization of Metal Complexes in Supramolecular Chemistry.14.5 Final Remarks.Index.