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Main description:
Many physiologically important receptors and enzymes are regulated by their endogenous ligands and inhibitors. Nature chose to utilize these p- tides as chemical switches since they can be efficiently synthesized and - graded in cells, thus providing an immediate response to a fast changing environment. Such properties, so critical in cell survival, make peptides less than ideal drug candidates. Other frequently desired properties in drug m- ecules include oral bioavailability, the ability to cross membranes, including the blood-brain barrier, and sufficient stability for administration 1-2 times a day. In spite of these obstacles, some natural peptides and proteins are ind- putably successful medicines and have become drugs of choice. Further - vances in peptide-based pharmaceuticals are critically dependent on both new delivery methods and new chemical approaches to the conversion of these molecules to druglike entities. In addition, peptides are also the natural sta- ing points for optimization of their pharamacological and chemical prop- ties, which may lead to superior drugs. Peptidomimetics Protocols deals with both aspects of peptide pharmaceuticals, through the tools of modern s- thetic and medicinal chemistry. The last decade has witnessed a steady stream of new synthetic approaches to peptide mimetics, compounds that replace phy- ologically vulnerable peptide functionalities with chemical modules of - creased stability and cellular penetration. The chapters have been written by both academic and industrial chemists, and focus on the practical synthetic preparation of peptide mimetics.
Contents:
Synthesis and Use of Pseudopeptides Derived from 1,2,4-Oxadiazole-, 1,3,4-Oxadiazole-, and 1,2,4-Triazole-based Dieptidomimetics, Kristina Luthman, Susanna Borg, and Uli Hacksell. Syntheses of FMOC-2,3-Methanoleucine Stereoisomers and their Incorporation into Peptidomimetics, Kevin Burgess and Wen Li. Synthesis of an Esterase-Sensitive Cyclic Prodrug of a Model Hexapeptide Having Enhanced Membrane Permeability and Enzymatic Stability Using an Acyloxyalkoxy Promoiety, Sanjeev Gangwar, Giovanni M. Pauletti, Teruna J. Siahaan, Valentino J. Stella, and Ronald T. Borchardt. Synthesis of an Esterase-Sensitive Cyclic Prodrug of a Model Hexapeptide Having Enhanced Membrane Permeability and Enzymatic Stability Using a 3-(2'-Hydroxy-4',6'-Dimethylphenyl)-3,3-Dimethyl Propionic Acid Promoiety, Binghe Wang, Sanjeev Gangwar, Giovanni Pauletti, Teruna Siahaan, and Ronald T. Borchardt. Synthesis of Coumarin-Based, Esterase-Sensitive Cyclic Prodrugs of Opioid Peptides with Enhanced Membrane Permeability and Enzymatic Stability, Binghe Wang, Daxian Shan, Wei Wang, Huijuan Zhang, Olafur Gudmundsson, and Ronald T. Borchardt. Azatides as Peptidomimetics: Solution and Liquid Phase Syntheses, Hyunsoo Han, Juyoung Yoon, and Kim D. Janda. Synthesis of Cbz-Protected Ketomethylene Dipeptide Isosteres, Robert V. Hoffman and Junhua Tao. (E)-Alkene Peptide Bond Isosteres by Cuprate Opening of Vinyl Aziridines, Todd C. Henninger and Peter Wipf. Syntheses of Norstatine, Its Analogs, and Dipeptide Isosteres by Means of ss-Lactam Synthon Method, Iwao Ojima and Francette Delaloge. Synthesis of a Versatile Peptidomimetic Scaffold, Stephen Hanessian and Grant McNaughton-Smith. An Asymmetric Synthesis Protocol to Prepare Topographically Constrained ss-Substituted Aromatic Amino Acids, Subo Liao and Victor J. Hruby. Synthesis of Oligopeptides Containing an Oxirane Ring in the Place of a Peptidic Bond, Maurizio Taddei. Synthesis of Protected Lactam-Bridged Dipeptides, Debra S. Perlow and Roger M.Freidinger. Synthesis of Peptidomimics Through Sugar-Based Scaffolds, Yves Le Merrer, Lydie Poitout, and Jean-Claude Depezay. The Synthesis of Bicyclic Piperazinone and Related Derivatives, Yvette M. Fobian and Kevin D. Moeller. Synthesis of Dipeptides with y[CH2O] Amide Bond Mimetics, Wieslaw M. Kazmierski and Paul C. Fritch. SNAr-Based Cycloetherification Methodology: Application in the Synthesis of Heterodectic Macrocyclic Peptides with Endo Aryl-Aryl and Aryl-Alkyl Ether Bonds, Jieping Zhu. Cyclic Aromatic Amino Acids with Constrained c1 and c2 Dihedral Angles, Dirk Tourwe, Koen Iterbeke, Wieslaw M. Kazmierski, and Geza Toth. Asymmetric Syntheses of Unnatural Amino Acids and Hydroxyethylene Peptide Isosteres, Robert M. Williams. Fluoroolefin Isosteres, J.T. Welch and T. Allmendinger. Synthesis of 3-Amino-1-Carboxymethyl-Benzodiazepine (BZA) Peptidomimetics, James C. Marsters, Jr. and Thomas E. Rawson. A Conformationally Restricted ss-Strand HIV Protease Inhibitor, Michael C. Hillier and Stephen F. Martin. Synthesis of Cyclopropane-Containing Leu-Enkephalin Analogs, Michael P. Dwyer and Stephen F. Martin. The 1,5-Disubstituted Tetrazole Ring as a cis-Amide Bond Surrogate, Janusz Zabrocki and Garland R. Marshall. Synthesis of (2R, 3R, 4R, 5S)-5-tert- Butyloxycarbonylamino-3,4-Dihydroxy-2-Isopropyl-3,4-O,O-Isopropylidene-6-Cyclohexyl-Hexanoic Acid, Allen Scott, Brian G. Conway, and Mark A. Krook. Synthesis of (2S, 4S, 5S)-5-(t-Butoxycarbonylamino)- 4-(t-Butyldimethylsilyloxy)-2-Isopropyl-7-Methyl Octanoic Acid, Mark A. Lyster and Brian G. Conway. Synthesis of a-Vinyl Amino Acids, David B. Berkowitz, Jill M. McFadden, Marianne K. Smith, and Michelle L. Pedersen. A Novel Synthetic Protocol for the Preparation of Enantiopure 3-, 4-, and 5-Substituted Prolines, N. Andre Sasaki. Synthesis of Aminobenzoic Acid-Based Nonpeptide Templates: Applications in Peptidomimetic Drug Discovery, Kimberly S. Para and Tomi K. Sawyer. Aminimides as Peptidomimetics,
PRODUCT DETAILS
Publisher: Springer (Humana Press Inc.)
Publication date: November, 2010
Pages: 576
Weight: 842g
Availability: Available
Subcategories: Biochemistry
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