Synthesis and Analytics of Rigidified Peptide Architectures. Neuropeptide Y Dipeptide Scan Ring-Chain-Equilibria of Iminopeptides Thiazole Amino Acids for Thiopeptide Antibiotics
Synthesis and Analytics of Rigidified Peptide Architectures. Neuropeptide Y Dipeptide Scan Ring-Chain-Equilibria of Iminopeptides Thiazole Amino Acids for Thiopeptide Antibiotics

Author: Sebastian Enck

Publisher: Logos Verlag Berlin GmbH

Published: 2010

Total Pages: 536

ISBN-13: 3832526129

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The architectures (three-dimensional shapes) of peptides determine their respective biological functions. Therefore, the correct alignment of functionalities in a structure by constraining the flexibility is a key process in evolution as well as in medicinal chemistry in order to increase binding affinity and selectivity. The rigidification of a peptide chain can have local effects (incorporation of the amino acid proline) or it can globally restrain flexibility (macrocyclization). Furthermore, the combination of both strategies has given rise to complex antibiotics with highly optimized modes of action. This work approaches these principles in three topics and for different purposes. The first chapter presents a novel scanning strategy which utilizes synthetic local rigidifications for the evaluation of Neuropeptide Y structure and receptor binding patterns. The fundamental process of macrocyclization is topic of the second chapter. For iminopeptides, ring-chain equilibria can be established and controlled, thereby allowing for the thermodynamic analysis of the ring closure. This leads to the identification of structural determinants that influence the inclination of a peptide chain to close the ring. In the third chapter, a sugarbased synthetic pathway leading to highly functionalized thiazole dipeptides is described. This strategy led to the synthesis of core motivs of complex thiopeptide antibiotics, as well as to diastereomers and homologs thereof.

Chemical Approaches to the Synthesis of Peptides and Proteins
Chemical Approaches to the Synthesis of Peptides and Proteins

Author: Paul Lloyd-Williams

Publisher: CRC Press

Published: 1997-04-23

Total Pages: 306

ISBN-13: 9780849391422

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Organic chemists working on the synthesis of natural products have long found a special challenge in the preparation of peptides and proteins. However, more reliable, more efficient synthetic preparation methods have been developed in recent years. This reference evaluates the most important synthesis methods available today, and also considers methods that show promise for future applications. This text describes the state of the art in efficient synthetic methods for the synthesis of both natural and artificial large peptide and protein molecules. Subjects include an introduction to basic topics, linear solid-phase synthesis of peptides, peptide synthesis in solution, convergent solid-phase synthesis, methods for the synthesis of branched peptides, formation of disulfide bridges, and more. The book emphasizes strategies and tactics that must be considered for the successful synthesis of peptides.

The Peptides Analysis, Synthesis, Biology
The Peptides Analysis, Synthesis, Biology

Author: Erhard Gross

Publisher: Elsevier

Published: 2012-12-02

Total Pages: 330

ISBN-13: 0323155634

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The Peptides: Analysis, Synthesis, Biology: Volume 4: Modern Techniques of Conformational, Structural, and Configurational Analysis is an open-ended treatise that provides comprehensive and critical reviews of important developments in all areas of peptide research including analysis, synthesis, and biology. X-ray structure studies, amino acid analysis, and chiroptical analysis of configuration are discussed, along with solid-phase sequencing and ultramicroanalysis with the aid of fluorescence. This volume is comprised of six chapters and begins with an account of crystal structure analysis on molecules containing 2-12 peptide units, focusing on the variety of intramolecular hydrogen bonds, cis peptide units, and multiple conformation. Conformational changes upon complexation with metal ions are considered, together with the inclusion of solvents as integral parts of a molecular structure. The following chapters explore the conformations of insulin, glucagon, pancreatic polypeptide and related molecules, as well as the molecular biology of these hormones based on crystal structures; the usefulness of chiroptical techniques for determining the absolute configuration of amino acids and small peptides; and ultramicroanalysis of peptides and proteins by high performance liquid chromatography and fluorescence detection. The final chapter looks at the status and future potential of solid-phase sequencing. This book is intended as a reference for specialists, a guide for the novice, and a forum for investigators concerned with research on peptides and proteins.

Studies on Chemical Synthesis of Peptides: Efficient Synthetic Methods for β-Amino Acids, Azides, Amino Acid Hydroxamates and Esters
Studies on Chemical Synthesis of Peptides: Efficient Synthetic Methods for β-Amino Acids, Azides, Amino Acid Hydroxamates and Esters

Author: Vasanthakumar Ganga Ramu

Publisher: GRIN Verlag

Published: 2011-10-17

Total Pages: 186

ISBN-13: 3656030456

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Doctoral Thesis / Dissertation from the year 2004 in the subject Chemistry - Organic Chemistry, Bangalore University / Central College (Department of Studies in Chemistry), language: English, abstract: The importance of ß-amino acids has been focused, particularly in the past few decades. They are found as components of many biologically active peptidic and nonpeptidic natural products with antibiotic, antifungal, cytotoxic, and other pharmacological properties. ß-Amino acids are produced in humans, animals, microorganisms, marine organisms, and plants either in free state or as part of a peptide or depsipeptide. The importance of nonpeptidic ß-amino acids has been nfocused particularly on the ß-lactam antibiotics, since naturally occurring penicillin derivatives have been discovered as broad antibiotic active agents. Over the years, a large number of these compounds have been prepared and tested, and a variety of new ß-lactam ring systems have been introduced such as cephems, cephalosporins, oxacephems, penems, carbapenems, oxapenams as well as monocyclic and polycyclic ring systems. ß-Amino acids have been known to play an important role in primary and secondary metabolism also. [...]

Principles of Peptide Synthesis
Principles of Peptide Synthesis

Author: Miklos Bodanszky

Publisher: Walter de Gruyter GmbH & Co KG

Published: 1984-12-31

Total Pages: 324

ISBN-13: 3112728718

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No detailed description available for "Principles of Peptide Synthesis".

Major Methods of Peptide Bond Formation
Major Methods of Peptide Bond Formation

Author: Erhard Gross

Publisher: Elsevier

Published: 2014-05-10

Total Pages: 454

ISBN-13: 1483217965

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The Peptides: Analysis, Synthesis, Biology, Volume 1: Major Methods of Peptide Bond Formation provides comprehensive and critical reviews of important developments in three major areas of peptide research—analysis, synthesis, and biology. This book discusses the nature of the peptide bond, coupling between amino acid residues, and catalysis of active ester reactions. The formation of hydrazides, reactions of carbodiimides with amines, and mixed carbonic anhydride method of peptide synthesis are also elaborated. This publication likewise covers the control of racemization during peptide synthesis, strategies for minimizing racemization during amide-forming steps, and assays for chiral purity. This volume is suitable for students, specialists, and scientists from a broad range of disciplines concerned with peptides.

Side Reactions in Peptide Synthesis
Side Reactions in Peptide Synthesis

Author: Yi Yang

Publisher: Academic Press

Published: 2015-09-01

Total Pages: 378

ISBN-13: 0128011815

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Side Reactions in Peptide Synthesis, based on the author's academic and industrial experience, and backed by a thorough review of the current literature, provides analysis of, and proposes solutions to, the most frequently encountered side reactions during peptide and peptidomimetic synthesis. This valuable handbook is ideal for research and process chemists working with peptide synthesis in diverse settings across academic, biotech, and pharmaceutical research and development. While peptide chemistry is increasingly prevalent, common side reactions and their causes are often poorly understood or anticipated, causing unnecessary waste of materials and delay. Each chapter discusses common side reactions through detailed chemical equations, proposed mechanisms (if any), theoretical background, and finally, a variety of possible solutions to avoid or alleviate the specified side reaction. - Provides a systematic examination on how to troubleshoot and minimize the most frequent side reactions in peptide synthesis - Gives chemists the background information and the practical tools they need to successfully troubleshoot and improve results - Includes optimization-oriented analysis of side reactions in peptide synthesis for improved industrial process development in peptidyl API (active pharmaceutical ingredient) production - Answers the growing, global need for improved, replicable processes to avoid impurities and maintain the integrity of the end product. - Presents a thorough discussion of critical factors in peptide synthesis which are often neglected or underestimated by chemists - Covers solid phase and solution phase methodologies, and provides abundant references for further exploration

The Peptides
The Peptides

Author: Eberhard Schröder

Publisher: Elsevier

Published: 2014-05-12

Total Pages: 512

ISBN-13: 1483261727

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The Peptides, Volume I: Methods of Peptide Synthesis focuses on detailed description of protecting groups, individual amino acids, and coupling reactions. The publication first offers information on amino-protecting and carboxyl-protecting groups, including carboxyl protection by salt formation, esterification, and amide formation and acyl-type, alkyl-type, and urethane protecting groups. The text then examines the formation of the peptide bond and amino acids. Discussions focus on amino acids with the alcoholic hydroxyl group, sulfur amino acids, basic and acidic amino acids, synthesis of peptides by activation of the amino group, and peptide synthesis by activation of the carboxyl group. The manuscript elaborates on the synthesis of cyclic peptides, depsipeptides, peptoids, and the plastein reaction. Topics include synthesis of plastein-active peptides, glycopeptides, phosphopeptides, and S-peptides. The publication is a dependable source of data for readers interested in the methods of peptide synthesis.

Peptide Chemistry
Peptide Chemistry

Author: Miklos Bodanszky

Publisher: Springer Science & Business Media

Published: 2012-12-06

Total Pages: 207

ISBN-13: 364278206X

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A continued interest in Peptide Chemistry prompted the revision of the first edition of this book. This provided an opportunity to update several details. I am grateful to colleagues who were kind enough to inform me of errors, typographical and other, they had discovered in the first edi tion. These have now been corrected, as were certain shortcomings in language and style pointed out by my daughter, Dr. Eva Bodanszky. In 1991 the excellent The Chemical Synthesis of Peptides by John Jones (Oxford University Press, 1991) appeared. It covers, in part, the same field, but is different enough from Peptide Chemistry, to justify publication of a revised edition of the latter. Princeton, July 1993 M. Bodanszky Preface to the First Edition Nature applied peptides for a great variety of specific functions. The specificity provided by the individual character of each amino acid is further ehanced by the combination of several amino acids into larger molecules. Peptides therefore can act as chemical messengers, neuro transmitters, as highly specific stimulators and inhibitors, regulating var ious life-processes. Entire classes of biologically active compounds, such as the opioid peptides or the gastrointestinal hormones emerged within short periods of time and it is unlikely that the rapid succession of discoveries of important new peptides would come to a sudden halt. In fact, our knowledge of the field is probably still in an early stage of development. Peptides also gained importance in our everyday life.