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Side Reactions In Peptide Synthesis

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Side Reactions in Peptide Synthesis

Side Reactions in Peptide Synthesis Book
Author : Yi Yang
Publisher : Academic Press
Release : 2015-09-01
ISBN : 0128011815
Language : En, Es, Fr & De

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Book Description :

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

Chemistry of Peptide Synthesis

Chemistry of Peptide Synthesis Book
Author : N. Leo Benoiton
Publisher : CRC Press
Release : 2005-08-12
ISBN : 9781574444544
Language : En, Es, Fr & De

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Book Description :

Chemistry of Peptide Synthesis is a complete overview of how peptides are synthesized and what techniques are likely to generate the most desirable reactions. Incorporating elements from the author’s role of Career Investigator of the Medical Research Council of Canada and his extensive teaching career, the book emphasizes learning rather than memorization. The text uses clear language and schematics to present concepts progressively, carefully excluding unnecessary details and providing a historical context in which to appreciate the development of the field. The author first outlines the fundamentals of peptide synthesis, focusing on the intermediates in aminolysis reactions. Gradually the text builds into discussions of the applicability of coupling reactions, stereomutation, methods of deprotection, solid-phase synthesis, side-chain protection and side reactions, and amplification on coupling methods. The book clarifies the differences between oxazolones from amino-acid derivatives and segments and the implications of their formation on the chiral integrity of products. The author offers a critical analysis of the mechanisms of coupling reactions and the desirability of preactivation. The text explains hindrance and the nucleophilicity of tertiary amines and rationalizes their use. The book also explores mechanisms of acidolysis and the dual role of nucleophiles as reactants and scavengers. Chemistry of Peptide Synthesis supplies a broad, yet straightforward approach that appeals to those with limited knowledge of organic chemistry or chemists from other fields as well as in-depth coverage that can be appreciated by experienced peptidologists.

Principles of Peptide Synthesis

Principles of Peptide Synthesis Book
Author : M. Bodanszky
Publisher : Springer Science & Business Media
Release : 2012-12-06
ISBN : 3642967639
Language : En, Es, Fr & De

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Book Description :

A look at the shelves of a major library awakens doubts in the author of this small volume about the importance of writing a new introduction to peptide synthesis. This rather narrow area of bio-organic chemistry already has received considerable attention. A whole series of books deals with the synthesis of peptides. Some of these are textbooks written to support lecture courses on peptide synthesis. Others try to help the beginner, otherwise well versed in organic chemistry, to embark on some experimental project that requires the construction of peptide chains. Not less useful are the monographs which were compiled to aid the adept practitioner and to provide him with references to the growing literature of a very active field. Is there any need for a new book on peptide synthesis? Should we add a new volume to an already impressive and certainly useful series? The answer is not obvious. The author has already participated in two similar en deavors. The first edition! of "Peptide Synthesis", with M. A. Ondetti as coauthor, was meant to serve as an introduction for the beginner. It was rather well received by researchers who joined the field of peptide chemistry and were looking for initiation. While working on the 2 second edition with Drs. Klausner and Ondetti, we became painfully aware of the impossibility of the task.

Major Methods of Peptide Bond Formation

Major Methods of Peptide Bond Formation Book
Author : Erhard Gross,Johannes Meienhofer
Publisher : Elsevier
Release : 2014-05-10
ISBN : 1483217965
Language : En, Es, Fr & De

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Book Description :

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.

Chemical Approaches to the Synthesis of Peptides and Proteins

Chemical Approaches to the Synthesis of Peptides and Proteins Book
Author : Paul Lloyd-Williams,Fernando Albericio,Ernest Giralt
Publisher : CRC Press
Release : 2020-08-18
ISBN : 1000151689
Language : En, Es, Fr & De

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Book Description :

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

The Peptides Book
Author : Eberhard Schröder,Klaus Lübke
Publisher : Elsevier
Release : 2014-05-12
ISBN : 1483261727
Language : En, Es, Fr & De

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Book Description :

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.

Aspects of the Merrifield Peptide Synthesis

Aspects of the Merrifield Peptide Synthesis Book
Author : C. Birr
Publisher : Springer Science & Business Media
Release : 2012-12-06
ISBN : 3642670040
Language : En, Es, Fr & De

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Book Description :

This book was written in the context of the daily confrontation with problems in the utilization of polymeric supports for the synthesis of pep tides. Therefore, views and experiences which usually are not mentioned in scientific journals are collected in these pages. The author has deliberately discussed in detail the possible influence of the polymer phase on the varying reaction conditions in the Merrifield synthesis; this aspect is neglected in most publications dealing with peptide synthesis. However, in view of the growing body of information on the chemistry of polymer-supported peptide syntheses, the international readership should regard the author's arguments as open to discussion. I am very much indebted to all of my colleagues with whom I have had the opportunity to cooperate in studying the potential of the Merrifield synthesis. Above all I like to express my gratitude to my teacher, Professor Dr. Theodor Wieland, Heidelberg, for his boundless encouragement and support in my ef forts in the field of peptide synthesis, particularly in its polymer phase bound version. Last but not at least I wish to thank Miss Hildegard Leyden. With in finite patience and great accuracy she typed the manuscript in addition to her daily duties. The work which influenced this book was performed under the auspices of the Max-Planck-Gesellschaft, of which the financial support is gratefully ac knowledged.

The Peptides Special methods in peptide synthesis pt A

The Peptides  Special methods in peptide synthesis  pt  A Book
Author : Erhard Gross,Johannes Meienhofer
Publisher : Unknown
Release : 1979
ISBN : 0987650XXX
Language : En, Es, Fr & De

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Book Description :

Download The Peptides Special methods in peptide synthesis pt A book written by Erhard Gross,Johannes Meienhofer, available in PDF, EPUB, and Kindle, or read full book online anywhere and anytime. Compatible with any devices.

Amino Acid and Peptide Synthesis

Amino Acid and Peptide Synthesis Book
Author : John Jones
Publisher : Oxford University Press, USA
Release : 1992
ISBN : 0987650XXX
Language : En, Es, Fr & De

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Book Description :

The principal methods for the synthesis of amino acids and peptides are outlined in this concise introduction. With its emphasis on chemical principles and strategies, the book should be of value to all undergraduate chemistry students.

The World of Peptides

The World of Peptides Book
Author : Theodor Wieland,Miklos Bodanszky
Publisher : Springer Science & Business Media
Release : 2012-12-06
ISBN : 3642758509
Language : En, Es, Fr & De

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Book Description :

Almost two centuries ago proteins were recognized as the primary materials (proteios = primary) oflife, but the significance and wide role of peptides (from pepsis = digestion) in practically all life pro cesses has only become apparent in the last few decades. Biologi cally active peptides are now being discovered at rapid intervals in the brain and in other organs including the heart, in the skin of amphibians and many other tissues. Peptides and peptide-like compounds are found among toxins and antibiotics. It is unlikely that this process, an almost explosive broadening of the field, will come to a sudden halt. By now it is obvious that Nature has used the combination of a small to moderate number of amino acids to generate a great variety of agonists with specific and often highly sophisticated functions. Thus, peptide chemistry must be regarded as a discipline in its own right, a major branch of biochemistry, fairly separate from the chemistry of proteins. Because of the important role played by synthesis both in the study and in the practical preparation of peptides, their area can be considered as belonging to bio-organic chemistry as well. The already overwhelming and still increasing body of know ledge renders an account of the history of peptide chemistry more and more difficult. It appears therefore timely to look back, to take stock and to recall the important stages in the development of a new discipline.

Peptide Chemistry

Peptide Chemistry Book
Author : Miklos Bodanszky
Publisher : Springer Science & Business Media
Release : 2012-12-06
ISBN : 364278206X
Language : En, Es, Fr & De

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Book Description :

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.

Protection of Functional Groups in Peptide Synthesis

Protection of Functional Groups in Peptide Synthesis Book
Author : Erhard Gross,Johannes Meienhofer
Publisher : Elsevier
Release : 2014-05-10
ISBN : 1483217981
Language : En, Es, Fr & De

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Book Description :

The Peptides: Analysis, Synthesis, Biology, Volume 3: Protection of Functional Groups in Peptide Synthesis focuses on protection of functional groups in peptide synthesis. This book consists of seven chapters. Chapter 1 reviews the large variety of amine protecting groups. The protection of carboxyl groups is described in Chapter 2, while the chemistry of sulfhydryl group protection in peptide synthesis is discussed in Chapter 3. Chapter 4 covers the protection of the hydroxyl groups of serine, threonine, tyrosine, and other hydroxyl-containing amino acids. Differential protection and selective deprotection in peptide synthesis is deliberated in Chapter 5. In chapter 6, the opportunities and constraints of the tactics of minimal protection of side-chain functions during peptide synthesis are reviewed. The last chapter is devoted to the interesting aspects of dual function groups. This volume is recommended for specialists and researchers concerned with peptide and protein research.

The Chemical Synthesis of Peptides

The Chemical Synthesis of Peptides Book
Author : John Jones,Lecturer in Organic Chemistry and Official Fellow and Tutor of Balliol College Dean John Jones
Publisher : Oxford University Press
Release : 1991
ISBN : 0987650XXX
Language : En, Es, Fr & De

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Book Description :

Peptides have many roles in medicine, and their potential for future application is even greater. They are involved in the regulation of fertility, the control of pain, the stimulation of growth, cancer therapy, cardiovascular problems, connective tissue diseases, digestive disorders, mental illness, and infections by microbial or viral agents. The preparation of such compounds by manipulating biological systems (genetic engineering) is an increasingly sophisticated art, but each case requires developmental work, and the approach is at present almost powerless with structural types that don't occur naturally. Chemical synthesis, on the other hand, is in principle applicable to any target, and is likely to remain very important in the peptide area for the foreseeable future. The emphasis throughout this book is on the chemical principles behind the more important methods of peptide synthesis. It provides a critical, concise, and up-to-date survey of the field. The term peptide is interpreted liberally, as embracing not only conventional sequences of up to a few dozen natural amino acids, but also protein-scale molecules and structures comprising other residues or unusual features, for example, cyclopeptides and conjugated peptides. The synthetic methods considered here are treated within a modern mechanistic framework, and illustrated with carefully selected case studies, and this valuable account will be of interest to all those working in the field of peptide synthesis.

Part I Application of 2 Hydroxymethylacrylic Acid a Product of Baylis Hillman Reaction for the Synthesis of Novel N backbone to Side Chain Cyclic Peptide Analogs Strategies and Side Reactions Part II Synthesis and Biological Activities of Chimeric Bioactive Peptides Featuring Amino Acids Coupled to 4 Anilino N Phenethyl Piperidine

Part I  Application of 2 Hydroxymethylacrylic Acid  a Product of Baylis Hillman Reaction  for the Synthesis of Novel N backbone to Side Chain Cyclic Peptide Analogs  Strategies and Side Reactions Part II  Synthesis and Biological Activities of Chimeric Bioactive Peptides Featuring Amino Acids Coupled to 4 Anilino N Phenethyl Piperidine Book
Author : Ravil Rashitovich Petrov
Publisher : Unknown
Release : 2007
ISBN : 0987650XXX
Language : En, Es, Fr & De

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Book Description :

During my research career in Prof. V.J. Hruby's laboratory I worked on two different projects. The first project, which was initiated by the author, was planned to serve the need of our laboratory for a novel method of peptide cyclization. This method was planned to use recent advances in Pd0-catalyzed asymmetric synthesis combined with the structural richness offered by the Baylis-Hillman chemistry which could open new ways to diverse areas of drug design, molecular immunology and chemotherapy. This approach would provide cyclic peptides featuring N-alkylated amino acids that would confer high resistance to degradation by proteases. Because of numerous synthetic problems imposed, this strategy was not of considerable current use in peptide synthesis, especially on solid supports. However, despite a substantial amount of effort invested, this method faced serious drawbacks such as multistep synthesis and side reactions when applied to solid supports. Moreover, recent introduction of microwave technology which has helped to solve a great number of problems has led to a renaissance in the classical lactam and thioester bond cyclizations which overshadowed our quest for a novel methodology. The second project was focused on application of 4-anilidopiperidines for the synthesisof chimeric bioactive peptides. It was an effort towards the development of novel analgesics with reduced toxicity and enhanced potency. This project linked small molecule and multimeric ligand designs that were ongoing in our laboratory at the time. Major accomplishments in this project were made possible by successful resolution of several research challenges. I was able to find a straightforward, convenient and economical approach for the synthesis of novel analogues on a solid support. These developments led to novel compounds which showed substantial increases in their binding affinity relative to corresponding opioid analogues. To illustrate, compounds PET25, 26, 27, 29, 30, 31, and 32 showed high bioactivity and sub-nanomolar binding affinity to opioid receptors. Most of the peptides generated in the second project are still being investigated for their biological activities by our colleagues at the Department of Pharmacology, but the results to date indicate that some highly potent novel compounds have been made.

Special Methods in Peptide Synthesis

Special Methods in Peptide Synthesis Book
Author : Erhard Gross,Johannes Meienhofer
Publisher : Unknown
Release : 1983
ISBN : 9780123042057
Language : En, Es, Fr & De

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Book Description :

Download Special Methods in Peptide Synthesis book written by Erhard Gross,Johannes Meienhofer, available in PDF, EPUB, and Kindle, or read full book online anywhere and anytime. Compatible with any devices.

Principles of Peptide Synthesis

Principles of Peptide Synthesis Book
Author : M. Bodanszky
Publisher : Springer
Release : 1984-01-01
ISBN : 9783540123958
Language : En, Es, Fr & De

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Book Description :

A look at the shelves of a major library awakens doubts in the author of this small volume about the importance of writing a new introduction to peptide synthesis. This rather narrow area of bio-organic chemistry already has received considerable attention. A whole series of books deals with the synthesis of peptides. Some of these are textbooks written to support lecture courses on peptide synthesis. Others try to help the beginner, otherwise well versed in organic chemistry, to embark on some experimental project that requires the construction of peptide chains. Not less useful are the monographs which were compiled to aid the adept practitioner and to provide him with references to the growing literature of a very active field. Is there any need for a new book on peptide synthesis? Should we add a new volume to an already impressive and certainly useful series? The answer is not obvious. The author has already participated in two similar en deavors. The first edition! of "Peptide Synthesis", with M. A. Ondetti as coauthor, was meant to serve as an introduction for the beginner. It was rather well received by researchers who joined the field of peptide chemistry and were looking for initiation. While working on the 2 second edition with Drs. Klausner and Ondetti, we became painfully aware of the impossibility of the task.

The Peptides Protection of functional groups in peptide synthesis

The Peptides  Protection of functional groups in peptide synthesis Book
Author : Erhard Gross,Johannes Meienhofer
Publisher : Unknown
Release : 1979
ISBN : 0987650XXX
Language : En, Es, Fr & De

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Book Description :

Download The Peptides Protection of functional groups in peptide synthesis book written by Erhard Gross,Johannes Meienhofer, available in PDF, EPUB, and Kindle, or read full book online anywhere and anytime. Compatible with any devices.

Part 1 Solid Phase Synthesis of Oligonucleotides by the Phosphotriester Method

Part 1  Solid Phase Synthesis of Oligonucleotides by the Phosphotriester Method Book
Author : Denis Bernard Scanlon
Publisher : Unknown
Release : 1984
ISBN : 0987650XXX
Language : En, Es, Fr & De

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Book Description :

Download Part 1 Solid Phase Synthesis of Oligonucleotides by the Phosphotriester Method book written by Denis Bernard Scanlon, available in PDF, EPUB, and Kindle, or read full book online anywhere and anytime. Compatible with any devices.

Synthetic Peptides

Synthetic Peptides Book
Author : Gregory A. Grant
Publisher : Oxford University Press on Demand
Release : 2002
ISBN : 0195132610
Language : En, Es, Fr & De

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Book Description :

The first synthetic peptides were produces a century ago. In the ensuing period, they have developed as valuable research tools that are readily available to all researchers. However, since most reasearchers do not make their own peptides, they are often unfamiliar with not only the synthetic chemistry, but also with important and useful aspects of design, analysis, handling, and applications. This volume is written by experts in the field who provide detailed descriptions as well as practical advice for producing and using synthetic peptides. Chapters cover peptide design considerations, the synthetic chemistry, the evaluation of the synthetic product,and the modern applications of synthetic peptides. (Midwest).

Peptide Synthesis and Applications

Peptide Synthesis and Applications Book
Author : John Howl
Publisher : Springer Science & Business Media
Release : 2005
ISBN : 1592598773
Language : En, Es, Fr & De

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Book Description :

In this book, a panel of expert researchers and established group leaders describe in step-by-step detail the key methodologies of contemporary peptide systhesis and illustrate numerous applications that employ peptides as unique and essential materials. Techniques presented include protocols for chemical ligation, the systhesis of cyclic and phosphotyrosine-containing peptides, lipoamino acid- and sugar-conjugated peptides, and peptide purification and analysis.