Solid-phase Synthesis of Peptides and Peptide Mimetics Using Urethane and Backbone Amide Linker Strategies PDF Download
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Author: Ramakrishna Sasubilli Publisher: ISBN: Category : Languages : en Pages : 148
Book Description
Peptide-based agents are of considerable interest as bioactive agents and drugs. Research was done to synthesize peptides and peptides mimetics using classical solid-phase peptide synthesis (SPPS) in the C-to-N direction. However, this strategy is not generally useful for preparing C-terminally modified peptide derivatives. On the other hand, SPPS in the N-to-C direction (inverse SPPS) would provide the synthetically versatile C-terminal carboxyl group for further elaboration. The first objective of this project was to develop inverse SPPS based urethane attachment strategy. Research was done to develop this strategy on hydroxymethyl polystyrene resin. In order to demonstrate this strategy, several C-terminal peptide mimetics, including peptide boronic acids, peptide hydroxamic acids, and peptide trifluoromethylketones were synthesized. The second objective was to develop the backbone amide linker (BAL) attachment strategy. This strategy provides a potential bidirectional approach to synthesize peptides and peptide mimetics. BAL strategy has been developed using a 4-(4-formyl-3-methoxyphenoxy)butyryl resin.
Author: Ramakrishna Sasubilli Publisher: ISBN: Category : Languages : en Pages : 148
Book Description
Peptide-based agents are of considerable interest as bioactive agents and drugs. Research was done to synthesize peptides and peptides mimetics using classical solid-phase peptide synthesis (SPPS) in the C-to-N direction. However, this strategy is not generally useful for preparing C-terminally modified peptide derivatives. On the other hand, SPPS in the N-to-C direction (inverse SPPS) would provide the synthetically versatile C-terminal carboxyl group for further elaboration. The first objective of this project was to develop inverse SPPS based urethane attachment strategy. Research was done to develop this strategy on hydroxymethyl polystyrene resin. In order to demonstrate this strategy, several C-terminal peptide mimetics, including peptide boronic acids, peptide hydroxamic acids, and peptide trifluoromethylketones were synthesized. The second objective was to develop the backbone amide linker (BAL) attachment strategy. This strategy provides a potential bidirectional approach to synthesize peptides and peptide mimetics. BAL strategy has been developed using a 4-(4-formyl-3-methoxyphenoxy)butyryl resin.
Author: W. Chan Publisher: Oxford University Press ISBN: 019156589X Category : Science Languages : en Pages : 371
Book Description
In the years since the publication of Atherton and Sheppard's volume, the technique of Fmoc solid-phase peptide synthesis has matured considerably and is now the standard approach for the routine production of peptides. The basic problems at the time of publication of this earlier work have now for the most part, been solved. As a result, innovators in the field have focussed their efforts to develop methodologies and chemistry for the synthesis of more complex structures. The focus of this new volume is much broader, and covers the essential procedures for the production of linear peptides and more advanced techniques for preparing cyclic, side-chain modified, phospho- and glycopeptides. Many other methods also deserving attention have been included: convergent peptide synthesis; peptide-protein conjugation; chemoselective ligation; and chemoselective purification. The difficult preparation of cysteine and methionine-containing peptides is also covered, as well as methods for overcoming aggregation during peptide chain assembly. Many of the techniques developed for the production of large arrays of peptides by parallel synthesis, such as t-bag, SPOT and PIN synthesis, have naturally been included. Finally, a survey of available automated instrumentation has also been provided.
Author: Fernando Albericio Publisher: CRC Press ISBN: 9780824703592 Category : Science Languages : en Pages : 852
Book Description
This volume provides the information needed to synthesize peptides by solid-phase synthesis (SPS) - employing polymeric support (resins), anchoring linkages (handles), coupling reagents (activators), and protection schemes. It presents strategies for creating a wide variety of compounds for drug discovery and analyzes peptides, DNA, carbohydrates, conjugates of biomolecules, and small molecules.
Author: Paul Lloyd-Williams Publisher: CRC Press ISBN: 1000151689 Category : Cooking Languages : en Pages : 306
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.
Author: Gregg B. Fields Publisher: Academic Press ISBN: Category : Medical Languages : en Pages : 828
Book Description
The critically acclaimed laboratory standard for more than forty years, Methods in Enzymology is one of the most highly respected publications in the field of biochemistry. Since 1955, each volumehas been eagerly awaited, frequently consulted, and praised by researchers and reviewers alike. More than 275 volumes have been published (all of them still in print) and much of the material is relevant even today-truly an essential publication for researchers in all fields of life sciences. Key Features * Solid-phase peptide synthesis * Applications of peptides for structural and biological studies * Characterization of synthetic peptides
Author: Erhard Gross Publisher: Elsevier ISBN: 1483217965 Category : Science Languages : en Pages : 454
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.
Author: John Howl Publisher: Springer Science & Business Media ISBN: 1592598773 Category : Science Languages : en Pages : 263
Book Description
Hands-on experts describe in step-by-step detail the key methodologies of contemporary peptide synthesis and illustrate their numerous applications. The techniques presented include protocols for chemical ligation, the synthesis of cyclic and phosphotyrosine-containing peptides, lipoamino acid- and sugar-conjugated peptides, and peptide purification and analyses. Additional chapters detail methodologies and instrumentation for high-throughput peptide synthesis, many different applications of peptides as novel research tools and biological probes, and the design and application of fluorescent substrate-based peptides that can be used to determine the selectivity and activity of peptidases. A practical guide to the identification of proteins using mass spectrometric analyses of peptide mixtures is also included.
Author: Gregory Grant Publisher: Oxford University Press ISBN: 9780198030430 Category : Science Languages : en Pages : 404
Book Description
The first synthetic peptides were produced a century ago. In the ensuing period, they have developed as valuable research tools that are readily available to all researchers. However, since most researchers 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 the second edition of a volume that was first published 10 years ago. It is written by experts in the field who provide detailed descriptions as well as practical advice for producing and using synthetic peptides. The various chapters cover peptide design considerations, the synthetic chemistry, the evaluation of the synthetic product, and the modern applications of synthetic peptides. This includes the basic principles of peptide structure, analysis and chain assembly as well as the latest in selective disulfide bond formation, new strategies for the production of large peptides, and sequencing peptides by mass spectrometry. This book was designed with the intent of providing useful information both for the novices to the field as well as more seasoned practitioners. Its contents will help prevent problems commonly encountered and allow scientists to optimize their use of synthetic peptides.
Author: Yi Yang Publisher: Academic Press ISBN: 0128011815 Category : Science Languages : en Pages : 378
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
Author: Ramakrishna Sasubilli
Author: Ramakrishna Sasubilli
Author: W. Chan
Author: Fernando Albericio
Author: Paul Lloyd-Williams
Author: Gregg B. Fields
Author: Erhard Gross
Author: John Howl
Author: Gregory Grant
Author: Yi Yang
Author: Roger Epton