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This work provides a comprehensive overview of, and the most common and useful methods for, the synthesis of non-alpha-amino acids, particularly amino acids that are key synthetic intermediates or important compounds in their own right. Attention is paid to acyclic amino acids C3-C10 including amino alkanoic carboxylic acids, aminoalkenoic acids and aminoalkynoic acids.
By combining the tools of organic chemistry with those of physical biochemistry and cell biology, Non-Natural Amino Acids aims to provide fundamental insights into how proteins work within the context of complex biological systems of biomedical interest. The critically acclaimed laboratory standard for 40 years, Methods in Enzymology is one of the most highly respected publications in the field of biochemistry. Since 1955, each volume has been eagerly awaited, frequently consulted, and praised by researchers and reviewers alike. With more than 400 volumes published, each Methods in Enzymology volume presents material that is relevant in today's labs -- truly an essential publication for researchers in all fields of life sciences. - Demonstrates how the tools and principles of chemistry combined with the molecules and processes of living cells can be combined to create molecules with new properties and functions found neither in nature nor in the test tube - Presents new insights into the molecular mechanisms of complex biological and chemical systems that can be gained by studying the structure and function of non-natural molecules - Provides a "one-stop shop" for tried and tested essential techniques, eliminating the need to wade through untested or unreliable methods
Although less common than α-amino acids, non-α-amino acids—where the amino group is not on the carbon immediately adjacent to the carboxyl group but is attached to another carbon in the chain (for example, the β, γ, δ carbon)—are components of biologically important molecules, are significant in the pharmaceutical industry, and are useful starting materials for many areas of organic chemistry. Since the publication of the first edition of this book nearly 20 years ago, synthetic work devoted to the preparation of non- α-amino acids has expanded greatly. Methods of Non-α-Amino Acid Synthesis, Second Edition has been extensively rewritten and reorganized, providing an up-to-date review of strategies and methods for non-α-amino acid synthesis, particularly those amino acids that are key synthetic intermediates or important compounds in their own right. It focuses on acyclic amino acids of C3–C10, but also aminoalkanoic carboxylic acids, aminoalkenoic acids, and aminoalkynoic acids. The new edition contains many updated references and has a greater emphasis on the biological importance of non-α-amino acids. In addition to an array of synthetic methods, the book offers discussions on why non-α-amino acids are important. The book covers synthetic methods that rely on substituent refunctionalization, the conversion of cyclic precursors to acyclic amino acids, conjugate addition reactions, and enolate anion reactions and condensation reactions that lead to non-α-amino acids. It also examines reactions and strategies that lead to good diastereoselectivity and enantioselectivity during synthesis. A chapter devoted to biologically important amino acids includes separate sections on GABA, GABOB, carnitine, DAVA, statine, and other significant amino acids as well as a new section on peptides and proteins that contain non-α-amino acids. The final chapter addresses aminocyclic and heterocyclic amino acids.
Even though they are present in nature, non-proteinogenic amino acids are usually defined as unnatural or non-natural. Beside their structural diversity, interest in these compounds is due to their occurrence in nature, their biological properties, the analytical aspects, their use as probes, and their incorporation into peptides and proteins, among other reasons. Divided into five convenient sections, Unnatural Amino Acids: Methods and Protocols deals with enzymatic methods used to produce non-natural amino acids, aspects concerning the presence of unnatural amino acids in peptides with antimicrobial properties, genetic incorporation of unnatural amino acids into proteins (yeast and mammalian cells), and detection and quantification of D-amino acids and related enzymes. Written in the highly successful Methods in Molecular BiologyTM series format, chapters contain introductions to their respective topics, lists of the necessary materials and reagents, step-by-step, readily reproducible laboratory protocols, and notes on troubleshooting and avoiding known pitfalls. Authoritative and accessible, Unnatural Amino Acids: Methods and Protocols serves as an ideal guide for scientists and contributes to directing the attention of researchers to the many fields of growing scientific interest in non-natural amino acids.
Containing all the new as well as classical methodologies used in the investigation of amino acid and protein metabolism in human and animal models, this book is needed because of the dramatic increase in research in this field. There is no other book currently on the market that covers these methods of investigation. Methods for Investigation of Amino Acid and Protein Metabolism explores areas such as amino acid transfer across tissue membranes, past and new applications using stable isotopes, protein synthesis in organs and tissues, and more. Because of the importance of research methods in the field of amino acid and protein nutrition and metabolism, this book facilitates the reader's integration of the concepts involved in these investigative research methods and their corollaries. In addition to helping any nutrition investigator design and conduct appropriate research protocols in this area of nutrition, this book assists students who are planning to investigate amino acid and protein metabolism in humans or laboratory animals.
In recent years, organo-fluorine chemistry has made a marked impact on the design and synthesis of a large variety of biologically active molecules, such as steroids, carbohydrates, amines, amino acids, peptides and other natural products. Naturally occurring amino acids play a pivotal role in living systems, and therefore synthetic fluorine-containing amino acids have been of significant interest to researchers working towards the understanding and modification of physiological processes. Fluorine-containing Amino Acids: is the first volume devoted to the synthesis and properties of fluorine-containing amino acids pays special attention to the preparation of enantiomerically pure acids (which are essential to the modern pharmaceutical industry) deals with a rapidly expanding field of research has been written by experienced researchers who are responsible for many developments in the field highlights the interdisciplinary nature of this topic Fluorine-containing Amino Acids is the only dedicated reference in this subject and will be essential for researchers in synthetic organic, peptide, natural product, and medicinal chemistry and biochemistry.
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.
Introduction what is organic chemistry all about?; Structural organic chemistry the shapes of molecules functional groups; Organic nomenclature; Alkanes; Stereoisomerism of organic molecules; Bonding in organic molecules atomic-orbital models; More on nomenclature compounds other than hydrocarbons; Nucleophilic substitution and elimination reactions; Separation and purification identification of organic compounds by spectroscopic techniques; Alkenes and alkynes. Ionic and radical addition reactions; Alkenes and alkynes; Oxidation and reduction reactions; Acidity or alkynes.