Authored by two internationally recognized experts with an excellent track record, this much-needed reference summarizes latest research in the rapidly developing field of stereoselective synthesis of enantiomerically enriched amino acids, particularly of non-proteinogenic origin. It highlights several different catalytic and stoichiometric asymmetric methods for their synthesis and also provides information on origin, biological properties, different synthetic strategies and important applications in medicine and pharmacology. Essential reading for synthetic chemists working in the field of asymmetric synthesis, natural products and peptide synthesis, stereochemistry, medicinal chemistry, biochemistry, pharmacology, and biotechnology.
Authored by two internationally recognized experts with an excellent track record, this much-needed reference summarizes latest research in the rapidly developing field of stereoselective synthesis of enantiomerically enriched amino acids, particularly of non-proteinogenic origin. It highlights several different catalytic and stoichiometric asymmetric methods for their synthesis and also provides information on origin, biological properties, different synthetic strategies and important applications in medicine and pharmacology. Essential reading for synthetic chemists working in the field of asymmetric synthesis, natural products and peptide synthesis, stereochemistry, medicinal chemistry, biochemistry, pharmacology, and biotechnology.
Asymmetric Synthesis of Natural Products Fully updated learning resource covering the concept of using natural product chemistry for strategies in asymmetric synthesis The third edition of Asymmetric Synthesis of Natural Products introduces students to the rapidly growing field of natural products in organic chemistry, discussing the practical, mainly pharmacological, importance of selected compounds and emphasizing the target-oriented approach of organic synthesis which is key in industrial strategies. To aid in reader comprehension, the text includes key references and an Index of Compounds. The textbook is based on two lecture courses (Asymmetric Synthesis & Asymmetric Synthesis of Natural Products), which the author has delivered more than 50 times over the past 20 years in Finland, the UK, Italy, and Greece. This third edition is fully updated from the earlier versions (published by Wiley in 1993 and 2012). The importance of natural products as truly renewable raw materials in sustainable chemistry and circular economy is illustrated through applications of e.g. organocatalysis, organometallic catalysis, and biocatalysis. The contents consist of traditional text supplemented with illustrations (such as chemical drawings and structural formulae). Three dimensional aspects are also discussed with the use of 3D renderings of structures for both reaction mechanisms (molecular modeling) and crystallographic data. Sample topics covered in the textbook include: The foundations of asymmetric synthesis, including the theory and applications of individual asymmetric reactions Sustainable development, the circular economy, and use of renewable raw materials that have become prominent in many fields of science and technology Various natural product classes, including carbohydrates, amino acids, peptides, proteins, nucleosides, nucleotides, nucleic acids, and polyketides The properties of these natural product classes, including their structures, biosynthesis, and interrelationships, as well as examples of asymmetric syntheses and the practical value of these compounds Asymmetric Synthesis of Natural Products is a comprehensive, authoritative, and up-to-date learning resource on the subject for advanced level undergraduate or early-stage graduate students. It is also useful for specialists already working in synthesis who wish to learn about asymmetric synthesis.
Non-proteinogenic amino acids are often important constituents of biologically potent natural products. The synthesis of these amino acids is often time-consuming, non-trivial and not sustainable. Thus, the central topic of this work was the formation of unusual amino acid structures by biocatalytic and catalytic methods. For the elucidation of the biosynthetic pathway of Streptomyces-produced muraymycins and related natural products, a ‘biosynthetic tool kit’ was compiled and prepared. This does not only comprehend the completed synthesis of deuterium-labeled compounds, such as (3R)- and (3S)-3-hydroxy-[5-2H]-l-arginine and other potential intermediates with a nucleosidic structure, but it also includes the development of fermentation methodology including the possibility to detect the muraymycin derivatives by LC MS. Furthermore, different synthetic routes with catalytic key steps for the preparation of the non-proteinogenic amino acid enduracididine were investigated.
The purpose of this book is to review and critically evaluate the best new methods to synthesize alpha-amino acids in optically active form. There is so much new literature on amino acid synthesis that the experimentalist will undoubtedly have difficulty in selecting the most appropriate methodology for constructing the amino acid of immediate interest. This book is a guide for steering the scientist through the maze of existing reports on the subject and contains the most up-to-date critical reviews of methods of asymmetric synthesis of amino acids. In areas that are relatively new conceptually and less studied experimentally, an effort has been made to review the most salient works with an eye towards future development. Over 330 schemes and figures are presented with references for rapid visual retrieval of information. The book will be of great value to academic and industrial organic research chemists, especially those concerned with medicinal and agricultural chemistry, as well as to graduate and post graduate students, biochemists and biologists.
