Asymmetric Synthesis of Non-Proteinogenic Amino Acids
Asymmetric Synthesis of Non-Proteinogenic Amino Acids

Author: Ashot S. Saghyan

Publisher: John Wiley & Sons

Published: 2016-11-14

Total Pages: 376

ISBN-13: 3527340416

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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.

Synthesis of Optically Active Alpha-Amino Acids
Synthesis of Optically Active Alpha-Amino Acids

Author: R. M. Williams

Publisher: Elsevier

Published: 2013-10-22

Total Pages: 429

ISBN-13: 1483292959

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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.

Synthesis of Optically Active [alpha]-amino Acids
Synthesis of Optically Active [alpha]-amino Acids

Author: Robert Michael Williams

Publisher: Pergamon

Published: 1989

Total Pages: 436

ISBN-13:

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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.

Organo-catalytic Strategies Towards Alpha, Alpha - Disubstituted Amino Acid Derivatives
Organo-catalytic Strategies Towards Alpha, Alpha - Disubstituted Amino Acid Derivatives

Author: Henning Vogt

Publisher:

Published: 2006

Total Pages: 195

ISBN-13: 9783832513825

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The class of non-proteinogenic a,a u2011disubstituted amino acids and their derivatives is of high interest to biochemical and pharmacological research. This predicates on their ability to alter certain chemical and physicochemical properties of peptides and related structures. Moreover, the close structural relatedness to biologically relevant endogenous amino acid derivatives qualifies them in many cases to act as enzyme inhibitors or receptor antagonists.In the present study, the development of new strategies towards the synthesis of N u2011protected a,a u2011disubstituted amino aldehydes and their derivatives is demonstrated. Starting from ketones, a,a u2011disubstituted aldehydes were prepared in two or three steps. These aldehydes were subjected to stereoselective organo-catalysed a u2011amination reactions. The transfer of a procedure known for the a u2011amination of a u2011unbranched aldehydes with azodicarboxylates to racemic a u2011branched aldehydes delivered N u2011protected aminoaldehydes in up to 87 % yield and 86 % ee. The conversion of the amination products to the corresponding N u2011protected 4,4 u2011disubstituted oxazolidinones was accomplished, after in situ-reduction, in two additional steps.In addition to this method, a new strategy was devised using sulfonyl azides as aminating agent to deliver a u2011sulfamidated a,a u2011disubstituted aldehydes in up to 55 % yield and 86 % ee. A mechanism was proposed, which differs fundamentally from the mechanistic model usually ascribed to enamine catalysis. The transformation of the sulfamidation product into the free amino acid was accomplished in two steps.Since the two concepts follow different mechanistic routes, different enantiomers of N u2011protected, a,a u2011disubstituted aminoaldehydes are accessible by one catalyst. All reactions involved in the latter approach are free of transition metals. Therefore, the presented strategy could prove to be especially useful for medicinal chemistry.