Biology

Amino Acids: Insights and Roles in Heterocyclic Chemistry, 4-volume set Zerong Wang, PhD Ordering Info/Buy Book

Published. Available now. Pub Date: May 2023 Hardback Price: see ordering info Hard ISBN: 9781774911501 E-Book ISBN: 9781003330196 Pages: 1672pp w index Binding Type:  Notes: 21 color and 996 b/w illustrations

This first-of-its-kind four-volume book series, Amino Acids: Insights and Roles in Heterocyclic Chemistry, provides readers with up-to-date information on alpha-amino acids, the potential challenges in working with alpha-amino acids, the protecting groups for the carboxyl, amino and side chain groups of the amino acids, and the most popular heterocyclic compounds that are originating from alpha-amino acids. These heterocyclic compounds include hydantoins, thiohydantoins (including 2-thiohydantoins, 4-thiohydantoins, 2,4-dithiohydantoins), 2,5-diketopiperazines, N-carboxyanhydrides, N-thiocarboxyanhydrides, sydnones, sydnonimines, azlactones, pseudoazlactones, and oxazolidin-5-ones. This is the first resource to comprehensively collect all the heterocycles that can be directly prepared from alpha-amino acids. In addition, almost all kinds of synthetic methods for a particular type of heterocycles from alpha-amino acids are included, along with the detailed mechanistic discussions and experimental procedures.

Volume 1: Protecting Groups collects and discusses the 260 protecting groups relating to amino acids, which have been organized by carboxyl group, amino group, and side chain groups. The conditions to introduce these protecting groups as well as their deprotecting procedures have also been incorporated, along with the physical properties, solvent effects, and temperature effects on the solubility of amino acids. It presents the solubility of glycine and phenylalanine in a variety of solvent systems to show the impact on amino acid, where glycine generally represents the polar amino acid whereas phenylalanine represents the amino acid of non-polar side chain.

In Volume 2: Hydantoins, Thiohydantoins, and 2,5-Diketopiperazines, the author has compiled the three IUPAC accepted nomenclature systems for heterocyclic compounds, which will be very useful for readers working in the heterocyclic chemistry field for giving the synthesized molecules their correct names. In addition, three groups of heterocyclic compounds, i.e., hydantoins, thiohydantoins (including 2-thiohydantoin, 4-thiohydantoin and 2,4-dithiohydantoin), and 2,5-diketopiperazines, have been organized with updated literature information. Particularly, all three groups of heterocyclic compounds have demonstrated many important biological activities, particularly anticancer and antibacterial activities. On the other hand, these three groups of heterocycles can be applied as substrates to make other chemical derivatives, particularly novel unnatural amino acids. All their reactivities have been compiled and updated. These will be very valuable for readers who have been working in this area or have interest in this area.

Volume 3: N-Carboxyanhydrides, N-Thiocarboxyanhydrides, Sydnones, and Sydnonimines presents up-to-date detailed information on two types of heterocyclic compounds that are originated from alpha-amino acids: NCAs/NTAs and sydnones/sydnonimines. The volume also covers the more than 10 initiating systems for the NCA monomers to undergo the ring-opening polymerization, which are very useful for readers in order to make living polypeptides/polypeptoids. In addition, the method to characterize these prepared polypeptides/polypeptoids are included. Particularly, two modern mass spectrometric techniques (MALDI-TOF and ESI-TOF) have been explained with detailed examples, where the elucidation of molecular weight of protein based on the ESI-TOF spectra have been given with a practical example as well as the theory that is based on, a unique feature of the volume.

Volume 4: Azlactones and Oxazolidin-5-ones discusses two types of simple heterocycles that can be prepared from alpha-amino acids, i.e., azlactones (also known as oxazolones, 4-unsaturated azlactones included) and oxazolidin-5-ones. These heterocyclic compounds behave differently in both biological and chemical properties, and their biological activities are presented in a well-organized manner in this volume.

This unique 4-volume set thoroughly covers more than seven types of heterocyclic compounds that are originated from alpha-amino acids, providing carefully compiled updated information with detailed examples. The author has shared many thoughtful insights based on his strong background in physical organic chemistry. The volumes will be highly valuable for graduate students and senior students, as well as for professors and researchers working in the field of medicinal and pharmaceutical chemistry, organic chemistry, organic synthesis, heterocycles, and proteins and peptides.

Click here for Volume 1: Protecting Groups
Click here for Volume 2: Hydantoins, Thiohydantoins, and 2,5-Diketopiperazines
Click here for Volume 3: N-Carboxyanhydrides, N-Thiocarboxyanhydrides, and Sydnones
Click here for Volume 4: Azlactones and Oxazolidin-5-ones

CONTENTS:
Volume 1: Protecting Groups

Preface

1. Introduction to Amino Acids
Introduction to Carboxylic Acids • Introduction to Aliphatic Amines • Introduction to General Amino Acids • The Common alpha-Amino Acids That Construct Proteins

2. The Dilemma of Working with alpha-Amino Acids
Impact of Solvent on the Solubility of alpha-Amino Acids • Temperature Effect on the Solubility of alpha-Amino Acids • Salting Effect and pH Effect on the Solubility of alpha-Amino Acids • Measures to Deal with Amino Acid Solubility

3. The Carboxyl Protecting Groups
Introduction to Carboxyl Protecting Groups • Alkyl Protecting Groups • alpha-Heteroatom Substituted Methyl Protecting Groups • b-Heteroatom Substituted Ethyl Protecting Group • Acetol Protecting Group • Unsaturated Protecting Groups • The Aryl Protecting Groups • Orthoester Protecting Groups • p-Azobenzenecarboxamidomethyl (OAbc) Protecting Group • Hydrazine Protecting Group • 5,6-Dihydrophenanthridine Protecting Group • Oxazoline, Oxazolidine, 5,6-Dihydro-1,3-oxazine and Boroxazolidone Protecting Groups • Transient or Temporary Protection of Carboxyl Group

4. Amino Protecting Groups
Introduction on Amino Protecting Groups • Acid-Labile Amino Protecting Groups • Alkali-Labile Amino Protecting Groups • Protecting Groups Removable by Hydrogenolysis • Thiolysis Cleavable Amino Protecting Group • Hydrazine Labile Amino Protecting Group

5. Side Chain Protecting Groups
Introduction • Hydroxyl Protecting Groups for Serine, Threonine, Tyrosine and Hydroxyproline • Amino Protecting Groups for Lysine • Protecting Groups for Arginine • Protecting Groups for Histidine • Protecting Groups for Asparagine and Glutamine • Protecting Groups for Aspartic Acid and Glutamic Acid • Protecting Groups for Cysteine and Selenocysteine • Protecting Groups for Tryptophan • Protecting Groups for Methionine

Subject Index
Index of Protecting Groups
Chemical Index
Inorganic Reagents Index

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Volume 2: Hydantoins, Thiohydantoins and 2,5-Diketopiperazines

Preface

1. Heterocyclic Compounds
Introduction to Heterocyclic Compounds • Summary of Literature Reviews on Heterocycles • General Nomenclature Rules on Heterocycles • Heterocyclic Compounds from alpha-Amino Acids

2. Hydantoin
Introduction • Structure • Natural Hydantoins • Preparative Methods • Reactions • Applications

3. Thiohydantoins
Introduction • Biological Activities • Preparative Methods • Reactions • Applications

4. 2,5-Diketopiperazine
Introduction • Natural Abundance • Biological Activities • Preparative Methods • Reactions of DKPs • Applications

Index

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Volume 3: N-Carboxyanhydrides, N-Thiocarboxyanhydrides, Sydnones, and Sydnonimines

Preface

1. alpha-Amino Acid N-Carboxyanhydrides (NCA) and N-Thiocarboxyanhydrides (NTA)
Introduction • Preparative Methods • Polymerization of N-Carboxyanhydrides • Polymerization of N-Thiocarboxyanhydrides • Characterization of Polypeptides

2. Sydnones and Sydnonimines
Introduction of Sydnone • Biological Activities of Sydnones • Preparative Methods of Sydnones • Reactions of Sydnones • Sydnone Imines

Index

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Volume 4: Azlactones and Oxazolidin-5-ones

Preface

1. Azlactones
Introduction • Biological Activities • Preparative Methods • Reactions • Applications • Pseudoazlactones • Final Comments

2. Oxazolidin-5-Ones
Introduction • Natural Occurrence • Biological Activities • Preparative Methods • Reactions of Oxazolidin-5-ones • Application

Index

About the Authors / Editors:
Zerong Wang, PhD
Professor of Chemistry, College of Science and Engineering, University of Houston-Clear Lake, Texas

Zerong Wang, PhD, is a full Professor at the University of Houston-Clear Lake, Texas. Prior to that, he worked at the Institute for Biological Sciences of the National Research Council of Canada for several years. Through his career, the author has gained specific training and expertise in organic chemistry, particularly in physical organic chemistry and other subdisciplines that include photochemistry, spectroscopies, carbohydrate chemistry, sulfur chemistry, nucleosides and heterocycles, material science, reaction methodology, computational chemistry, among others. Dr. Wang has developed research projects relating to sulfur chemistry, computational chemistry, nucleoside analogs, heterocycle chemistry, materials science, and macromolecules (pillarene, calix[n]arene, and melamine-based dendrimers, etc.) and has received 22 research grants, including from NSF-MRI, NSF-STEM, Welch Research Grant, Welch Departmental Research Grant, and University of Houston-Clear Lake’s Faculty Research and Support Fund (FRSF) Grants.

The author has developed two compendiums in organic chemistry: Comprehensive Organic Named Reactions, with Detailed Mechanism Discussions and Updated Experimental Procedures (3 volumes) (Wiley, 2009) and Encyclopedia of Physical Organic Chemistry (6 volumes) (Wiley, 2017), the PROSE Award winner in 2018.

While conducting research activities, the author also teaches courses for both graduate and undergraduate students. To date, the author has taught courses on General Chemistry, General Chemistry Laboratory, Analytical Chemistry, Quantitative Chemical Analysis, Forensic Chemistry, Organic Chemistry, Organic Chemistry Laboratory, Advanced Organic Chemistry, Physical Organic Chemistry, Synthetic Organic Chemistry, Organometallic Chemistry, Biochemistry, Biochemistry Laboratory, Polymer Chemistry, Introduction to Chemical Engineering, Nutrition and Diet Chemistry, Green Chemistry, Introduction to NMR Spectroscopy, Chemistry Seminar, Graduate Research, and Chemistry for nonscience majors.

Dr. Wang earned his BS degree in Chemistry from Lanzhou University, PR China, and earned his MS and PhD degrees from the Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences. He conducted his postdoctoral research at the Department of Chemistry, University of California Berkeley and York University (Canada).

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