1st Edition

Amino Acids: Insights and Roles in Heterocyclic Chemistry Volume 1: Protecting Groups

By Zerong Wang Copyright 2023
    432 Pages 2 Color & 341 B/W Illustrations
    by Apple Academic Press

    432 Pages 2 Color & 341 B/W Illustrations
    by Apple Academic Press

    This is the first volume of a first-of-its-kind four-volume book set that provides readers with up-to-date information on α-amino acids, the potential challenges in working with α-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 α-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 α-amino acids. In addition, almost all kinds of synthetic methods for a particular type of heterocycles from α-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 group. 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.

    The other volumes include:

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

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

    Volume 4: Azlactones and Oxazolidin-5-ones

    All together, this unique 4-volume set thoroughly covers the two 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.

    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


    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 other. 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 Non-Science 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).