1st Edition

Amino Acids: Insights and Roles in Heterocyclic Chemistry Volume 2: Hydantoins, Thiohydantoins, and 2,5-Diketopiperazines

By Zerong Wang Copyright 2023
    424 Pages 4 Color & 220 B/W Illustrations
    by Apple Academic Press

    424 Pages 4 Color & 220 B/W Illustrations
    by Apple Academic Press

    This is the second 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 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 α-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.

    In Volume 2: Hydantoins, Thiohydantoins, and 2,5-Diketopiperazines compiles the three IUPAC accepted nomenclature systems for heterocyclic compounds, which will be very useful for readers working in the heterocyclic chemistry field for giving 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. The other volumes include:

    Volume 1: Protecting Groups

    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. Heterocyclic Compounds

    Introduction to Heterocyclic Compounds • Summary of Literature Reviews on Heterocycles • General Nomenclature Rules on Heterocycles • Heterocyclic Compounds from a-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


    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).