In one place, all the heterocycles from ?-amino acids and the synthetic methods, with detailed mechanistic discussions and experimental procedures. It provides up-to-date information on the challenges in working with ?-amino acids, the protecting groups for the carboxyl, amino and side chain groups, and popular heterocyclic compounds.
Volume 1: Protecting Groups
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
Volume 2: Hydantoins, Thiohydantoins and 2,5-Diketopiperazines
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
Volume 3: N-Carboxyanhydrides, N-Thiocarboxyanhydrides, and Sydnones
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
Volume 4: Azlactones and Oxazolidin-5-ones
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
Biography
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).
