2nd Edition

Chemistry of Protein and Nucleic Acid Cross-Linking and Conjugation

By Shan S. Wong, David M. Jameson Copyright 2012
    622 Pages 3 Color & 198 B/W Illustrations
    by CRC Press

    Since the publication of the first edition of Chemistry of Protein Conjugation and Cross-Linking in 1991, new cross-linking reagents, notably multifunctional cross-linkers, have been developed and synthesized. The completion of the human genome project has opened a new area for studying nucleic acid and protein interactions using nucleic acid cross-linking reagents, and advances have also been made in the area of biosensors and microarray biochips for the detection and analysis of genes, proteins, and carbohydrates. In addition, developments in physical techniques with unprecedented sensitivity and resolution have facilitated the analysis of cross-linked products.

    Updated to reflect the advances of the 21st century, this book offers:

    • An overview of the chemical principles underlying the processes of cross-linking and conjugation
    • A thorough list of cross-linking reagents published in the literature since the first edition, covering monofunctional, homobifunctional, heterobifunctional, multifunctional, and zero-length cross-linkers
    • Reviews of the use of these reagents in studying protein tertiary structures, geometric arrangements of subunits within complex proteins and nucleic acids, near-neighbor analysis, protein-to-protein or ligand–receptor interactions, and conformational changes of biomolecules
    • Discusses the application of immunoconjugation for immunoassays, immunotoxins for targeted therapy, microarray technology for analysis of various biomolecules, and solid state chemistry for immobilizations

    Overview of Protein Conjugation
    References

    Review of Protein and Nucleic Acid Chemistry
    Introduction
    Protein Composition
    Protein Functional Groups
    Nucleic Acid Chemistry
    References

    Reagents Targeted to Specific Functional Groups
    Introduction.
    Sulfhydryl Reagents
    Amino Group–Specific Reagents
    Reagents Directed toward Carboxyl Groups
    Arginine-Specific Reagents.
    Histidine-Selective Reagents
    Methionine-Alkylating Reagents
    Tryptophan-Specific Reagents
    Serine-Modifying Reagents
    References

    How to Design and Choose Cross-Linking Reagents
    Introduction
    Use of Nucleophilic Reactions
    Use of Electrophilic Reactions
    Incorporating Group-Directed Reagents
    Incorporating Photoactivatable Nonspecific Groups
    Changing the Water Solubility of Cross-Linkers
    Incorporating Special Characteristics in the Bridge Spacer
    References

    Homobifunctional Cross-Linking Reagents
    Introduction
    Amino Group–Directed Cross-Linkers
    Sulfhydryl Group–Directed Cross-Linkers
    Carboxyl Group–Directed Cross-Linking Agents
    Phenolate and Imidazolyl Group–Directed Cross-Linking Reagents
    Arginine Residue–Directed Cross-Linkers
    Methionine Residue Cross-Linking Agent
    Carbohydrate Moiety–Specific Reagents
    Nondiscriminatory Photoactivatable Cross-linkers
    Noncovalent Homobifunctional Cross-Linking Reagents
    Nucleic Acid Cross-Linking Reagents
    References

    Heterobifunctional Cross-Linkers
    Introduction
    Group-Selective Heterobifunctional Reagents for Protein Cross- Linking
    Protein-Photosensitive Heterobifunctional Cross-Linking Reagents
    Noncovalent Immunoglobulin Cross-Linking System
    Heterobifunctional Nucleic Acid Cross-Linking Reagents
    References

    Multifunctional Cross-Linking Reagents
    Introduction
    Trifunctional Cross-Linkers
    Tetrafunctional Cross-Linkers
    Multifunctional Cross-Linkers
    Noncovalent Cross-Linkers
    References

    Monofunctional and Zero -Length Cross -Linking Reagents
    Introduction
    Monofunctional Cross-Linking Reagents
    Zero-Length Cross-Linking Reagents
    References

    General Approaches for Chemical Cross-Linking
    Introduction
    Classification of Cross-Linking Procedures
    General Conditions for Cross-Linking
    Cross-Linking Protocols for Commonly Used Reagents
    Cross-Linking Protocols Based on Biological Systems
    Conditions for Cleavage of Cross-Linked Complexes
    Reaction Complications
    References

    Analysis of Cross-Linked Products
    Introduction
    Techniques
    References

    Applications of Chemical Cross-Linking to the Study of Biological Macromolecules
    Introduction
    Determination of Tertiary Structures of Proteins
    Determination of Quaternary Structures of Proteins
    Determination of Protein–Protein Interactions
    Detection of Protein Conformational Changes
    Determination of Nucleic Acid Interaction and Nucleic Acid–Protein Interaction
    Effects of Cross-Linking on Structural Stability and Biological Activity
    References

    Applications of Chemical Conjugation in the Preparation of Immunoconjugates and Immunogens
    Introduction
    Preparation of Immunoconjugates
    Preparation of Immunogens
    Characterization of Conjugation Methods
    References

    Application of Chemical Conjugation for the Preparation of Immunotoxins and Other Drug Conjugates for Targeting Therapeutics
    Introduction
    Targeting Agents and Toxins
    Preparation of Therapeutic Conjugates
    References

    Application of Chemical Conjugation to Solid-State Chemistry
    Introduction
    Functionalities of Matrices
    Protein Immobilization by Matrix Activation
    Cross-Linking Reagents Commonly Used for Immobilization of Biomolecules
    Immobilization by Cross-Linking through Carbohydrate Chains
    Examples of Applications of Solid-Phase Immobilization Chemistry
    References

    Appendix A
    : Amino Group–Directed Homobifunctional Cross-Linkers
    Appendix B: Sulfhydryl Group– Directed Homobifunctional Cross-Linkers.
    Appendix C: Phenolate- and Imidazolyl-Group-Directed Reagents: Bisdiazonium Precursors
    Appendix D: Group Selective Heterobifunctional Cross-Linkers
    Appendix E: Photoactivatable Heterobifunctional Cross-Linking Reagents
    Index

    Biography

    Shan S. Wong, Ph.D., recently retired from the National Institutes of Health, where he served as a scientific review administrator and a program officer. In the latter capacity, he oversaw scientific programs in the area of alternative and complementary medicine. Previously, he served as director of clinical chemistry at Hermann Hospital and Lyndon B. Johnson General Hospital in Houston, Texas, and as a faculty member at the University of Texas Health Science Center at Houston. Before joining the University of Texas, Dr. Wong was a full professor of chemistry at the University of Massachusetts at Lowell. In addition to teaching at the University of Massachusetts at Lowell, he also taught chemistry courses at Denison University, Granville, Ohio, and Ohio State University, Columbus.

    Dr. Wong has published extensively in various scientific journals in the area of enzymology and clinical chemistry. He has received numerous honors and awards and has been active in various professional societies.

    David M. Jameson, Ph.D., joined the Department of Cell and Molecular Biology at the John A. Burns School of Medicine at the University of Hawaii in 1989, where he is presently a full professor. Before moving to Hawaii he was on the faculty of the Pharmacology Department at the University of Texas Southwestern Medical School in Dallas.

    Dr. Jameson received his BS in chemistry from Ohio State University in 1971 and his PhD in biochemistry from the University of Illinois at Urbana-Champaign in 1978. His thesis advisor was Gregorio Weber, who laid the foundations of modern fluorescence spectroscopy. Dr. Jameson carried out postdoctoral research at the Université Paris-Sud at Orsay, France before returning to the University of Illinois for a postdoctoral period in Gregorio Weber’s laboratory. In 1983, he joined the Pharmacology Department at the University of Texas Southwestern Medical Center at Dallas as an assistant professor. In 1989, he moved to the University of Hawaii.

    Dr. Jameson’s primary research focus has always been the development and application of fluorescence approaches for the study of biomolecular interactions, in particular protein–protein and protein–ligand interactions. He has published extensively in this area (some 130 publications to date) and has received funding from the National Science Foundation, the American Heart Association, and the National Institutes of Health. He has also received the Established Investigator Award from the American Heart Association and the 2004 Gregorio Weber Award for Excellence in Fluorescence Theory and Application. He lectures at numerous fluorescence workshops around the world and is co-organizer of the International Weber Symposium on Innovative Fluorescence Methodologies in Biochemistry and Medicine held every three years in Hawaii.