Chemical Reagents for Protein Modification Fourth Edition Chemical Reagents for Protein Modification Fourth Edition Roger L. Lundblad Chapel Hill, North Carolina, USA CRC Press Taylor & Francis Group 6000 Broken Sound Parkway NW, Suite 300 Boca Raton, FL 33487-2742 © 2014 by Taylor & Francis Group, LLC CRC Press is an imprint of Taylor & Francis Group, an Informa business No claim to original U.S. Government works Version Date: 20131119 International Standard Book Number-13: 978-1-4665-7191-4 (eBook - PDF) This book contains information obtained from authentic and highly regarded sources. Reasonable efforts have been made to publish reliable data and information, but the author and publisher cannot assume responsibility for the valid- ity of all materials or the consequences of their use. 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Contents Preface...............................................................................................................................................ix Acknowledgments .............................................................................................................................xi Author ............................................................................................................................................ xiii Chapter 1 Introduction to the Chemical Modication of Proteins ...............................................1 References .................................................................................................................20 Chapter 2 Alkylating Agents ...................................................................................................... 35 References ..................................................................................................................96 Chapter 3 Acylating Agents ........................................................................................................97 References ................................................................................................................124 Chapter 4 Nitration and Nitrosylation ....................................................................................... 127 Nitration.................................................................................................................... 138 References ................................................................................................................ 148 Chapter 5 Oxidation .................................................................................................................. 161 References ............................................................................................................... 178 Chapter 6 Modication of Proteins with Reducing Agents ...................................................... 185 References ...............................................................................................................204 Chapter 7 Chemical Modication of Cysteine ......................................................................... 217 Alkyl Alkanethiosulfonates .....................................................................................283 References ...............................................................................................................307 Chapter 8 Chemical Modication of Cystine ........................................................................... 339 References ...............................................................................................................364 Chapter 9 Modication of Methionine ..................................................................................... 377 References ................................................................................................................ 389 Chapter 10 Modication of Carboxyl Groups in Proteins ..........................................................399 References ............................................................................................................... 421 vii viii Contents Chapter 11 Modication of Tyrosine Residues ........................................................................... 435 References ............................................................................................................... 474 Chapter 12 Modication of Tryptophan .....................................................................................489 References ............................................................................................................... 512 Chapter 13 Modication of Amino Groups ................................................................................ 523 References ...............................................................................................................563 Chapter 14 Modication of Histidine ......................................................................................... 581 References ............................................................................................................... 612 Chapter 15 Modication of Arginine .........................................................................................625 References ............................................................................................................... 653 Preface This is the fourth edition of a work rst published in 1983 in collaboration with Dr. Claudia Noyes. There have been two editions in the intervening years, which have provided a modest update. The current work has undergone major revision and has emerged far larger than when I started this work. I have tried to provide an even more encyclopedic coverage of a eld that is not nearly as popular as it was when the rst work appeared in 1983. On the other hand, times do change and chemical modication may again have the popularity of 40 years ago (see Chargaff, 1970). As with current editions, I continue to be embarrassed by what I missed in early work and apologize in advance to those investigators who I have yet again missed in the current work. As a word of caution, care must be taken with specicity. Mass spectrometry does provide a way of identifying modication, which, in the past, would have been silent. Finally, I cannot recall the source, perhaps Efraim Racker, who commented, “no reagent is as specic as when it is discovered.” REFERENCE Chargaff, E., Triviality in science: A brief meditation on fashions, Perspect. Biol. Med. Spring, 324–333, 1970. ix Acknowledgments I acknowledge the persistence of Barbara Norwitz in getting this work started and the help of Jill Jurgensen in turning a box of stuff into a useful volume. I also thank Professor Bryce Plapp of the University of Iowa for his continuing support of the thermodynamically challenged. xi Author Roger L. Lundblad is a native of San Francisco, California. He earned his undergraduate educa- tion at Pacic Lutheran University and his PhD in biochemistry from the University of Washington. After his postdoctoral work in the laboratories of Stanford Moore and William Stein at The Rockefeller University, he joined the faculty of the University of North Carolina at Chapel Hill. He then joined the Hyland Division of Baxter Healthcare in 1990. Currently, Dr. Lundblad works as an independent consultant at Chapel Hill, North Carolina, and writes on biotechnological issues. He is an adjunct professor of pathology at the University of North Carolina at Chapel Hill. xiii Introduction to the Chemical 1 Modification of Proteins This is the fourth edition of this work and, as with past editions, it is intended to provide a compre- hensive review of reagents used for the chemical modication of proteins. There is a considerable history of the chemical modication of proteins, which is largely beyond the scope of the present volume. There will be occasional mention of the older literature in the current work when necessary but the serious reader is directed to several excellent reviews.1–4