Dynamic Combinatorial Chemistry: In Drug Discovery, Bioorganic Chemistry, And Materials Science

Dynamic Combinatorial Chemistry Dynamic Combinatorial Chemistry In Drug Discovery, Bioorganic Chemistry, and Materials Science Edited by Benjamin L. Miller University of Rochester Rochester, New York Copyright © 2010 by John Wiley & Sons, Inc. Published by John Wiley & Sons, Inc., Hoboken, New Jersey. All rights reserved. Published simultaneously in Canada No part of this publication may be reproduced, stored in a retrieval system, or transmitted in any form or by any means, electronic, mechanical, photocopying, recording, scanning, or otherwise, except as permitted under Section 107 or 108 of the 1976 United States Copyright Act, without either the prior written permission of the Publisher, or authorization through payment of the appropriate per-copy fee to the Copyright Clearance Center, Inc., 222 Rosewood Drive, Danvers, MA 01923, (978) 750-8400, fax (978) 750-4470, or on the web at www.copyright.com. Requests to the Publisher for permission should be addressed to the Permissions Department, John Wiley & Sons, Inc., 111 River Street, Hoboken, NJ 07030, (201) 748-6011, fax (201) 748-6008, or online at http://www.wiley.com/go/permission. Limit of Liability/Disclaimer of Warranty: While the publisher and author have used their best efforts in preparing this book, they make no representations or warranties with respect to the accuracy or completeness of the contents of this book and specifically disclaim any implied warranties of merchantability or fitness for a particular purpose. No warranty may be created or extended by sales representatives or written sales materials. The advice and strategies contained herein may not be suitable for your situation. You should consult with a professional where appropriate. Neither the publisher nor author shall be liable for any loss of profit or any other commercial damages, including but not limited to special, incidental, consequential, or other damages. For general information on our other products and services or for technical support, please contact our Customer Care Department within the United States at (800) 762-2974, outside the United States at (317) 572-3993 or fax (317) 572-4002. Wiley also publishes its books in a variety of electronic formats. Some content that appears in print may not be available in electronic formats. For more information about Wiley products, visit our web site at www.wiley.com. Library of Congress Cataloging-in-Publication Data: Miller, Benjamin L. Dynamic combinatorial chemistry : in drug discovery, bioorganic chemistry, and materials science / Benjamin L. Miller. p. cm. Includes index. ISBN 978-0-470-09603-1 (cloth) 1. Combinatorial chemistry. I. Title. QD262.M64 2009 615.19—dc22 2009019344 Printed in the United States of America 10 9 8 7 6 5 4 3 2 1 Contents Preface vii Contributors ix Chapter 1: Dynamic Combinatorial Chemistry: An Introduction 1 Benjamin L. Miller Chapter 2: Protein-Directed Dynamic Combinatorial Chemistry 43 Michael F. Greaney and Venugopal T. Bhat Chapter 3: Nucleic Acid-Targeted Dynamic Combinatorial Chemistry 83 Peter C. Gareiss and Benjamin L. Miller Chapter 4: Complex Self-Sorting Systems 118 Soumyadip Ghosh and Lyle Isaacs Chapter 5: Chiral Selection in DCC 155 Jennifer J. Becker and Michel R. Gagné Chapter 6: Dynamic Combinatorial Resolution 169 Marcus Angelin, Rikard Larsson, Pornrapee Vongvilai, Morakot Sakulsombat, and Olof Ramström v vi CONTENTS Chapter 7: Dynamic Combinatorial Chemistry and Mass Spectrometry: A Combined Strategy for High Performance Lead Discovery 201 Sally-Ann Poulsen and Hoan Vu Chapt