Chemistry Of Peptide Synthesis - N Benoiton (2006) Ww, ebooki

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//-->CHEMISTRYOFPEPTIDESYNTHESISN. Leo BenoitonUniversity of OttawaOttawa, Ontario, CanadaBoca Raton London New York SingaporeA CRC title, part of the Taylor & Francis imprint, a member of theTaylor & Francis Group, the academic division of T&F Informa plc.© 2006 by Taylor & Francis Group, LLCPublished in 2006 byCRC PressTaylor & Francis Group6000 Broken Sound Parkway NW, Suite 300Boca Raton, FL 33487-2742© 2006 by Taylor & Francis Group, LLCCRC Press is an imprint of Taylor & Francis GroupNo claim to original U.S. Government worksPrinted in the United States of America on acid-free paper10 9 8 7 6 5 4 3 2 1International Standard Book Number-10: 1-57444-454-9 (Hardcover)International Standard Book Number-13: 978-1-57444-454-4 (Hardcover)Library of Congress Card Number 2005005753This book contains information obtained from authentic and highly regarded sources. Reprinted material isquoted with permission, and sources are indicated. A wide variety of references are listed. Reasonable effortshave been made to publish reliable data and information, but the author and the publisher cannot assumeresponsibility for the validity of all materials or for the consequences of their use.No part of this book may be reprinted, reproduced, transmitted, or utilized in any form by any electronic,mechanical, or other means, now known or hereafter invented, including photocopying, microfilming, andrecording, or in any information storage or retrieval system, without written permission from the publishers.For permission to photocopy or use material electronically from this work, please accesswww.copyright.comDanvers, MA 01923, 978-750-8400. CCC is a not-for-profit organization that provides licenses and registrationfor a variety of users. For organizations that have been granted a photocopy license by the CCC, a separatesystem of payment has been arranged.Trademark Notice:Product or corporate names may be trademarks or registered trademarks, and are used onlyfor identification and explanation without intent to infringe.Library of Congress Cataloging-in-Publication DataBenoiton, N. Leo.Chemistry of peptide synthesis / N. Leo Benoiton.p. ; cm.Includes bibliographical references.ISBN-13: 978-1-57444-454-4 (hardcover : alk. paper)ISBN-10: 1-57444-454-9 (hardcover : alk. paper)1. Peptides--Synthesis.[DNLM: 1. Peptide Biosynthesis. QU 68 B456c 2005] I. Title.QP552.P4B46 2005612'.015756--dc222005005753Visit the Taylor & Francis Web site atTaylor & Francis Groupis the Academic Division of T&F Informa plc.and the CRC Press Web site at© 2006 by Taylor & Francis Group, LLCDedicationThis book is dedicated to Rao Makineni, a unique memberand benefactor of the peptide community.© 2006 by Taylor & Francis Group, LLCPrefaceThis book has emerged from courses that I taught to biochemistry students at theundergraduate and graduate levels, to persons with a limited knowledge of organicchemistry, to chemists with experience in other ﬁelds, and to peptide chemists. Itassumes that the reader possesses a minimum knowledge of organic and amino-acidchemistry. It comprises 188 self-standing sections that include 207 ﬁgures writtenin clear language, with limited use of abbreviations. The focus is on understandinghow and why reactions and phenomena occur. There are a few tables of illustrativedata, but no tables of compounds or reaction conditions. The material is presentedprogressively, with some repetition, and then with ampliﬁcation after the basics havebeen dealt with. The fundamentals of peptide synthesis, with an emphasis on theintermediates that are encountered in aminolysis reactions, are presented initially.The coupling of Nα-protected amino acids and Nα-protected peptides and theirtendencies to isomerize are then addressed separately. This allows for easier com-prehension of the issues of stereomutation and the applicability of coupling reactions.Protection of functional groups is introduced on the basis of the methods that areemployed for removal of the protectors. A chapter is devoted to the question ofstereomutation, which is now more complex, following the discovery that Nα-protected amino acids can also give rise to oxazolones. Other chapters are devotedto solid-phase synthesis, side-chain protection and side reactions, ampliﬁcation oncoupling methods, and miscellaneous topics. Points to note are that esters thatundergo aminolysis are referred to as activated esters, which is why they react, andnot active esters, and that in two cases two abbreviations (Z and Cbz; HOObt andHODhbt) are used haphazardly for one entity because that is the reality of the peptideliterature. An effort has been made to convey to the reader a notion of how the ﬁeldof peptide chemistry has developed. To this end, the references are located at theend of each section and include the titles of articles. Most references have beenselected on the basis of the main theme that the chapter addresses. When therelevance of a paper is not obvious from the title, a phrase has been inserted inparentheses. The titles of papers written in German and French have been translated.For obvious reasons the number of references had to be limited. I extend myapologies to anyone who considers his or her work to have been unjustiﬁably omitted.Some poetic license was exercised in the creation of the manuscript and the reactionschemes. Inclusion of all details and exceptions to statements would have made thewhole too unruly.I am greatly indebted to Dr. Brian Ridge of the School of Chemical and Bio-logical Sciences of the University of Exeter, United Kingdom, for his critical reviewof the manuscript and for his suggestions that have been incorporated into themanuscript. I solely am responsible for the book’s contents. I thank Professor JohnCoggins of the University of Glasgow for providing the references for Appendix 3,© 2006 by Taylor & Francis Group, LLC [ Pobierz całość w formacie PDF ]

Chemistry Of Peptide Synthesis - N Benoiton (2006) Ww, ebooki

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