Incorporation of Heterocycles into Combinatorial Chemistry
The author has summarized a decade of teaching combinatorial chemistry into this timely brief. The solid phase synthesis of unnatural heterocyclic alpha-amino acids is illustrated by practical examples starting from the ABCs of peptide synthesis explored
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Eugene V. Babaev
Incorporation of Heterocycles into Combinatorial Chemistry 123
SpringerBriefs in Molecular Science
More information about this series at http://www.springer.com/series/8898
Eugene V. Babaev
Incorporation of Heterocycles into Combinatorial Chemistry
123
Eugene V. Babaev Chemistry Department Moscow State University Moscow Russia
ISSN 2191-5407 ISSN 2191-5415 (electronic) SpringerBriefs in Molecular Science ISBN 978-3-319-50013-3 ISBN 978-3-319-50015-7 (eBook) DOI 10.1007/978-3-319-50015-7 Library of Congress Control Number: 2016959806 © The Author(s) 2017 This work is subject to copyright. All rights are reserved by the Publisher, whether the whole or part of the material is concerned, specifically the rights of translation, reprinting, reuse of illustrations, recitation, broadcasting, reproduction on microfilms or in any other physical way, and transmission or information storage and retrieval, electronic adaptation, computer software, or by similar or dissimilar methodology now known or hereafter developed. The use of general descriptive names, registered names, trademarks, service marks, etc. in this publication does not imply, even in the absence of a specific statement, that such names are exempt from the relevant protective laws and regulations and therefore free for general use. The publisher, the authors and the editors are safe to assume that the advice and information in this book are believed to be true and accurate at the date of publication. Neither the publisher nor the authors or the editors give a warranty, express or implied, with respect to the material contained herein or for any errors or omissions that may have been made. Printed on acid-free paper This Springer imprint is published by Springer Nature The registered company is Springer International Publishing AG The registered company address is: Gewerbestrasse 11, 6330 Cham, Switzerland
Contents
1 Peptide Synthesis of Libraries of Non-natural Amino Acids . . . 1.1 Statement of the Problem . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1.2 Solid-Phase Organic Synthesis . . . . . . . . . . . . . . . . . . . . . . . . 1.2.1 Specific of SPOS . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1.2.2 Polymers Used . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1.2.3 Methodology and Principal Stages of SPOS . . . . . . . . 1.3 Practical Implementation of the Task . . . . . . . . . . . . . . . . . . . 1.3.1 Stage 1: Immobilization of Amino Acids on Supports 1.3.2 Stage 2: Removal of Protective Groups . . . . . . . . . . . 1.3.3 Synthesis of Heterocycles with a Readily Leaving Group . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1.3.4 Realization of Stage 3 (Solid-Phase Nucleophilic Substitution) and Stage 4 (Product Removal from Polymer Support) . . . . . . . . . . . . . . . . . . . . . . . . 1.4 Conclusions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
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