The Organic Chemistry of Sugars - D.E Levy, P. Fugedi.pdf - CHEMIA - książki - qazar

Organic Chemistry

of Sugars

The

Organic Chemistry

of Sugars

Edited by

Daniel E. Levy

Péter Fügedi

Boca Raton London New York

A CRC title, part of the Taylor & Francis imprint, a member of the

Taylor & Francis Group, the academic division of T&F Informa plc.

The

Published in 2006 by

CRC Press

Taylor & Francis Group

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Boca Raton, FL 33487-2742

CRC Press is an imprint of Taylor & Francis Group

No claim to original U.S. Government works

Printed in the United States of America on acid-free paper

10987654321

International Standard Book Number-10: 0-8247-5355-0 (Hardcover)

International Standard Book Number-13: 978-0-8247-5355-9 (Hardcover)

Library of Congress Card Number 2005049282

This book contains information obtained from authentic and highly regarded sources. Reprinted material is quoted with

permission, and sources are indicated. A wide variety of references are listed. Reasonable efforts have been made to publish

reliable data and information, but the author and the publisher cannot assume responsibility 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

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Library of Congress Cataloging-in-Publication Data

The organic chemistry of sugars / edited by Daniel E. Levy & Péter Fügedi.

p. cm.

Includes bibliographical references and index.

ISBN 0-8247-5355-0

1. Carbohydrates. 2. Glycosides. 3. Oligosaccharides. I. Levy, D.E. (Daniel E.) II. Fügedi, Péter, Ph. D.

QD321.074 2006

547'.78--dc22

2005049282

Taylor & Francis Group

is the Academic Division of T&F Informa plc.

Visit the Taylor & Francis Web site at

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and the CRC Press Web site at

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Dedications

This book is dedicated to those who devoted their careers to the

advancement of the organic chemistry of sugars

and to

Jennifer, Aaron, Joshua and Dahlia

Enik ˝ and P ´ ter

for their love, understanding and support

during the preparation of this work,

and to

the memory of A ´ kos.

Foreword

From ahistorical perspective, no single class of organic compounds has shared the same

impact on the evolution of stereochemistry as sugar molecules.Compared with the remarkable

synthesisofthe ﬁrst natural product, urea, by Friedrich W¨ hler in 1828, the total synthesis of

glucose by Emil Fischer in 1895 was ahallmark event in the annals of organic synthesis. As

biological activity began to be associated with more complexnatural products such as

alkaloids, steroids and various metabolitesbythe middle of the twentieth century, interest in

sugars as small molecule polyols shiftedtothe study of polysaccharides and their degradation

products.

By the mid-1960s, synthetic carbohydrate chemistry was conﬁned to asmall subgroup of

organic chemists,who studied methods of interconversion and functional group manipulation in

conjunction with the structure elucidation of antibiotics containing sugars. Soon, mostnaturally

occurring sugars, including deoxy, aminodeoxy and branched ones, had been synthesized. As a

result, sugar molecules had become ideal substrates to test out new bond-forming methods,

particularlybecause of theirconformational properties, andhe propensity of spatially

predisposed hydroxyl groups. Sugars became aplaygroundtovalidateconcepts related to

anchimeric assistance in conjunction with the synthesis of aminodeoxy component sugars in

various natural products.

An altogether different view of sugarsand their potential as chiral building blocks was

introduced in the mid-1970s. This was to have an important impact on the thought process

relating to organic synthesis in general. This marked the beginninganewera of rapprochement,

integrating sugarchemistry in mainstreamorganic chemistry. Notonly were the sugar

components of complex natural products readily madebysynthesis, but the entire framework

of the “non-sugar,” and admittedly the morechallenging part, could also be made from sugar

building blocks or “chirons.”

By the 1980s, the advent of reagent methodology and asymmetric synthesis once again

shifted the paradigm of thinking in considering complex natural product assembly from smaller

components. Today, it is more practical, in many cases, to consider other innovative

approaches to total synthesis without necessarily relying on sugars as chiral,nonracemic

starting materials. In fact, de novo syntheses of even raresugarsisnow possible by relyingon

efﬁcient catalytic asymmetric processes. In adifferent context, the uniquechemical and

physicochemicalproperties of sugars have propelled them into new and exciting areas of

application in molecular biology, drug design, materials, and other ﬁelds of direct impact on our

quality of life.

Arenaissance period for sugars is in full swing with the creation of new subdisciplines that

bridge chemistry and biology. New areas relating to glycochemistry and glycobiology have

emergedinconjunction with the important interface with proteins, nucleic acids, and other

biological macromolecules. The historyofsugar chemistryhas come full circle since the grandeur

of the EmilFisher era, and the exciting, purely chemical activities of the latter part of the twentieth

century. Sugar chemistry has emergedasapivotal link betweenmolecular recognitionand

biological events in conjunction with vital life processes.

The preceding preamble to asugar chemistrypanoramawas necessary for me to introduce

this timely monograph to the readers. In The Organic Chemistry of Sugars,authors/editors

Daniel Levy and P´ ter F¨ gedi have captured the beauty of thispanorama in acollection of 16

authoritative chapterscovering the essence of almost every aspectofsynthetic sugar chemistry.

The Organic Chemistry of Sugars - D.E Levy, P. Fugedi.pdf

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