Momcilo Miljkovic Electrostatic and Stereoelectronic Effects in Carbohydrate Chemistry Electrostatic and Stereoelectronic Effects in Carbohydrate Chemistry Momcilo Miljkovic Electrostatic and Stereoelectronic Effects in Carbohydrate Chemistry Momcilo Miljkovic Pennsylvania State University Hershey, Pennsylvania, USA ISBN 978-1-4614-8267-3 ISBN 978-1-4614-8268-0 (eBook) DOI 10.1007/978-1-4614-8268-0 Springer New York Heidelberg Dordrecht London Library of Congress Control Number: 2013955044 © Springer Science+Business Media New York 2014 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 Exempted from this legal reservation are brief excerpts in connection with reviews or scholarly analysis or material supplied specifically for the purpose of being entered and executed on a computer system, for exclusive use by the purchaser of the work Duplication of this publication or parts thereof is permitted only under the provisions of the Copyright Law of the Publisher’s location, in its current version, and permission for use must always be obtained from Springer Permissions for use may be obtained through RightsLink at the Copyright Clearance Center Violations are liable to prosecution under the respective Copyright Law 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 While the advice and information in this book are believed to be true and accurate at the date of publication, neither the authors nor the editors nor the publisher can accept any legal responsibility for any errors or omissions that may be made The publisher makes no warranty, express or implied, with respect to the material contained herein Printed on acid-free paper Springer is part of Springer Science+Business Media (www.springer.com) To the memory of my parents Prof Dr Adam Miljkovic´ and Dr Dragoslava Miljkovic´ In Memoriam Dr Momcilo Miljkovic was born on December 12, 1931, in Belgrade, Serbia He was the son of physicians Dr Adam Miljkovic and Dr Dragoslava Miljkovic At the age of 14, his father bought him a chemistry kit, and soon Momcilo was passionately conducting chemistry experiments at home in the family’s kitchen He became completely fascinated with chemistry, reading college textbooks while still in high school, and developing a reputation as a young chemist, so much so that his chemistry teacher would look to him in class for his approval or disapproval regarding the correctness of her lectures Dr Momcilo Miljkovic went on to pursue a B.S in chemistry at The University of Belgrade, Serbia, and later was awarded a Ph.D in Chemistry in 1965 at the Eidgenossische Technische Hochschule (Swiss Federal Institute of Technology) in Zurich, Switzerland He pursued post-doctoral studies under Dr Vladimir Prelog (Nobel Laureate) at ETH, while his informal mentor was Dr Leopold Ruzicka (Nobel Laureate) Another post-doctoral position brought him to the United States to the Department of Biochemistry at Duke University, and a year later he took a position as Assistant Professor in The Department of Biochemistry in the College of Medicine at The Pennsylvania State University It is here that he spent over 40 years of his life, conducting research in carbohydrate chemistry as well as teaching graduate students and medical students Towards the end of his life, he preoccupied himself with writing He published his first book Carbohydrates: Synthesis, Mechanisms, and Stereoelectronic Effects in 2010 He was particularly excited about writing Electrostatic and Stereoelectronic Interactions in Carbohydrate Chemistry due to the novelty of the material Further, writing helped him focus away from his own terminal illness, giving him a newfound purpose in the latter stages of his life vii Acknowledgments Several details were left unfinished, and completed after the author’s death Without the time, effort, and expertise of Dr Stephen Benkovic, Department of Chemistry at The Pennsylvania State University, in editing portions of this book, it could not have been published Nor would this book have seen the light of day without the cheerful persistence of Dr Marko Miljkovic´, who nursed his father through his final illness, sorted through manuscripts left by his father, consulted with carbohydrate chemists when details in the manuscript were unclear, and meticulously edited portions of this book ix .. .Electrostatic and Stereoelectronic Effects in Carbohydrate Chemistry Momcilo Miljkovic Electrostatic and Stereoelectronic Effects in Carbohydrate Chemistry Momcilo Miljkovic... book Carbohydrates: Synthesis, Mechanisms, and Stereoelectronic Effects in 2010 He was particularly excited about writing Electrostatic and Stereoelectronic Interactions in Carbohydrate Chemistry. .. (intermolecular electrostatic interactions) or can be within a single molecule (intramolecular electrostatic interactions) The electrostatic interactions can be stabilizing or destabilizing in