Comprehensive Chiroptical Spectroscopy: Applications in Stereochemical Analysis of Synthetic Compounds, Natural Products, and Biomolecules

The definitive guide to chiroptical spectroscopy

Providing an introduction to the methods of chiroptical spectroscopy, this two–volume set presents comprehensive coverage of the most important and up–to–date methods of dealing with chiral molecules, which can discriminate between left and right circularly polarized light. Addressing basic principles, instrumentation, and applications in the natural sciences, Comprehensive Chiroptical Spectroscopy is the only book of its kind to provide cutting–edge, in–depth coverage of recent developments and frontier topics in the field, looking at the most important applications of chiroptical spectroscopy to problems in organic and inorganic chemistry, biochemistry, and structural biology.

Topics covered in the second volume include:

Aromatic chromophores

Exciton chirality method

Inorganic systems

Chiral natural products

Peptides, proteins, nucleic acids, and carbohydrates

Drug and natural product binding to nucleic acids

And much more

With each chapter written by one or more leading authorities in the field, Comprehensive Chiroptical Spectroscopy presents the ideal tools needed to determine chiral molecular structures and associated molecular properties, making it a must–have for both students and researchers.

PREFACE xi

CONTRIBUTORS xiii

PART I A HISTORICAL OVERVIEW 1

1 THE FIRST DECADES AFTER THE DISCOVERY OF CD AND ORD BY AIME COTTON IN 1895 3
Peter Laur

PART II ORGANIC STEREOCHEMISTRY 37

2 SOME INHERENTLY CHIRAL CHROMOPHORES EMPIRICAL RULES AND QUANTUM CHEMICAL CALCULATIONS 39
Marcin Kwit, Pawel Skowronek, Jacek Gawronski, Jadwiga Frelek, Magdalena Woznica, and Aleksandra Butkiewicz

3 ELECTRONIC CD OF BENZENE AND OTHER AROMATIC CHROMOPHORES FOR DETERMINATION OF ABSOLUTE CONFIGURATION 73
Tibor Kurtan, Sandor Antus, and Gennaro Pescitelli

4 ELECTRONIC CD EXCITON CHIRALITY METHOD: PRINCIPLES AND APPLICATIONS 115
Nobuyuki Harada, Koji Nakanishi, and Nina Berova

5 CD SPECTRA OF CHIRAL EXTENDED p–ELECTRON COMPOUNDS: THEORETICAL DETERMINATION OF THE ABSOLUTE STEREOCHEMISTRY AND EXPERIMENTAL VERIFICATION 167
Nobuyuki Harada and Shunsuke Kuwahara

6 ASSIGNMENT OF THE ABSOLUTE CONFIGURATIONS OF NATURAL PRODUCTS BY MEANS OF SOLID–STATE ELECTRONIC CIRCULAR DICHROISM AND QUANTUM MECHANICAL CALCULATIONS 217
Gennaro Pescitelli, Tibor Kurtan, and Karsten Krohn

7 DYNAMIC STEREOCHEMISTRY AND CHIROPTICAL SPECTROSCOPY OF METALLO–ORGANIC COMPOUNDS 251
James W. Canary and Zhaohua Dai

8 CIRCULAR DICHROISM OF DYNAMIC SYSTEMS: SWITCHING MOLECULAR AND SUPRAMOLECULAR CHIRALITY 289
Angela Mammana, Gregory T. Carroll, and Ben L. Feringa

9 ELECTRONIC CIRCULAR DICHROISM OF SUPRAMOLECULAR SYSTEMS 317
Cheng Yang and Yoshihisa Inoue

10 THE ONLINE STEREOCHEMICAL ANALYSIS OF CHIRAL COMPOUNDS BY HPLC–ECD COUPLING IN COMBINATION WITH QUANTUM–CHEMICAL CALCULATIONS 355
Gerhard Bringmann, Daniel Gotz, and Torsten Bruhn

11 DETERMINATION OF THE STRUCTURES OF CHIRAL NATURAL PRODUCTS USING VIBRATIONAL CIRCULAR DICHROISM 387
Prasad L. Polavarapu

12 DETERMINATION OF MOLECULAR ABSOLUTE CONFIGURATION: GUIDELINES FOR SELECTING A SUITABLE CHIROPTICAL APPROACH 421
Stefano Superchi, Carlo Rosini, Giuseppe Mazzeo, and Egidio Giorgio

PART III INORGANIC STEREOCHEMISTRY 449

13 APPLICATIONS OF ELECTRONIC CIRCULAR DICHROISM TO INORGANIC STEREOCHEMISTRY 451
Sumio Kaizaki

PART IV BIOMOLECULES 473

14 ELECTRONIC CIRCULAR DICHROISM OF PROTEINS 475
Robert W. Woody

15 ELECTRONIC CIRCULAR DICHROISM OF PEPTIDES 499
Claudio Toniolo, Fernando Formaggio, and Robert W. Woody

16 ELECTRONIC CIRCULAR DICHROISM OF PEPTIDOMIMETICS 545
Claudio Toniolo and Fernando Formaggio

17 CIRCULAR DICHROISM SPECTROSCOPY OF NUCLEIC ACIDS 575
Jaroslav Kypr, Iva Kejnovska, Klara Bednarova, and Michaela Vorlickova

18 ELECTRONIC CIRCULAR DICHROISM OF PEPTIDE NUCLEIC ACIDS AND THEIR ANALOGUES 587
Roberto Corradini, Tullia Tedeschi, Stefano Sforza, and Rosangela Marchelli

19 CIRCULAR DICHROISM OF PROTEIN NUCLEIC ACID INTERACTIONS 615
Donald M. Gray

20 DRUG AND NATURAL PRODUCT BINDING TO NUCLEIC ACIDS ANALYZED BY ELECTRONIC CIRCULAR DICHROISM 635
George A. Ellestad

21 PROBING HSA AND AGP DRUG–BINDING SITES BY ELECTRONIC CIRCULAR DICHROISM 665
Miklos Simonyi

22 CONFORMATIONAL STUDIES OF BIOPOLYMERS, PEPTIDES, PROTEINS, AND NUCLEIC ACIDS. A ROLE FOR VIBRATIONAL CIRCULAR DICHROISM 707
Timothy A. Keiderling and Ahmed Lakhani

23 STRUCTURE AND BEHAVIOR OF BIOMOLECULES FROM RAMAN OPTICAL ACTIVITY 759
Laurence D. Barron and Lutz Hecht

24 OPTICAL ROTATION, ELECTRONIC CIRCULAR DICHROISM, AND VIBRATIONAL CIRCULAR DICHROISM OF CARBOHYDRATES AND GLYCOCONJUGATES 795
Tohru Taniguchi and Kenji Monde

25 ELECTRONIC CIRCULAR DICHROISM IN DRUG DISCOVERY 819
Carlo Bertucci and Marco Pistolozzi

INDEX 843

Nina Berova is a Research Professor in the Department of Chemistry at Columbia University. She has been a coeditor of the journal Chirality (Wiley) since 1998.

Prasad L. Polavarapu is currently a Professor of Chemistry at Vanderbilt University.

Koji Nakanishi is one of the world′s leading natural products chemists and was editor of the journal, The Chemical Record (Wiley). He retired from Columbia University in 2007, but continues to conduct research.

Robert W. Woody is an Emeritus Professor at Colorado State University.