Modern NMR Approaches to the Structure Elucidation of Natural Products: Volume 2: Data Acquisition and Applications to Compound Classes
The Ghanian plant Cryptolepis sanguinolenta is the source of a series of fascinating indoloquinoline alkaloids. The most unusual member of this alkaloid series was initially proposed to be a spiro nonacyclic structure, named cryptospirolepine, and was elucidated in 1993 based on the technologies available at that time. There were, however, several annoying attributes to the structure that bothered analysts for the ensuing 22 years. During the two decades that followed the initial work there have been enormous developments in NMR technology. Using new experimental approaches, specifically homodecoupled 1,1- and 1,n-HD-ADEQUATE NMR experiments developed in 2014, the structure of only a 700 µg sample of cryptospirolepine has been revised and is shown on the cover of this volume. The confluence of the NMR technological and methodological advances that allowed the revision of the structure of cryptospirolepine using a submilligram sample seems a fitting example for this book, which is dedicated to the NMR characterization of various classes of natural products.
Volume 2 considers data processing and algorithmic based analyses tailored to natural product structure elucidation and reviews the application of NMR to the analysis of a series of different natural product families including marine natural products, terpenes, steroids, alkaloids and carbohydrates. Volume 1 discusses contemporary NMR approaches including optimized and future hardware and experimental approaches to obtain both the highest quality and most appropriate spectral data for analysis. These books, bringing together acknowledged experts, uniquely focus on the combination of experimental approaches and modern hardware and software applied to the structure elucidation of natural products. The volumes will be an essential resource for NMR spectroscopists, natural product chemists and industrial researchers working on natural product analysis or the characterization of impurities and degradation products of pharmaceuticals that can be as scarce as natural product samples.
Modern NMR Approaches to the Structure Elucidation of Natural Products: Volume 2: Data Acquisition and Applications to Compound Classes, The Royal Society of Chemistry, 2016.
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Chapter 1: Application of the Nuclear Overhauser Effect to the Structural Elucidation of Natural Productsp1-38ByR. R. Gil;R. R. GilCarnegie Mellon University, Department of Chemistry4400 Fifth AvenuePittsburghPA 15213-3890USA[email protected]Search for other works by this author on:A. Navarro-VázquezA. Navarro-VázquezInstitute of Organic Chemistry and Institute for Biological Interfaces Karlsruhe, Institute of Technology (KIT)Fritz-Haber-Weg 676131 KarlsruheGermany[email protected]Search for other works by this author on:
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Chapter 2: Assigning Molecular Configuration by Nuclear Magnetic Resonancep39-70ByKirk R. Gustafson;Kirk R. GustafsonMolecular Targets LaboratoryBuilding 562, Room 201Center for Cancer ResearchNational Cancer InstituteFrederickMD 21702USA[email protected]Search for other works by this author on:Susanna T. S. Chan;Susanna T. S. ChanMolecular Targets LaboratoryBuilding 562, Room 201Center for Cancer ResearchNational Cancer InstituteFrederickMD 21702USA[email protected]Search for other works by this author on:Yizhou LiuYizhou LiuMerck & Co., Inc., NMR Structure Group, Process and Development ResearchMailstop RY-800 D-133, 126 E. Lincoln Ave.RahwayNJ 07065USASearch for other works by this author on:
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Chapter 3: Nuclear Magnetic Resonance Experiments Applicable to the Elucidation and Characterization of Nitrogenous Natural Products: 1H–15N Heteronuclear Shift Correlation Methodsp71-116ByJosep Saurí;Josep SauríMerck & Co., Inc., Process & Analytical Chemistry, NMR Structure ElucidationRahway, NJ 07065USA[email protected]Search for other works by this author on:Antony J. Williams;Antony J. WilliamsChemConnector Inc.Wake Forest, NC 27587USASearch for other works by this author on:Gary E. MartinGary E. MartinMerck & Co., Inc., Process & Analytical Chemistry, NMR Structure ElucidationRahway, NJ 07065USA[email protected]Search for other works by this author on:
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Chapter 4: Application of Residual Dipolar Couplings to the Structural Analysis of Natural Productsp117-176ByR. R. Gil;R. R. GilCarnegie Mellon University, Department of Chemistry4400 Fifth AvenuePittsburghPA 15213-3890USA[email protected]Search for other works by this author on:A. Navarro-VázquezA. Navarro-VázquezInstitute of Organic Chemistry and Institute for Biological Interfaces Karlsruhe, Institute of Technology (KIT)Fritz-Haber-Weg 676131 KarlsruheGermany[email protected]Search for other works by this author on:
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Chapter 5: Applications of High-resolving Power, High-accuracy Mass Spectrometry for the Structural Elucidation of Natural Productsp177-198ByWendy ZhongWendy ZhongAnalytical Research & DevelopmentMerck Research Laboratories 126 E. Lincoln Ave.RahwayNJ 07065USASearch for other works by this author on:
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Chapter 6: Current Pulse Sequence Developments in Small-molecule Nuclear Magnetic Resonance Spectroscopyp199-250ByTeodor ParellaTeodor ParellaServei de Ressonància Magnètica Nuclear, Facultat de Ciències, Universitat Autònoma de BarcelonaE-08193 Bellaterra (Barcelona), CataloniaSpain[email protected]Search for other works by this author on:
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Chapter 7: Terpenes: Mono-, Sesqui-, and Higher Terpenesp251-274ByRaul G. EnriquezRaul G. EnriquezInstituto de Quimica, Universidad Nacional Autonoma de MexicoMexicoD.F. 04100MexicoSearch for other works by this author on:
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Chapter 8: Nuclear Magnetic Resonance of Steroidsp275-314ByMartin Jaeger;Martin JaegerNiederrhein University of Applied Sciences, Department of Chemistry, Instrumental Analytical Chemistry and ILOC Institute for Coatings and Surface ChemistryFrankenring 20D-47798 KrefeldGermany[email protected]Search for other works by this author on:Ruud L. E. G. AspersRuud L. E. G. AspersRadboud University, Institute for Molecules and Materials, Biophysical ChemistryHeyendaalseweg 1356525 AJ NijmegenThe NetherlandsSearch for other works by this author on:
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Chapter 9: Nuclear Magnetic Resonance Experiments Applicable to the Elucidation and Characterization of Alkaloid Structures Part I: Direct 1H–13C Heteronuclear Shift Correlation and Establishing Contiguous Protonated Carbon Spin Systemsp315-357ByJosep Saurí;Josep SauríMerck & Co., Inc., Process & Analytical Chemistry, NMR Structure ElucidationRahway, NJ 07065USA[email protected]Search for other works by this author on:Gary E. MartinGary E. MartinMerck & Co., Inc., Process & Analytical Chemistry, NMR Structure ElucidationRahway, NJ 07065USA[email protected]Search for other works by this author on:
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Chapter 10: Nuclear Magnetic Resonance Experiments Applicable to the Elucidation and Characterization of Alkaloid Structures Part II: Advanced Techniques for the Identification of Adjacent Carbons Using H2BC, 1,1-ADEQUATE, and Variantsp358-402ByJosep Saurí;Josep SauríMerck & Co., Inc., Process & Analytical Chemistry, NMR Structure ElucidationRahwayNJ 07065USA[email protected]Search for other works by this author on:Gary E. MartinGary E. MartinMerck & Co., Inc., Process & Analytical Chemistry, NMR Structure ElucidationRahwayNJ 07065USA[email protected]Search for other works by this author on:
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Chapter 11: Nuclear Magnetic Resonance Case Studies in Marine Natural Productsp403-439ByAngela A. Salim;Angela A. SalimDivision of Chemistry and Structural Biology, Institute for Molecular Bioscience, The University of QueenslandSt Lucia, Queensland 4072Australia[email protected]Search for other works by this author on:Andrew M. Piggott;Andrew M. PiggottDivision of Chemistry and Structural Biology, Institute for Molecular Bioscience, The University of QueenslandSt Lucia, Queensland 4072Australia[email protected]Search for other works by this author on:Robert J. CaponRobert J. CaponDivision of Chemistry and Structural Biology, Institute for Molecular Bioscience, The University of QueenslandSt Lucia, Queensland 4072Australia[email protected]Search for other works by this author on:
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Chapter 12: Nuclear Magnetic Resonance Case Studies in Microbial Natural Productsp440-485ByAndrew M. Piggott;Andrew M. PiggottDivision of Chemistry and Structural Biology, Institute for Molecular Bioscience, The University of QueenslandSt LuciaQueensland 4072Australia[email protected]Search for other works by this author on:Angela A. Salim;Angela A. SalimDivision of Chemistry and Structural Biology, Institute for Molecular Bioscience, The University of QueenslandSt LuciaQueensland 4072Australia[email protected]Search for other works by this author on:Robert J. CaponRobert J. CaponDivision of Chemistry and Structural Biology, Institute for Molecular Bioscience, The University of QueenslandSt LuciaQueensland 4072Australia[email protected]Search for other works by this author on:
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Chapter 13: Nuclear Magnetic Resonance in Saponin Structure Elucidationp486-501ByAntonio Jorge Ribeiro da Silva;Antonio Jorge Ribeiro da SilvaInstituto de Pesquisas de Produtos Naturais Walter B. MorsAvenida Carlos Chagas Filho373, Edifício do CCSBloco H CEP 21941-902 Rio de Janeiro, RJBrazil[email protected]Search for other works by this author on:Ricardo Moreira Borges;Ricardo Moreira BorgesInstituto de Pesquisas de Produtos Naturais Walter B. MorsAvenida Carlos Chagas Filho373, Edifício do CCSBloco H CEP 21941-902 Rio de Janeiro, RJBrazil[email protected]Search for other works by this author on:Vitor SoaresVitor SoaresInstituto de Pesquisas de Produtos Naturais Walter B. MorsAvenida Carlos Chagas Filho373, Edifício do CCSBloco H CEP 21941-902 Rio de Janeiro, RJBrazil[email protected]Search for other works by this author on:
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Chapter 14: Increasing the Adoption of Advanced Techniques for the Structure Elucidation of Natural Productsp502-507ByGary E. Martin;Gary E. MartinMerck Sharp and Dohme, Process & Analytical Chemistry, NMR Structure ElucidationRahwayNJ 07065USA[email protected]Search for other works by this author on:David RovnyakDavid RovnyakSearch for other works by this author on:
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