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LC-NMR: Expanding the Limits of Structure Elucidation 2nd Edition

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Nina C. Gonnella

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1138493406

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978-1138493407

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2nd edition | 2020

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ISBN: 978-1138493407 SKU: BS1367 Category: Chemistry Tags: Chemistry, LC-NMR, LC-NMR: Expanding the Limits of Structure Elucidation, LC-NMR: Expanding the Limits of Structure Elucidation 2nd Edition, Pharmacology
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LC-NMR: Expanding the Limits of Structure Elucidation 2nd Edition

LC-NMR: Expanding the Limits of Structure Elucidation Second Edition (Chromatographic Science Series):

The isolation and structural characterization of substances present at very low concentrations, as is necessary to satisfy regulatory requirements for pharmaceutical drug degradants and impurities, can present scientific challenges. The coupling of HPLC with NMR spectroscopy has been at the forefront of cutting-edge technologies to address these issues. LC-NMR: Expanding the Limits of Structure Elucidation presents a comprehensive overview of key concepts in HPLC and NMR that are required to achieve definitive structure elucidation with very low levels of analytes. Because skill sets from both of these highly established disciplines are involved in LC-NMR, the author provides introductory background to facilitate readers’ proficiency in both areas, including an entire chapter on NMR theory.

The much-anticipated second edition provides guidance in setting up LC-NMR systems, discussion of LC methods that are compatible with NMR, and an update on recent hardware and software advances for system performance, such as improvements in magnet design, probe technology, and solvent suppression techniques that enable unprecedented mass sensitivity in NMR. This edition features methods to quantify concentration and assess purity of isolated metabolites on the micro scale and incorporates computational approaches to accelerate the structure elucidation process. The author also includes implementation and application of qNMR and automated and practical use of computational chemistry combined with QM and DFT to predict highly accurate NMR chemical shifts. The text focuses on current developments in chromatographic-NMR integration, with particular emphasis on utility in the pharmaceutical industry. Applications include trace analysis, analysis of mixtures, and structural characterization of degradation products, impurities, metabolites, peptides, and more. The text discusses novel uses and emerging technologies that challenge detection limits as well future directions for this important technique. This book is a practical primary resource for NMR structure determination―including theory and application―that guides the reader through the steps required for isolation and NMR structure elucidation on the micro scale.


Additional ISBNs:

∗ eText ISBN: 1351023721, 978-1351023726, 9781351023726

  • See additional information on the Amazon.

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Contents

LC-NMR: Expanding the Limits of Structure Elucidation 2nd Edition:

Cover
Half Title
Series Page
Title Page
Copyright Page
Dedication
Table of Contents
Foreword
Preface
Author
Chapter 1. Introduction to LC-NMR
1.1. Historical Review
1.2. Flow and NMR
1.3. Setting up the LC-NMR System
1.3.1. Continuous-Flow Mode
1.3.2. Direct Stopped-Flow Mode
1.3.3. Storage Mode
1.3.4. Calibrating the System
1.3.5. Preparation of a Solid-Phase Extraction System
1.3.6. Adding More Sample to a Cartridge
1.4. Solvent Requirements in LC-NMR
1.5. Solvent Suppression and Referencing
1.6. The Deuterium Lock
1.7. The Solvent-Gradient Ramp
1.8. Diffusion
1.9. Shimming
1.10. Acquisition Parameters
1.11. Chemical-shift Tracking
1.12. Other Considerations
1.13. Sources of Error
1.14. Summary
Chapter 2. NMR Theory
2.1. Magnetic Properties of Nuclei
2.2. Data Acquisition
2.3. Relaxation of Nuclei
2.3.1. Spin-Lattice Relaxation Time T1 (Longitudinal)
2.3.1.1. Relaxation and Molecular Motion
2.3.1.2. Dipole-Dipole Interaction “Through Space”
2.3.1.3. Paramagnetic Relaxation
2.3.1.4. Chemical Shift Anisotropy Relaxation
2.3.1.5. Scalar Coupling Relaxation
2.3.1.6. Electric Quadrupolar Relaxation
2.3.1.7. Spin Rotation
2.3.2. Spin-Spin Relaxation Time T2 (Transverse)
2.4. The Chemical Shift
2.5. Spin Coupling
2.6. Nuclear Overhauser Effect (NOE)
2.6.1. Molecular Weight and Maximum NOE
2.6.2. Time Dependence of NOE – Mixing Times
2.7. Coupling of HPLC with NMR
Chapter 3. Separation Methods
3.1. Modes of Separation
3.2. General Method Development Strategies
3.3. Column Packing Types
3.4. Detector Selection
3.5. RPC Method Development and Compatibility with NMR
3.6. Integration of CE and NMR
3.7. Transitioning from Analytical to Preparative Chromatography
3.8. General Considerations
Chapter 4. NMR Instrumentation and Probe Technologies
4.1. Instrumentation Configuration
4.2. The Magnet
4.3. Room Temperature Flow Probe
4.4. Microcapillary Probes (Room Temperature)
4.4.1. Microcoil Capillary Flow Probes (Room Temperature)
4.4.2. Microcoil Tube Probes (Room Temperature)
4.5. Cryogenically Cooled Probes
4.5.1. Cryo-flow Probe
4.5.2. Cryo-capillary Tube Probe
4.5.3. Affordable Cryogenically Cooled Probes
4.6. Probe Coil Geometries
4.7. Probe Sensitivity Comparison
Chapter 5. NMR-Associated Isolation Technologies
5.1. Stop Flow
5.2. Loop Collector
5.3. Solid-Phase Extraction (SPE)
5.4. Non-chromatographic Flow NMR
5.5. Direct Injection NMR (DI-NMR)
5.5.1. Applications of DI-NMR
5.5.2. Comparisons
5.6. Capillary Electrophoresis and NMR
5.6.1. Modes of Electrophoresis-NMR and Effects on NMR Spectral Properties
5.6.2. NMR Observe Volume
5.6.3. Capillary Electrochromatography (CEC)-NMR
5.6.4. CE-NMR in Practice
Chapter 6. NMR Experiments
6.1. Solvent Suppression
6.2. Structure Elucidation Experiments
6.2.1. Heteronuclear Correlation Experiments (HSQC, HMQC, and HMBC)
6.2.2. Wet Solvent Suppression and 2D NMR
6.2.3. Decoupling and Power Levels in 2D NMR
6.3. NOE Experiments
6.3.1. Sample Considerations
6.3.2. Processing (NOESY and ROESY) 2D Spectra
6.3.3. Chemical/Conformational Exchange
6.3.4. Spin Diffusion (Problematic for Large Molecules)
6.3.5. NOE, Conformational Analysis, and Distance Determination
6.3.6. ROESY – Quantitative Distance Determination
Chapter 7. Applications
7.1. Degradation Products
7.2. Impurities
7.3. Trace Analysis
7.4. Analysis of Mixtures
7.5. Formulation Adduct
7.6. Tautomer Kinetics
7.7. Unstable Products
7.8. Metabolites
7.9. cITP Isolates
7.10. Natural Products
7.11. Proteins/Peptides
Chapter 8. Other Specialized Flow NMR
8.1. NMR and Parallel Detection
8.2. Data Processing and Deconvolution of Parallel Data
8.3. Parallel Probe Construction
8.3.1. Multiplex Four-Coil Probe
8.3.2. Multiplex Dual Probe
8.4. Microprobes
8.5. Advancements in Multiple-Coil Probe Design
8.6. Biological Screening and Flow NMR
8.7. NMR and Microreactors
8.8. Signal-to-Noise Ratio (Microcoils)
8.9. Microprobe Design (Microcoil/Microslot/Microstrip)
8.10. Future Directions
8.10.1. Portable NMR and Sensitivity
8.10.2. DNP and NMR Sensitivity
Chapter 9. Quantitation of Isolated Compounds
9.1. Background of Quantitative NMR (qNMR)
9.2. Comparison of qNMR with HPLC Methods
9.3. Selecting a qNMR Reference Standard
9.3.1. External versus Internal qNMR Reference
9.3.2. Calibration Procedure
9.4. Instrument Settings, Solvent Selection, Rapid Spectral Analysis
9.5. Types of qNMR Calculations
9.5.1. Concentration (ERETIC2)
9.5.2. Mass of Compound (Internal Standard and ERETIC)
9.5.3. Purity
9.6. Applications
Chapter 10. QM/DFT Chemical Shift Prediction
10.1. Computational Methods
10.1.1. Method Evaluation
10.1.2. Systematic Errors
10.2. Statistical Distribution of Chemical Shift Differences (1H, 13C, and 15N NMR)
10.3. NMR Referencing
10.3.1. TMS
10.3.2. Nitromethane/LNH3
10.3.3. Linear Scaling
10.4. Automated Program Development
10.4.1. HiPAS Holistic In-silico Prediction Application Software
10.4.2. DP4, DP4+, and DiCE Diasteromeric In-silico Chiral Elucidation
10.5. Applications
10.5.1. Regioisomers
10.5.2. Tautomers
10.5.3. Natural Products
10.5.4. Assignment Ambiguities
10.5.5. Decomposition Products
10.5.6. Diastereomers
10.6. Summary
Glossary
Index

About the Author

Nina C. Gonnella

Nina C. Gonnella, Ph.D. is a Senior Associate Director at Boehringer Ingelheim (BI) where she heads a molecular structure and solid form informatics group, encompassing NMR Spectroscopy, Mass Spectrometry, Single Crystal X-ray and Computational Chemistry. She has extensive experience leading Pharmaceutical Research and Development groups spanning structural characterization /ligand screening and in-vitro and in-vivo biological studies.

Nina received her Ph.D. in Synthetic Organic Chemistry from the University of Pennsylvania and subsequently held postdoctoral positions at California Institute of Technology and Columbia University. Prior to joining BI, Nina was group leader / manager at Novartis where she established and led an NMR group in areas that included, small molecule characterization, protein-ligand structure elucidation and in-vivo drug metabolism. She has advanced discovery research through application of structure based drug design and ligand based screening technologies to identify and optimize new lead series in both kinase and protease programs. Nina also held a position as adjunct professor at the University of Medicine & Dentistry of NJ (UMDNJ) (Graduate Program). She subsequently joined AbbVie as Group Leader of an NMR-LC-MS group with focus on protein-ligand binding studies. At BI, Nina has advanced BI projects through the development of innovative solutions. She championed solid state NMR as a company-wide Center of Expertise and initiated the acquisition of small molecule single crystal X-ray for global R&D. She introduced “state of the art” performance in integrating LC-NMR and micro-cryo probe NMR technology to enable elucidation of micro-scale degradation products and impurities. Nina initiated and led an international team in the development of powerful commercial ready in-silico structure elucidation programs that use quantum chemistry, density functional theory and probability theory to solve challenging chemical structures. Nina co-founded, organized and chaired a new Gordon Research Conference in “Molecular Structure Elucidation.” She has served on scientific review boards, published over 95 peer review journal articles, authored book chapters, taught courses and presented numerous national and international lectures.

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