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E-grāmata: Thin Layer Chromatography in Chiral Separations and Analysis

Edited by Joseph Sherma (Lafayette College, Easton, Pennsylvania, USA), Edited by Teresa Kowalska

Formāts: 436 pages
Izdošanas datums: 22-Jun-2007
Izdevniecība: CRC Press Inc
ISBN-13: 9780849343964

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Formāts: 436 pages
Izdošanas datums: 22-Jun-2007
Izdevniecība: CRC Press Inc
ISBN-13: 9780849343964

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Thin layer chromatography (TLC) is well suited for performing enantioseparations for research as well as larger-scale applications. A fast, inexpensive, and versatile separation technique, there are many practical considerations that contribute to its effectiveness. Thin Layer Chromatography in Chiral Separations and Analysis is the first book to focus solely on the theory, capabilities, and applications of TLC for direct and indirect enantioseparations.

The first part of the book examines the fundamental principles of chirality and TLC. It describes the necessary materials, laboratory equipment, procedures, and strategies for the separation, quantification, isolation, and analysis of chiral compounds. The second part evaluates the real-world enantioseparations and densitometric analyses. Emphasizing pharmaceutical applications, the book discusses chiral separation mechanisms and methods for analyzing the chiral purity of diastereoisomers, amino acids, beta-blockers, and NSAIDS. Topics also include commercial stationary phases and chiral modifiers of mobile phases.

Thin Layer Chromatography in Chiral Separations and Analysis presents a unified perspective of theory and experimental details underlying the collective developments in the field. The book offers scientists in a variety of disciplines and levels of expertise a complete guide to understanding the current and potential applications of chiral TLC.

Preface

Editors

xiii

Contributors

Overview of the Field of Chiral TLC and Organization of the Book

(10)

Teresa Kowalska

Joseph Sherma

Chirality Background

(1)

Basic Strategies of Chromatographic Enantioseparations

(1)

The Areas of Primary Demand for Enantioseparations

(3)

The Role of TLC

(1)

Organization of the Book

(3)

Epilogue

(1)

References

(1)

Chirality

(32)

Piotr Kus

Aleksander Sochanik

Introduction

(3)

Chirality in Nature

(1)

Methods for Determining Compounds' Stereochemistry

(8)

Polarimetric Methods

(3)

Spectroscopic Methods

(5)

On the Methods of Obtaining Stereoisomers

(2)

Stereochemistry of Organic Compounds

(13)

Alkanes and Cycloalkanes

(5)

Alkenes

(1)

Aromatic Compounds

(2)

Heterocyclic Compounds

(1)

Stereochemistry (Chirality) of Organic Compounds with Heteroatoms Other than Oxygen (e.g., Nitrogen, Phosphorus, Sulfur, and Silica)

(4)

Chirality of Coordination Compounds and Chiral Polymers

(1)

Conclusion

(4)

References

(3)

Commercial Precoated Layers for Enantiomer Separations and Analysis

(22)

Joseph Sherma

Introduction

(1)

Chiral Stationary Phases

(10)

Unmodified Native and Microcrystalline Cellulose

(2)

Acetylated Cellulose

(1)

Home-Impregnated Commercial Layers

(1)

Silica Gel

(1)

Amino-Bonded Silica Gel

(1)

Commercially Impregnated Chiralplates

(2)

Control of Optical Purity of L-dopa

(1)

Enantiomer Separation of D,L-Penicillamine

(1)

Enantiomer Separation of a-Hydroxycarboxylic Acids

(1)

Enantiomer Separation of Proteinogenic Amino Acids

(1)

Optical Purity Control of D-Penicillamine

(1)

Separation of Aspartame and Its Precursor Stereoisomers

(1)

Enantiomeric Separation of Dipeptides

(1)

Separation of Enantiomeric α-Methylamino Acids

(1)

Separation of Enantiomeric α-Alkyl and N-Formyl Amino Acids

(1)

Separation of Halogenated Amino Acid Enantiomers

(1)

Nonchiral Plates Used with Chiral Mobile Phases

(3)

Silica Gel

(1)

C-18 and C-18W Bonded Silica Gel

(1)

C-2 Bonded Silica Gel

(1)

Diphenyl-Bonded Silica Gel

(1)

Diol-Bonded Silica Gel

(1)

Enantiomer Separations Using Diastereomeric Derivatives

(2)

Silica Gel

(1)

Reversed Phase Chemically Bonded Silica Gel

(1)

Quantitative Analysis of TLC-Separated Enantiomers by Densitometry

(5)

Chiralplates

(1)

C-8 Chemically Bonded Silica Gel

(1)

References

(3)

Planar Chromatographic Enantioseparations on Noncommercial CSPs

(46)

Luciano Lepri

Alessandra Cincinelli

Massimo Del Bubba

Introduction

(1)

Cellulose

(1)

Cellulose Triacetate

(20)

Preparation of Noncommercial Layers of MCTA + Silica Gel 60GF254

(1)

Analytical Applications

(18)

Cellulose Tribenzoate

(4)

Preparation of Noncommercial Layers of CTB + Silica Gel 60GF254

(1)

Analytical Applications

(3)

Cellulose Tricarbamate

(2)

Preparation of Cellulose Tricarbamate Derivatives and Noncommercial Plates

(1)

Analytical Applications

(1)

Chitin and Chitosan

(1)

Molecular Imprinting Techniques

(10)

Preparation of MIPs Stationary Phases

(1)

Preparation of Synthetic Polymers Imprinted with L- or D-Phenylalanine Anilide (L- or D-Phe-An)

(1)

Preparation of Synthetic Polymers Imprinted with Quinine

(1)

Preparation of Synthetic Polymers Imprinted with (+)-Ephedrine, (+)-Pseudoephedrine, and (+)-Norephedrine

(1)

Preparation of Synthetic Polymers Imprinted with R-(+)-Propranolol, S-(+)-Naproxen, and 5-(-)-Timolol

(1)

Preparation of Noncommercial Layers of MIPs

(1)

Analytical Applications

(6)

β-Cyclodextrin (β-CD)-Bonded Stationary Phases

104

(7)

Preparation of Noncommercial Layers of β-CD-Bonded Silica Gel

104

(2)

Analytical Applications

106

(1)

References

107

(4)

Planar Chromatography Enantioseparations on Noncommercial CCSPs

111

(36)

Luciano Lepri

Alessandra Cincinelli

Massimo Del Bubba

Introduction

111

(1)

Silanized Silica Gel Plates Impregnated with Metal Complexes of a Chiral Selector

112

(8)

Preparation of Noncommercial Plates and Their Applications

112

(8)

Silica Gel Plates Coated with the Copper (II) Complex of Enantiomeric Amino Acids

120

(1)

Silica Gel Coated with Acid or Basic Chiral Selectors

121

(5)

Silica Gel Coated with Amino Acids as Chiral Selectors

126

(12)

Acidic and Basic Amino Acids as Chiral Selectors

127

(5)

Neutral Amino Acids as Chiral Selectors

132

(2)

Mechanism of Chiral Recognition on Silica Gel Layers Coated with Acids, Bases, or Amino Acids as Chiral Selectors

134

(4)

Silica Gel Impregnated with Macrocyclic Antibiotic as Chiral Selectors

138

(3)

Silica Gel Impregnated with Optically Active N-(3,5-Dinitrobenzoyl)Amino Acids (Pirkle Selectors)

141

(6)

References

143

(4)

Chiral Mobile Phase Additives

147

(26)

Danica Agbaba

Branka Ivkovic

Preface

147

(1)

Macrocyclics as Mobile Phase Additives

148

(12)

Cyclodextrins and Their Derivatives as Mobile Phase Additives

148

(1)

β-Cyclodextrin

149

(10)

Derivatized CDs

159

(1)

Macrocyclic Antibiotics

159

(1)

Chiral Counterions in Mobile Phase

160

(1)

Proteins as Mobile Phase Additives

161

(12)

General

161

(1)

Bovine Serum Albumin as a Mobile Phase Additive

162

(5)

Acknowledgments

167

(1)

References

168

(5)

An Overview of the Chiral Separation Mechanisms

173

(24)

Antoine-Michel Siouffi

Patrick Piras

Introduction

173

(2)

The Binding Sites: The Three-Point Chiral Recognition Model

175

(4)

Complexation Constants and Retention

179

(3)

Chiral Selector Immobilized on the Solid Phase Support

179

(2)

Chiral Selector in the Mobile Phase

181

(1)

Stoichiometry of Complexation

182

(1)

Enantiomeric Separation in Planar Chromatography

183

(8)

Ligand Exchange

183

(1)

Supramolecular and Inclusion Mechanisms

184

(1)

Cyclodextrins

184

(3)

Polysaccharides

187

(2)

Proteins

189

(1)

Molecular Imprinted Polymers

189

(2)

Conclusion

191

(6)

References

191

(6)

Separation of Diastereoisomers by Means of TLC

197

(34)

Virginia Coman

Introduction

197

(1)

Diastereoisomers

198

(1)

Nonchiral TLC Systems Used for Diastereoisomer Separation

199

(21)

Influence of Configuration

204

(9)

Influence of Conformation

213

(7)

Optimization of Diastereoisomer Separation by Derivatization

220

(3)

Overview on Diastereoisomer Separation by TLC

223

(4)

Conclusions

227

(4)

References

228

(3)

Selected Bottlenecks of Densitometric Detection with Chiral Analytes

231

(24)

Mieczyslaw Sajewicz

Teresa Kowalska

Introduction

231

(1)

2-Arylpropionic Acids and Their Spontaneous Oscillatory Transenantiomerization

232

(18)

Tracing of Oscillatory Transenantiomerization with the Selected APAs by Means of TLC

232

(7)

Two-Dimensional Retention of the Selected APAs on Chiral Stationary Phase in the ID Development Run

239

(5)

Oscillatory Changes in the UV Absorption Spectra and Their Impact on Densitometric Quantification of the Selected APAs

244

(1)

Oscillatory Changes in the UV Absorption Spectra of the Selected APAs

245

(2)

The Impact of the Oscillatory Changes in the UV Absorption Spectra on Densitometric Detection of the Selected APAs

247

(3)

Two-Dimensional Retention of the Selected APAs on Silica Gel in the 1D Development Run as Evidence of Its Chirality

250

(5)

References

253

(2)

Chirality of Pharmaceutical Products

255

(28)

Jan Krzek

Jacek Bojarski

Irma Podolak

Ewa Leciejewicz-Ziemecka

Introduction

255

(2)

Structure, Forms, and Physicochemical Properties of Chiral Drugs

257

(2)

Methods of Determination of Enantiomers

259

(3)

Qualitative Analysis

260

(1)

Quantitative Analysis

261

(1)

Purity of Chiral Stereomers

262

(1)

Pharmacodynamic and Pharmacokinetic Aspects of Chiral Drugs

263

(2)

Pharmacodynamic Differences among Stereoisomers of Selected Chiral Drags

265

(18)

Single Stereoisomers

265

(1)

Stereoisomer Mixtures

266

(2)

Stereomers of Natural Origin

268

(2)

Selected single compounds

270

(5)

Selected classes of compounds

275

(3)

References

278

(5)

Chiral Separation of β-Adrenergic Antagonists

283

(22)

Danica Agbaba

Branka Ivkovic

Introduction

283

(3)

Direct Separation of β-Blockers

286

(12)

Separation on the Chiral Stationary Phases

286

(1)

Molecular Imprinted Polymers (MIPs)

286

(3)

Triphenylcarbamate Derivatives of Cellulose asCSP

289

(1)

Separation on the Plates Impregnated with Pure Chiral Compounds

290

(1)

Separation on the Plates Impregnated with Chiral Selectors Preceded by Chemical Derivatization of the Selected β-Blockers

290

(1)

Separation on the Plates Impregnated with Chiral Selector

291

(4)

Separation Using Mobile Phase Additives (CMPAs)

295

(2)

Separation Using Counter-Ions as CMPA

297

(1)

Indirect Separation of β-Blockers

298

(7)

References

302

(3)

Chiral Separation of Amino Acid Enantiomers

305

(18)

Wtadystaw Golkiewicz

Beata Polak

Introduction

305

(1)

Separation of Amino Acid Enantiomers on the Commercial Chiral Plates

306

(5)

Separation of Amino Acid Enantiomers on the Impregnated Plates with Chiral Reagent

311

(3)

Separation of Amino Acid Enantiomers on the Commercial Plates with Chiral Reagent in Mobile Phase

314

(3)

Most Popular Chiral Reagents Used for Derivatization of Amino Acid Enantiomers

317

(3)

Conclusions

320

(3)

References

320

(3)

Chiral Separation of Nonsteroidal Anti-Inflammatory Drugs

323

(34)

Ravi Bhushan

Jurgen Martens

Introduction

324

(7)

General Structure and Properties of NSAIDs

324

(1)

Classification of NSAIDs

325

(1)

Salicylates

325

(1)

Propionic Acid Derivatives (Profens)

325

(1)

Aryl and Heteroarylacetic Acids

326

(1)

Anthranilates

326

(3)

Oxicams (Enolic Acids)

329

(1)

Phenylpyrazolones

330

(1)

Anilides

330

(1)

Approach to Enantioseparation

331

(1)

Chromatographic Methods of Separation

331

(1)

Thin-Layer Chromatography

332

(21)

Advantages of TLC

332

(1)

Impregnated TLC

332

(1)

Methods for Impregnation

333

(1)

Separation Mechanism

333

(1)

Role of Impregnation

333

(1)

Ligand Exchange

334

(1)

Inclusion Complex (Guest-Host Steric Interaction)

334

(1)

Preparation of Plates Impregnated with Chiral Selector

335

(1)

Applications (TLC Resolution of Enantiomers)

336

(1)

Ibuprofen

336

(7)

Flurbiprofen

343

(1)

Other NSAIDs

344

(2)

Effect of Temperature, pH, and Concentration of Chiral Selector

346

(2)

Detection Using Impregnation

348

(3)

Investigation of Oscillatory Instability of Enantiomers

351

(2)

Conclusion

353

(4)

Acknowledgments

353

(1)

References

353

(4)

Determination of Components in Selected Chiral Drugs

357

(26)

Jan Krzek

Irma Podolak

Urszula Hubicka

Anna Kwiecien

Introduction

358

(1)

Synthetic Drugs

359

(13)

Quinolones

359

(1)

Ofloxacin

359

(1)

1,4-Dihydropyridine Derivatives

360

(1)

Felodipine

360

(1)

Nimodipine

361

(1)

Aryloxypropanolamine Derivatives

362

(1)

Isoprenaline

362

(1)

Carvedilol

362

(1)

Metoprolol

363

(2)

Propranolol

365

(2)

Oxprenolol

367

(1)

Atenolol

367

(1)

Alprenolol

368

(1)

Phenothiazine Derivatives

368

(1)

Promethazine

368

(1)

Glucocorticosteroids

369

(1)

Budesonide

369

(1)

Others

370

(1)

Penicillamine

370

(1)

Ascorbic Acid and Dehydroascorbic Acid

371

(1)

Drugs of Natural Origin

372

(11)

Planar Separations of Chiral Natural Compounds

372

(1)

Flavonoids

373

(3)

Alkaloids

376

(1)

Quinine

376

(1)

Hyoscyamine

377

(1)

Ephedrine

378

(1)

Fatty Acids

379

(1)

References

379

(4)

Chiral Separations Using Marfey's Reagent

383

(26)

Ravi Bhushan

Hans Bruckner

Introduction

383

(1)

Resolution of Enantiomers (or Diastereomers)

384

(1)

Marfey's Reagent

385

(5)

General Protocols for Synthesis

386

(1)

Synthesis of FDNP-L-Ala-NH2

386

(2)

Synthesis of L-and D-diastereomers of amino acids

388

(1)

Detection

389

(1)

Advantages

389

(1)

Disadvantages

390

(1)

Chiral Variants and Structural Analogs of MR

390

(2)

Mechanism for Resolution of Diastereomers

392

(4)

Hydrogen Bonding

392

(1)

Conformation

393

(2)

Difference in the Hydrophobicity

395

(1)

TLC Applications of Marfey's Reagent

396

(8)

Enantiomeric Resolution via FDAA Diastereomers

396

(2)

Separation of FDAA Derivatives by 2D TLC

398

(3)

Resolution of FDPA Derivatives of Proteinaceous Amino Acids by Normal and RP TLC

401

(1)

Resolution of Certain Nonproteinaceous Amino Acids by Normal and RP TLC

402

(2)

Conclusion

404

(5)

Acknowledgments

405

(1)

References

405

(4)

Index

409

Kowalska, Teresa; Sherma, Joseph

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E-grāmata: Thin Layer Chromatography in Chiral Separations and Analysis

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