Analytical Methods in Combinatorial Chemistry, Second Edition

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ISBN: 9780849318603 | 0849318602
Cover: Hardcover
Copyright: 8/9/2010

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Written by a leader in the field, Analytical Methods in Combinatorial Chemistry is the first comprehensive review of analytical methods in this field, with a focus on combinatorial drug discovery. The second edition updates the first with close to 50% new material and a detailed discussion of new developments in analytical methods, technologies, and applications in combinatorial chemistry in the past three years. The book also includes new chapters on high-throughput purification and the application of combinatorial chemistry in materials science and catalyst discovery. It focuses on new drug candidates and drugs developed through combinatorial chemistry.

Preface	p. xi
Authors	p. xiii
Analytical issues in combinatorial chemistry	p. 1
Combinatorial chemistry	p. 1
Synthesis methods	p. 3
Analytical challenges	p. 6
Properties of solid supports	p. 6
Reaction optimization stage	p. 6
Library synthesis stage	p. 7
Lead selection and optimization stage	p. 7
References	p. 8
An examination of the analytical sample: resin support	p. 13
Introduction	p. 13
Physical properties of resins	p. 14
Resin type	p. 14
Polystyrene resins	p. 14
PS-PEG resins	p. 15
Other resin and nonresin supports	p. 17
Resin bead size distribution	p. 17
Loading and the intraresin site distribution	p. 18
Thermal stability	p. 19
Chemical stability	p. 20
Resin swelling and solvation	p. 20
Effects of swelling on resin	p. 20
Effects of swelling on reagent and solvent molecules	p. 23
Swelling ability of solvents	p. 26
Dynamic resin solvation	p. 29
Effects of the solvated resin on solid-phase reactions	p. 33
The effects of support solvation on SPPS	p. 33
Resin support as another "solvent phase"	p. 35
Selective adsorption of reactant and reagent molecules	p. 35
The effect of phase-transfer catalyst (PTC) on SPOS reactions	p. 36
Support effects on SPOS reaction kinetics	p. 36
Site separation and site interaction	p. 38
Site-separation effect	p. 39
Site-interaction effect	p. 42
Factors affecting site separation	p. 45
Solid support effects on product purity	p. 48
Summary	p. 48
References	p. 49
Solid-phase reaction optimization using FTIR	p. 55
Introduction	p. 55
Comparison of FTIR and Raman techniques	p. 56
Techniques	p. 56
Analysis of resin-bound compounds	p. 61
Comparison of techniques	p. 64
Monitoring of polymer-supported organic reactions	p. 67
The monitoring of reactions on polystyrene-based resin	p. 69
Yes-and-no information	p. 69
Reaction kinetics on resin support	p. 72
Quantitative estimation of chemical conversions (%) on resin	p. 79
The selection of optimal reaction conditions using single-bead IR	p. 85
The monitoring of reactions on PS-PEG resins: Comparing the reaction rate on PS-PEG resins	p. 87
Background	p. 87
Examples	p. 88
Examples: Peptide secondary structure on resin support	p. 89
The monitoring of reactions on surface-functionalized polymers	p. 91
Techniques	p. 91
Examples	p. 93
Parallel reaction monitoring	p. 94
Summary	p. 95
References	p. 95
Reaction optimization using MS and NMR methods	p. 99
Introduction	p. 99
MS methods	p. 99
NMR methods	p. 101
Gel-phase NMR	p. 102
Gel-phase ¹³C NMR	p. 104
Gel-phase ¹⁹F NMR	p. 108
Gel-phase ³¹P NMR	p. 110
Gel-phase ¹⁵N NMR	p. 111
Gel-phase deuterium NMR	p. 112
Magic angle spinning (MAS) NMR	p. 113
1D NMR spectroscopy of resin samples	p. 114
2D NMR spectroscopy of resin samples	p. 118
NMR on multipin crowns	p. 122
Other NMR methods	p. 122
Flow NMR spectroscopy in drug discovery	p. 122
Flow injection analysis NMR (FIA-NMR)	p. 122
High-throughput NMR analysis using a multiple coil flow probe	p. 123
NMR detection with multiple solenoidal microcoils for continuous-flow capillary electrophoresis	p. 123
Quantitative measurements in continuous-flow HPLC/NMR	p. 124
Reaction monitoring in LPOS by ¹⁹F NMR	p. 124
Summary	p. 125
References	p. 126
Reaction optimization using spectrophotometric and other methods	p. 131
Introduction	p. 131
Qualitative analysis of amines	p. 132
Quantitative analysis of amines	p. 136
Quantitative spectroscopic methods for organic functional groups	p. 142
Quantitation of aldehyde/ketone groups	p. 142
Quantitation of hydroxyl groups on resin	p. 146
Quantitation of carboxyl groups on resin	p. 150
Quantitation of polymer-supported sulfhydryl groups	p. 151
Combustion elemental analysis methods	p. 152
Analysis of resin-bound organic compounds	p. 152
Quantitatively monitoring SPOS reactions	p. 153
Electrochemical methods	p. 156
On-resin X-ray, EPR, SERS, and fluorescence methods	p. 158
Summary	p. 159
References	p. 159
Quality control of combinatorial libraries	p. 163
Introduction	p. 163
Analysis of discrete compound libraries	p. 165
MS analysis	p. 165
MS-guided purification	p. 166
High-throughput NMR	p. 167
Analysis of pooled libraries	p. 169
Theoretical calculation of mass distribution	p. 169
MS analysis	p. 171
High-resolution MS	p. 175
Tandem MS	p. 177
Liquid chromatography (LC)/MS and capillary electrophoresis (CE)/MS	p. 180
LC-MS	p. 180
CE-MS	p. 181
NMR methods for mixture analysis	p. 184
HPLC for analyzing compounds from discrete and mixture libraries	p. 185
HPLC with a chemiluminescence nitrogen detector (CLND)	p. 186
Evaporative light scattering detector (ELSD)	p. 188
Summary	p. 189
References	p. 190
High-throughput purification	p. 195
Introduction	p. 195
Nonchromatographic high-throughput purification methods	p. 195
Chromatographic high-throughput purification methods	p. 197
Supercritical fluid chromatographic purification methods	p. 201
Purification methods based on fluorous chemistry separation technique	p. 206
Fluorous liquid-liquid extraction (F-LLE)	p. 207
Fluorous solid-phase extraction (F-SPE)	p. 207
Fluorous HPLC (F-HPLC)	p. 210
Fluorous-flash chromatography (F-FC)	p. 211
Summary	p. 212
References	p. 212
Final thoughts and future perspectives	p. 217
Introduction	p. 217
Stability of compound collections	p. 217
Nanocombinatorial library and associated analytical issues	p. 218
Green process and technologies	p. 218
References	p. 219
Index	p. 221
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