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E-grāmata: Synthesis and Characterization of Glycosides

Marco Brito-Arias

Formāts: PDF+DRM
Izdošanas datums: 03-Jun-2016
Izdevniecība: Springer International Publishing AG
Valoda: eng
ISBN-13: 9783319323107

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Formāts: PDF+DRM
Izdošanas datums: 03-Jun-2016
Izdevniecība: Springer International Publishing AG
Valoda: eng
ISBN-13: 9783319323107

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This second edition is a short and comprehensive study on the best known approaches for preparing the main types of glycosides. It covers synthetic pathways of challenging glycosides known as antiviral or antineoplastic drugs, and synthetic substrates used for enzymatic detection, including those used for detection of gene markers in plant biotechnology. The author pays special attention to the structural characterization of glycosides and provides the basic tools for the structural assignment through NMR, X-Ray and mass spectra techniques. The book also covers strategies for preparation of antiviral and antineoplastic drugs included in a drug design course.

Introduction.- O-Glycoside Formation.- N-glycosides.- Nucleotide Mimetics.- C-glycosides.- Glycoconjugates.- Hydrolysis of Glycosides.- Nuclear Magnetic Resonance of Glycosides.- X-Ray Diffraction of Glycosides.- Mass Spectrometry of Glycosides.- Docking studies of Glycosides.- Index.

1 Glycosides, Synthesis and Characterization

(80)

1.1 Introduction

(1)

1.2 Reactions of Monosaccharides

(1)

1.3 Chemical Modifications

(10)

1.3.1 Oxidations

(5)

1.3.2 Periodate Oxidation

(1)

1.3.3 Tollens Reaction

(1)

1.3.4 Benedict and Fehling Test

(1)

1.3.5 Nucleophilic Addition

(1)

1.3.6 Enediol Rearrangement

(1)

1.3.7 Kiliani--Fischer Synthesis

(1)

1.3.8 Ruff Degradation

(1)

1.3.9 Amadori Rearrangement

(1)

1.3.10 Conversion to Furfural Derivatives

(1)

1.3.11 Preparation of 5-Hydroxymethylfurfural (HMF)

(1)

1.4 Biosynthesis of Sugars

(2)

1.4.1 Sugars as Energy Sources

(1)

1.5 Synthesis of Carbohydrates

(15)

1.5.1 Chemical Synthesis

(5)

1.5.2 C-glycosyl Amino Acids

(4)

1.5.3 Enzymatic Synthesis

(4)

1.5.4 Chemoenzymatic Synthesis

(1)

1.6 Synthesis of Carbohydrates Mimetics

(8)

1.6.1 Iminosugars

(1)

1.6.2 Amino Sugars

(3)

1.6.3 Thiopyranoside Monosaccharides

(2)

1.6.4 Carbapyranoside-Saccharides

(2)

1.7 Glycoside Reactivity

(1)

1.8 The Leaving Groups

(1)

1.9 Glycosyl Donors

(7)

1.9.1 Glycosyl Halides

(6)

1.9.2 Glycosyl Donor Interconversion

(1)

1.10 Protecting Groups

(9)

1.11 Selective Protections (Scheme 1.86)

(8)

1.12 Selective Deprotections (Table 1.5, Scheme 1.87)

(18)

References

(10)

2 O-glycoside Formation

(88)

2.1 General Methods

(88)

2.1.1 Michael Reaction

(2)

2.1.2 Fischer Reaction

(2)

2.1.3 Koenigs--Knorr Reaction

(6)

2.1.4 Helferich Reaction

(3)

2.1.5 Acetate Donors

(2)

2.1.6 Imidate Reaction

(10)

2.1.7 Sulfur Reaction

107

(8)

2.1.8 Unprotected Glycosylations

115

(2)

2.1.9 Armed--Disarmed Method

117

(4)

2.1.10 Glycal Reaction

121

(6)

2.1.11 Fluorine Reaction

127

(3)

2.1.12 Iodine Reaction

130

(3)

2.1.13 Silyl Reaction

133

(1)

2.1.14 Phosphate Reaction

134

(1)

2.1.15 Pool Strategy

134

(1)

2.1.16 Enzymatic Approach

135

(7)

2.1.17 Solid Phase Methodology

142

(6)

2.1.18 Miscellaneous Glycosylations

148

(5)

2.1.19 Cyclic Oligosaccharides

153

(8)

References

161

(8)

3 N-glycosides

169

(46)

3.1 Nucleoside Formation

170

(1)

3.2 Protecting Groups

171

(12)

3.2.1 Ribofuranoside Protecting Groups

174

(9)

3.3 General Methods

183

(18)

3.3.1 Michael Reaction

183

(2)

3.3.2 Fischer--Helferich Reaction

185

(3)

3.3.3 The Davol--Lowy Reaction

188

(2)

3.3.4 Silyl Coupling Reaction

190

(5)

3.3.5 Sulfur Mediated Reaction

195

(1)

3.3.6 Imidate Mediated Reaction

196

(1)

3.3.7 Mitsunobu Reaction

196

(1)

3.3.8 Palladium Mediated Reaction

197

(1)

3.3.9 Ortho--alkynylbenzoates Protocol

198

(1)

3.3.10 Microbial/Enzymatic Approach

199

(2)

3.4 Oligonucleotide Synthesis

201

(14)

3.4.1 Phosphoramidite Method

203

(1)

3.4.2 HOBt Solid Phase Synthesis

204

(1)

3.4.3 Phosphonate Method

205

(1)

3.4.4 Phosphorimidazolides Method

206

(1)

3.4.5 Modified Oligonucleotides

206

(5)

References

211

(4)

4 Nucleoside Mimetics

215

(66)

4.1 Modified N-nucleosides

216

(21)

4.1.1 Heterocycle Modifications

218

(4)

4.1.2 Sugar Modifications

222

(12)

4.1.3 Complex Nucleosides

234

(3)

4.2 C-nucleosides

237

(9)

4.3 Carbocyclic Nucleosides

246

(15)

4.3.1 Cyclopropane Carbocyclic Nucleosides

251

(1)

4.3.2 Cyclobutane Carbocyclic Nucleosides

251

(1)

4.3.3 Cyclopentane Carbocyclic Nucleosides

252

(1)

4.3.4 Palladium Mediated

253

(4)

4.3.5 Enzymatic Synthesis

257

(2)

4.3.6 Carbocyclic C-nucleosides

259

(2)

4.4 Acyclic Nucleosides

261

(4)

4.5 Thionucleosides

265

(16)

4.5.1 Preparation of Thioribofuranosyl Intermediates

267

(1)

4.5.2 Glycosidic Bond Formation

268

(4)

References

272

(9)

5 C-glycosides

281

(30)

5.1 Synthetic Approaches for the Preparation of C-Glycosides

282

(29)

5.1.1 Electrophilic Glycosyl Donors

286

(4)

5.1.2 Concerted Reaction and Ring Formation

290

(1)

5.1.3 Palladium Mediated Reactions

291

(4)

5.1.4 Mitsunobu Reaction

295

(1)

5.1.5 Nucleophilic Sugars

295

(3)

5.1.6 Cross-Metathesis Reaction

298

(1)

5.1.7 Samarium Promoted Reaction

298

(1)

5.1.8 The Ramberg--Backlund Reaction

299

(1)

5.1.9 Free Radical Approach

300

(1)

5.1.10 Exoglycals

300

(4)

5.1.11 The Tether Approach

304

(1)

5.1.12 Unprotected Sugars

304

(2)

References

306

(5)

6 Glycoconjugates

311

(44)

6.1 Biological Function and Structural Information

311

(5)

6.1.1 Classification of Glycocoproteins

312

(2)

6.1.2 Recognition Sites

314

(1)

6.1.3 Structural information of Glycoproteins

314

(2)

6.2 Carbohydrate-Binding Proteins

316

(3)

6.2.1 Combining Sites

317

(2)

6.3 Glycopeptide Synthesis

319

(5)

6.4 Glycoprotein Synthesis

324

(9)

6.4.1 Indiscriminate Glycosylation

325

(1)

6.4.2 Chemoselective and Site-Specific Glycosylation

325

(1)

6.4.3 Site-Selective Glycosylation

325

(1)

6.4.4 Lansbury Aspartylation

325

(6)

6.4.5 Guanylation Reaction

331

(1)

6.4.6 Enzymatic Synthesis

332

(1)

6.5 Synthesis of Antigenic Glycoconjugates

333

(9)

6.5.1 Glycosphingolipid and Gangliosides

333

(9)

6.6 Glycopeptoids

342

(2)

6.7 Synthetic Vaccines

344

(11)

References

348

(7)

7 Hydrolysis of Glycosides

355

(14)

7.1 Acidic Hydrolysis

355

(2)

7.2 Basic Hydrolysis

357

(2)

7.2.1 Phenolic Glycosides

357

(1)

7.2.2 Enolic Glycosides

357

(1)

7.2.3 β-substituted Alcohol Glycosides

357

(2)

7.3 Enzymatic Hydrolysis

359

(10)

7.3.1 β-glucosidases

359

(1)

7.3.2 β-glucanases, β-chitinases

359

(1)

7.3.3 β-cellulase

359

(1)

7.3.4 β-glucuronidase

360

(1)

7.3.5 Glycosidase Enzymatic Activity Detection

360

(1)

7.3.6 β-1,4-glucanases

361

(1)

7.3.7 Fluorescent O-Glycosides

361

(1)

7.3.8 O-glycosides Measured by Absorption

362

(1)

7.3.9 Histochemical O-Glycosides

362

(4)

References

366

(3)

8 Nuclear Magnetic Resonance of Glycosides

369

(22)

8.1 NMR of Glycosides

369

(15)

8.2 NMR of N-glycosides

384

(7)

References

386

(5)

9 X-Ray Diffraction of Glycosides

391

(14)

9.1 X-ray Diffraction of O-Glycosides

393

(1)

9.2 X-ray Diffraction of Nucleosides

394

(11)

References

402

(3)

10 Mass Spectrometry of Glycosides

405

(12)

10.1 FAB Fragmentation Patters

407

(6)

10.2 The Domon--Costello Fragmentation

413

(4)

References

415

(2)

Index

417

Marco Brito-Arias is at the National Polytechnic Institute in Mexico.

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E-grāmata: Synthesis and Characterization of Glycosides

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