The organic chemistry of sugars
Навигация

Выставка новых поступлений  |  Поступления иностранных книг в библиотеки СО РАН : 2003 | 2006 |2008
 
Книжные оглавления
The organic chemistry of sugars / ed. by Levy D.E., Fugedi P. - Boca Raton: CRC/Taylor & Francis, 2006. - 880 p. - ISBN 0-8247-5355-0.
 
ОглавлениеСноска

Foreword ...................................................................... vii
Preface ........................................................................ ix
Contributors ................................................................. xiii

Part I
A Discussion of Carbohydrate Chemistry

Chapter 1 An Historical Overview ................................................ 3
Robert J. Ferrier
1.1 Introduction ................................................................ 3
1.2 The Beginnings .............................................................. 4
1.3 The Era of Emil Fischer ..................................................... 5
1.4 The Post-Fischer Era ........................................................ 8
1.5 New Methods: New Thinking .................................................. 11
1.6 New Horizons: Glycobiology ................................................. 15
1.7 The Beginning of the 21st Century .......................................... 19
1.8 Postscript ................................................................. 20
Acknowledgments ................................................................ 22
References ..................................................................... 22

Chapter 2 Introduction to Carbohydrates ........................................ 25
Janos Kuszmann
2.1 Definitions and Conventions ................................................ 25
2.2 Acyclic Derivatives ........................................................ 26
    2.2.1  Rules of the Fischer Projection ..................................... 26
    2.2.2  Trivial and Systematic Names ........................................ 28
    2.2.3  Absolute and Relative Configuration ................................. 31
    2.2.4  Depiction of the Conformation of Open Chain Carbohydrates ........... 31
    2.2.5  The Newman Projection ............................................... 33
2.3 Cyclic Derivatives ......................................................... 34
    2.3.1  Rules of the Fischer Projection ..................................... 34
    2.3.2  Mutarotation ........................................................ 35
    2.3.3  The Haworth Projection .............................................. 36
    2.3.4  The Mills Projection ................................................ 37
    2.3.5  The Reeves Projection ............................................... 37
    2.3.6  Conformations of the Six-Membered Rings ............................. 39
    2.3.7  Conformations of the Five-Membered Rings ............................ 40
    2.3.8  Conformations of the Seven-Membered Rings ........................... 40
    2.3.9  Conformations of Fused Rings ........................................ 41
    2.3.10 Steric Factors ...................................................... 43
    2.3.11 The Anomeric and Exo-Anomeric Effects ............................... 45
2.4 Definition and Nomenclature of Di- and Oligosaccharides .................... 47
    2.4.1  Disaccharides ....................................................... 47
    2.4.2  Oligosaccharides .................................................... 50
Further Reading ................................................................ 52

Chapter 3 Protective Group Strategies .......................................... 53
Stefan Oscarson
3.1 Introduction ............................................................... 54
3.2 Protecting Groups .......................................................... 54
    3.2.1 Hydroxyl Protecting Groups ........................................... 54
    3.2.2 Anomeric (Hemiacetal) Protecting Groups .............................. 60
    3.2.3 Amino Protecting Groups .............................................. 61
    3.2.4 Carboxyl Protecting Groups ........................................... 63
3.3 Selective Protection Methodologies (Regioselective Protection of Hydroxyl
    Groups)..................................................................... 64
    3.3.1 Selective Protection ................................................. 64
    3.3.2 Selective Deprotection ............................................... 70
3.4 Selective Protection Strategies ............................................ 72
    3.4.1 Monosaccharides ...................................................... 72
    3.4.2 Disaccharides ........................................................ 75
    3.4.3 Oligosaccharides ..................................................... 80
3.5 Summary and Conclusions .................................................... 84
References ..................................................................... 85

Chapter 4 Glycosylation Methods ................................................ 89
Peter Fugedi
4.1 Introduction ............................................................... 90
4.2 Stereochemical Aspects of Glycoside Bond Formation ......................... 91
4.3 Glycosylations by Nucleophilic Substitutions at the Anomeric Carbon ........ 96
    4.3.1 Synthesis of Glycosides from Glycosyl Halides ........................ 96
    4.3.2 Synthesis of Glycosides from Anomeric Thio Derivatives .............. 102
    4.3.3 Synthesis of Glycosides from Anomeric O-Derivatives ................. 113
    4.3.4 Synthesis of Glycosides from Donors with Other Heteroatoms
          at the Anomeric Center .............................................. 142
4.4 Glycosylations by Nucleophilic Substitution at the Aglycone Carbon ........ 144
4.5 Synthesis of Glycosides by Addition Reactions ............................. 146
4.6 Other Glycosylation Methods ............................................... 149
4.7 Summary and Outlook ....................................................... 150
References .................................................................... 151

Chapter 5 Oligosaccharide Synthesis ........................................... 181
Peter Fugedi
5.1 Introduction .............................................................. 181
5.2 General Concept of Oligosaccharide Synthesis .............................. 182
5.3 Stepwise and Block Syntheses of Oligosaccharides .......................... 183
5.4 Glycosylation Strategies in Block Syntheses ............................... 190
    5.4.1 Reactivation by Exchange of the Anomeric Substituent ................ 190
    5.4.2 Sequential Glycosylations with Different Types of Glycosyl
          Donors .............................................................. 190
    5.4.3 Two-Stage Activation ................................................ 193
    5.4.4 Orthogonal Glycosylations ........................................... 194
    5.4.5 Armed-Disarmed Glycosylations ....................................... 196
    5.4.6 Active-Latent Glycosylations ........................................ 197
5.5 Methods and Techniques in Oligosaccharide Synthesis ....................... 202
    5.5.1 Intramolecular Aglycone Delivery .................................... 202
    5.5.2 One-Pot Multistep Glycosylations .................................... 204
    5.5.3 Polymer-Supported and Solid-Phase Oligosaccharide Synthesis ......... 208
5.6 Summary and Outlook ....................................................... 214
References .................................................................... 216

Part II
From Sugars to Sugar-Like Structures to Non-Sugars

Chapter 6 Functionalization of Sugars ......................................... 225
Daniel E. Levy
6.1  Introduction ............................................................. 226
     6.1.1 Definition of Concept .............................................. 226
     6.1.2 SN2 Reactions ...................................................... 227
6.2  Special Considerations with Sugars ....................................... 227
     6.2.1 Axial vs. Equatorial Approach ...................................... 228
     6.2.2 Substitution vs. Elimination ....................................... 228
     6.2.3 Neighboring Group Participation .................................... 229
6.3  Formation of Leaving Groups .............................................. 231
     6.3.1 Halides as Leaving Groups .......................................... 232
     6.3.2 Sulfonates as Leaving Groups ....................................... 232
     6.3.3 Epoxysugars (Anhydro Sugars) ....................................... 232
     6.3.4 Other Leaving Groups (Mitsunobu Reaction, Chlorosulfate Esters,
           Cyclic Sulfates) ................................................... 233
6.4  Halogenation Reactions ................................................... 235
     6.4.1 SN2 Displacements of Sulfonates .................................... 235
     6.4.2 SN2 Opening of Epoxides ............................................ 236
     6.4.3 Use of Alkylphosphonium Salts ...................................... 237
     6.4.4 Use of Chlorosulfate Esters ........................................ 238
     6.4.5 Use of Iminoesters and Sulfonylchlorides ........................... 238
     6.4.6 Fluorination Reactions ............................................. 239
     6.4.7 Halogenation of O-Benzylidene Acetals .............................. 239
     6.4.8 Radical Processes .................................................. 241
6.5  Reactions Involving Nitrogen ............................................. 241
     6.5.1 SN2 Reactions ...................................................... 241
     6.5.2 Formation of Nitrosugars ........................................... 243
     6.5.3 The Mitsunobu Reaction ............................................. 243
6.6  Reactions Involving Oxygen and Sulfur .................................... 244
     6.6.1 Manipulation of Sugar Hydroxyl Groups .............................. 244
     6.6.2 Deoxygenation Reactions ............................................ 245
     6.6.3 Sulfuration Reactions .............................................. 249
     6.6.4 Desulfuration Reactions ............................................ 250
6.7  Formation of Carbon-Carbon Bonds ......................................... 251
     6.7.1 Addition of Nucleophiles ........................................... 251
     6.7.2 Condensation Reactions ............................................. 254
     6.7.3 Wittig/Horner-Emmons Reactions ..................................... 256
     6.7.4 Claisen Rearrangements ............................................. 256
6.8  Reductions and Oxidations ................................................ 257
     6.8.1 Reduction Reactions ................................................ 257
     6.8.2 Oxidation Reactions ................................................ 260
6.9  Rearrangements and Isomerizations ........................................ 261
     6.9.1 Base Catalyzed Isomerizations ...................................... 261
     6.9.2 The Amadori Rearrangement .......................................... 261
6.10 Conclusion ............................................................... 263
References .................................................................... 263

Chapter 7 Strategies towards C-Glycosides ..................................... 269
Daniel E. Levy
7.1 Introduction .............................................................. 271
    7.1.1  Definition and Nomenclature of C-Glycosides ........................ 271
    7.1.2  O-Glycosides vs. C-Glycosides: Comparisons of Physical
           Properties, Anomeric Effects, H-Bonding Abilities, Stabilities
           and Conformations .................................................. 271
    7.1.3  Natural Occurring C-Glycosides ..................................... 273
    7.1.4  C-Glycosides as Stable Pharmacophores .............................. 273
7.2 Synthesis of C-Glycosides via Electrophilic Substitutions ................. 274
    7.2.1  Anomeric Activating Groups and Stereoselectivity ................... 275
    7.2.2  Cyanation Reactions ................................................ 275
    7.2.3  Alkylation, Allenylation, Allylation and Alkynation Reactions ...... 278
    7.2.4  Arylation Reactions ................................................ 286
    7.2.5  Reactions with Enol Ethers, Silylenol Ethers and Enamines .......... 291
    7.2.6  Nitroalkylation Reactions .......................................... 294
    7.2.7  Reactions with Allylic Ethers ...................................... 295
    7.2.8  Wittig Reactions with Lactols ...................................... 297
    7.2.9  Nucleophilic Additions to Sugar Lactones Followed by Lactol
           Reductions ......................................................... 299
    7.2.10 Nucleophilic Additions to Sugars Containing Enones ................. 302
    7.2.11 Transition Metal-Mediated Carbon Monoxide Insertions ............... 304
    7.2.12 Reactions Involving Anomeric Carbenes .............................. 305
    7.2.13 Reactions Involving Exoanomeric Methylenes ......................... 305
7.3 Synthesis of C-Glycosides via Nucleophilic Sugar Substitutions ............ 307
    7.3.1  C-1 Lithiated Anomeric Carbanions by Direct Metal Exchange ......... 307
    7.3.2  C-1 Lithiated Anomeric Carbanions by Reduction ..................... 310
    7.3.3  C-1 Carbanions Stabilized by Sulfones, Sulfoxides,
           Carboxyl and Nitro Groups .......................................... 311
7.4 Synthesis of C-Glycosides via Transition Metal-Based Methodologies ........ 314
    7.4.1  Direct Coupling of Glycals with Aryl Groups ........................ 315
    7.4.2  Coupling of Substituted Glycals with Aryl Groups ................... 316
    7.4.3  Coupling of π-Allyl Complexes of Glycals ........................... 317
7.5 Synthesis of C-Glycosides via Anomeric Radicals ........................... 319
    7.5.1  Sources of Anomeric Radicals and Stereochemical Consequences ....... 319
    7.5.2  Anomeric Couplings with Radical Acceptors .......................... 320
    7.5.3  Intramolecular Radical Reactions ................................... 322
7.6 Synthesis of C-Glycosides via Rearrangements and Cycloadditions ........... 324
    7.6.1  Rearrangements by Substituent Cleavage and Recombination ........... 324
    7.6.2  Electrocyclic Rearrangements Involving Glycals ..................... 326
    7.6.3  Rearrangements from the 2-Hydroxyl Group ........................... 326
7.7 Synthesis of C-Glycosides via Formation of the Sugar Ring ................. 327
    7.7.1  Wittig Reactions of Lactols Followed by Ring Closures .............. 329
    7.7.2  Addition of Grignard and Organozinc Reagents to Lactols ............ 331
    7.7.3  Cyclization of Suitably Substituted Polyols ........................ 331
    7.7.4  Rearrangements ..................................................... 333
    7.7.5  Cycloadditions ..................................................... 335
    7.7.6  Other Methods for the Formation of Sugar Rings ..................... 336
7.8 Further Reading ........................................................... 336
Acknowledgments ............................................................... 337
References .................................................................... 337

Chapter 8 From sugars to carba-sugars ......................................... 349
Matthieu Sollogoub, Pierre Sinay
8.1 Introduction .............................................................. 349
8.2 Why Synthesize Carba-Sugars? .............................................. 350
    8.2.1 Carba-Monosaccharides ............................................... 350
    8.2.2 Carba-Oligosaccharides .............................................. 352
    8.2.3 Carba-Glycosyl-Phosphates ........................................... 353
8.3 Synthesis of Carba-Sugars from Sugars ..................................... 355
    8.3.1 Cyclization of Open-Chain Sugars .................................... 355
    8.3.2 Rearrangements of Cyclic Sugars ..................................... 371
8.4 Conclusion ................................................................ 378
References .................................................................... 378

Chapter 9 Sugars with endocyclic heteroatoms other than oxygen ................ 383
Peter Greimel, Josef Spreitz, Frederich K. (Fitz) Sprenger, Arnold E. Stutz,
Tanja M. Wrodnigg
9.1 Introduction .............................................................. 384
9.2 Thiosugars with Sulfur in the Ring ........................................ 385
    9.2.1 Furanoid Systems .................................................... 386
    9.2.2 Pyranoid Systems --- 5-Thioaldohexoses, 6-Thioketohexoses
          and Derivatives ..................................................... 388
    9.2.3 Septanoses and Derivatives .......................................... 390
    9.2.4 Examples of Glycomimetics with Sulfur in the Ring ................... 390
9.3 Iminosugars ............................................................... 395
    9.3.1 Typical Approaches to Iminosugars and Analogs ....................... 396
    9.3.2 Biological Activities and Applications .............................. 401
9.4 Other Heteroatoms in the Ring ............................................. 411
9.5 Further Reading ........................................................... 412
References .................................................................... 412

Part III
Sugars as Tools, Chiral Pool Starting Materials and Formidable Synthetic Targets

Chapter 10 Sugars as chiral auxiliaries ....................................... 427
Norbert Pleuss, Gernot Zech, Bartlomiej Furman, Horst Kunz
10.1 Introduction ............................................................. 427
10.2 Asymmetric Cycloaddition Reactions ....................................... 428
     10.2.1 [2+1] Cycloadditions .............................................. 428
     10.2.2 [2+2] Cycloadditions .............................................. 429
     10.2.3 [3+2] Cycloadditions .............................................. 435
     10.2.4 [4+2] Cycloadditions (Diels--Alder Reactions) ..................... 439
     10.2.5 Hetero Diels--Alder Reactions ..................................... 448
10.3 Stereoselective Addition and Substitution Reactions ...................... 454
     10.3.1 Additions to Glycosyl Imines and Other Nucleophilic Additions ..... 454
     10.3.2 Conjugate Additions ............................................... 460
     10.3.3 Reactions Involving Enolates ...................................... 466
10.4 Rearrangement Reactions .................................................. 472
10.5 Radical Reactions ........................................................ 475
10.6 Miscellaneous Applications of Carbohydrate Auxiliaries ................... 478
10.7 Conclusion ............................................................... 480
References .................................................................... 481

Chapter 11 Sugars as Chiral Starting Materials in Enantiospecific Synthesis ... 489
Yves Chapleur and Francoise Chretien
11.1 Introduction ............................................................. 490
11.2 Carbohydrates as Sources of Carbon Atoms in Total Syntheses .............. 491
11.3 Branching a Carbon Chain on the Carbohydrate Ring ........................ 492
     11.3.1 Using Epoxides .................................................... 492
     11.3.2 Using Unsaturated Carbohydrates ................................... 496
     11.3.3 Using Keto-Sugars ................................................. 501
     11.3.4 Using Carbohydrates as Nucleophiles ............................... 511
     11.3.5 Using Rearrangements .............................................. 516
11.4 Chain Extensions of Sugars ............................................... 520
     11.4.1 Chain Extensions at the Primary Carbon Atom ....................... 521
     11.4.2 Chain Extensions at the Anomeric Center ........................... 532
11.5 Creation of C-Glycosidic Bonds ........................................... 534
     11.5.1 Creation of C-Glycosidic Bonds with Retention
            of the Anomeric Hydroxyl Group .................................... 535
     11.5.2 Creation of C-Glycosidic Bonds with Replacement
            of the Anomeric Hydroxyl Group .................................... 537
11.6 Formation of Carbocycles ................................................. 545
     11.6.1 Carbocyclization of the Sugar Backbone ............................ 546
     11.6.2 Annulation Reactions on the Sugar Template ........................ 553
11.7 Conclusions .............................................................. 557
References .................................................................... 558

Chapter 12 Synthesis of Carbohydrate Containing Complex Natural Compounds ..... 575
Kazunobu Toshima
12.1 Introduction ............................................................. 576
12.2 O-Glycoside Antibiotics .................................................. 576
     12.2.1  Methymycin ....................................................... 576
     12.2.2  Erythromycin A ................................................... 577
     12.2.3  Tylosin .......................................................... 577
     12.2.4  Mycinamicins IV and VII .......................................... 578
     12.2.5  Avermectins ...................................................... 580
     12.2.6  Efrotomycin ...................................................... 582
     12.2.7  Amphotericin B ................................................... 583
     12.2.8  Elaiophylin ...................................................... 583
     12.2.9  Cytovaricin ...................................................... 584
     12.2.10 Calicheamicin γI1 ................................................ 587
     12.2.11 Neocarzinostatin Chromophore ..................................... 596
     12.2.12 Eleutherobin ..................................................... 596
     12.2.13 Olivomycin A ..................................................... 599
     12.2.14 Everninomicin 13,284-1 ........................................... 602
     12.2.15 Polycavernoside A ................................................ 604
     12.2.16 Vancomycin ....................................................... 606
     12.2.17 Apoptolidin ...................................................... 608
12.3 C-Glycoside Antibiotics .................................................. 611
     12.3.1  Vineomycinone B2 Methyl Ester .................................... 611
     12.3.2  Medermycin ....................................................... 614
     12.3.3  Urdamycinone B ................................................... 615
     12.3.4  Gilvocarcin M .................................................... 621
12.4 Others ................................................................... 621
     12.4.1  Bidesmosidic Triterpene Saponin .................................. 621
     12.4.2  Digitoxin ........................................................ 621
12.5  Concluding Remarks ...................................................... 621
References .................................................................... 624

Chapter 13 Total Asymmetric Synthesis of Monosaccharides and Analogs .......... 629
Pierre Vogel
13.1 Introduction ............................................................. 630
13.2 The Formose Reaction ..................................................... 631
13.3 Prebiotic Synthesis of Carbohydrates ..................................... 632
13.4 Aldolase-Catalyzed Asymmetric Aldol Condensations ........................ 634
     13.4.1 Resolution of Racemic Aldehydes ................................... 634
     13.4.2 One-Pot Total Syntheses of Carbohydrates .......................... 634
     13.4.3 Synthesis of 1,5-Dideoxy-1,5-Iminoalditols ........................ 638
     13.4.4 Synthesis of 2,5-Dideoxy-2,5-Iminoalditols ........................ 639
     13.4.5 Synthesis of Deoxy-Thiohexoses .................................... 641
13.5 Chain Elongation of Aldehydes through Nucleophilic Additions ............. 642
     13.5.1 Total Synthesis of D- and L-Glyceraldehyde and Other C-3
            Aldose Derivatives ................................................ 642
     13.5.2 One-Carbon Homologation of Aldoses: The Thiazole-Based Method ..... 645
     13.5.3 Other Methods of One-Carbon Chain Elongation of Aldoses ........... 647
     13.5.4 Additions of Enantiomerically Pure One-Carbon Synthons ............ 648
     13.5.5 Two-Carbon Chain Elongation of Aldehydes .......................... 648
     13.5.6 Three-Carbon Chain Elongations .................................... 665
     13.5.7 Four-Carbon Chain Elongations ..................................... 668
     13.5.8 Synthesis of Branched-Chain Monosaccharides from C3-Aldoses ....... 672
13.6 Hetero Diels-Alder Additions ............................................. 674
     13.6.1 Achiral Aldehydes as Dienophiles .................................. 674
     13.6.2 Chiral Aldehydes as Dienophiles: Synthesis of Long-Chain Sugars ... 675
     13.6.3 Hetero Diels-Alder Additions of 1-Oxa-1,3-dienes .................. 679
     13.6.4 Nitroso Dienophiles: Synthesis of Azasugars ....................... 681
     13.6.5 N-Methyltriazoline-3,5-Dione as a Dienophile:
            Synthesis of 1-Azafagomine ........................................ 682
13.7 Cycloadditions of Furans ................................................. 684
     13.7.1 Diels-Alder Additions ............................................. 684
     13.7.2 The "Naked Sugars of the First Generation" ........................ 685
     13.7.3 Dipolar Cycloadditions of Furans .................................. 694
     13.7.4 [4 + 3]-Cycloadditions of Furan ................................... 697
13.8 Carbohydrates and Analogs from Achiral Hydrocarbons ...................... 698
     13.8.1 From Cyclopentadiene .............................................. 698
     13.8.2 From Benzene and Derivatives ...................................... 701
     13.8.3 From Cycloheptatriene ............................................. 701
     13.8.4 From Penta-1,4-Diene .............................................. 703
13.9 Enantioselective Epoxidation of Allylic Alcohols ......................... 703
     13.9.1 Desymmetrization of meso Dienols .................................. 704
     13.9.2 Kinetic Resolution of Racemic Allylic Alcohols .................... 705
13.10 Enantioselective Sharpless Dihydroxylations and Aminohydroxylations ..... 707
13.11 Conclusion .............................................................. 710
References .................................................................... 710

Part IV
Additional Topics

Chapter 14 Combinatorial Carbohydrate Chemistry ............................... 729
Prabhat Arya and Bugga VNBS Sarma
14.1 Introduction ............................................................. 729
14.2 Solution-Phase Library Synthesis of Carbohydrates ........................ 731
     14.2.1 Hindsgaul's Random Glycosylation .................................. 731
     14.2.2 Boons's Latent-Active Glycosylation ............................... 731
     14.2.3 Ichikawa's Stereoselective (and Nonregioselective)
     Glycosylation ............................................................ 732
     14.2.4 Orthogonal Protection in Library Synthesis ........................ 733
14.3 Solid-Phase Library Synthesis of Carbohydrates ........................... 733
     14.3.1 Kahne's Split-Mix Approach to Glycosylation ....................... 734
     14.3.2 Boons's Two-Directional Approach .................................. 734
     14.3.3 Ito's Capture and Release Strategy ................................ 736
     14.3.4 Linkers in Solid-Phase Synthesis .................................. 737
14.4 Dynamic Combinatorial Chemistry .......................................... 738
14.5 Carbohydrate Scaffolds in Combinatorial Chemistry ........................ 739
14.6 Carbohydrate/Glycoconjugate-Like Compounds (Glycomimetics) by
     Combinatorial Chemistry .................................................. 741
     14.6.1 Multiple component condensations (MCC) ............................ 741
     14.6.2 Glycohybrids ...................................................... 742
14.7 Glycopeptide-like Derivatives by Combinatorial Chemistry ................. 743
     14.7.1 Glycosylated Amino Acids as Building Blocks ....................... 745
     14.7.2 Cyclic Artificial Glycopeptides ................................... 747
     14.7.3 Automated Synthesis of Artificial Glycopeptides ................... 747
14.8 Summary and Outlook ...................................................... 749
Acknowledgments ............................................................... 749
References .................................................................... 750

Chapter 15 Glycopeptides ...................................................... 755
Michael Mogemark and Jan Kihlberg
15.1 Structures and Biological Functions of Protein-Linked Carbohydrates ...... 755
15.2 General Aspects of Glycopeptide Synthesis ................................ 759
     15.2.1 Strategic Considerations .......................................... 759
     15.2.2 Selection of Protecting-Groups .................................... 759
     15.2.3 Practical Aspects of Solid-Phase Synthesis ........................ 762
15.3 Synthesis of O-Linked Glycopeptides ...................................... 764
     15.3.1 1,2-trans-O-Linked Glycopeptides .................................. 764
     15.3.2 1,2-cis-O-Linked Glycopeptides .................................... 771
15.4 Synthesis of N-Linked Glycopeptides ...................................... 781
15.5 Chemoenzymatic Synthesis of Glycopeptides ................................ 788
15.6 Synthesis of Glycoproteins ............................................... 792
References .................................................................... 792

Chapter 16 Carbohydrate Mimetics in Drug Discovery ............................ 803
Beat Ernst, Hartmuth C. Kolb and Oliver Schwardt
16.1 Introduction ............................................................. 804
16.2 MAG Antagonists .......................................................... 804
     16.2.1 Biological Rationale .............................................. 804
     16.2.2 The Siglec Family ................................................. 806
     16.2.3 MAG Antagonists ................................................... 807
     16.2.4 Summary of the Structure Affinity Relationship .................... 812
     16.2.5 Summary and Outlook ............................................... 814
16.3 Glycosidase Inhibitors ................................................... 814
     16.3.1 Biological Rationale .............................................. 814
     16.3.2 α-Glucosidase Inhibitors .......................................... 815
     16.3.3 Neuraminidase Inhibitors .......................................... 821
16.4 Selectin Antagonists ..................................................... 828
     16.4.1 Biological Rationale .............................................. 828
     16.4.2 Structure Affinity Relationship ................................... 831
     16.4.3 Families of Antagonists Identified So Far ......................... 833
     16.4.4 Biological Evaluation ............................................. 843
     16.4.5 Summary and Outlook ............................................... 844
Acknowledgments ............................................................... 845
References .................................................................... 845

Index ......................................................................... 863


Вверх The organic chemistry of sugars / ed. by Levy D.E., Fugedi P. - Boca Raton: CRC/Taylor & Francis, 2006. - 880 p. - ISBN 0-8247-5355-0.

Сигла: 063По алфавиту | По темам ||| Химия | Биология | Экология
[О библиотеке | Академгородок | Новости | Выставки | Ресурсы | Библиография | Партнеры | ИнфоЛоция | Поиск | English]
  Пожелания и письма: branch@gpntbsib.ru
© 1997-2020 Отделение ГПНТБ СО РАН (Новосибирск)
Статистика доступов: архив | текущая статистика
 

Документ изменен: Wed Feb 27 14:52:00 2019. Размер: 38,160 bytes.
Посещение N 1827 с 24.09.2007