Handbook of Carbohydrate Engineering

dk3265fm.pdf......Page 1
HANDBOOK OF Carbohydrate Engineering......Page 2
Introduction......Page 4
I. ISOLATION, PURIFICATION, AND STRUCTURAL CHARACTERIZATION OF CARBOHYDRATES......Page 6
II. STUDY OF GLYCOSYLATION IN LIVING CELLS......Page 8
III. EXPLOITATION OF THE “GLYCOSYLATION MACHINERY” FOR THE PRODUCTION OF COMPLEX CARBOHYDRATES IN LIVING CELLS......Page 10
IV. CELL-FREE ENZYMATIC METHODS FOR CARBOHYDRATE SYNTHESIS......Page 11
V. CHEMICAL SYNTHETIC METHODS......Page 12
2. Creation of New Products from Abundant Polysaccharides......Page 13
1. Study of Human Disease and the Development of Diagnostic Tools......Page 14
1. Biosynthesis, Postsynthetic Processing, and Characterization......Page 15
1. Basic Building Blocks for the Assembly of Complex Carbohydrates......Page 16
REFERENCES......Page 17
Contributors......Page 23
Table of Contents......Page 32
I. INTRODUCTION — AN OVERVIEW OF MAMMALIAN GLYCOSYLATION......Page 35
Table of Contents......Page 0
A. CELLULAR INTAKE OF SUGARS......Page 37
B. INTRACELLULAR MONOSACCHARIDE PROCESSING......Page 45
D. GLYCOCONJUGATE BIOSYNTHESIS: GLYCOPROTEINS, GLYCOLIPIDS, AND POLYSACCHARIDES......Page 50
1. O-Linked Glycosylation......Page 51
a. Biosynthesis of the Complex Type Oligosaccharides......Page 53
3. Glycolipids......Page 55
4. GPI Membrane Anchors......Page 56
5. Polysaccharide Biosynthesis......Page 58
b. Heparan Sulfate and Heparin......Page 63
c. Chondroitin Sulfate......Page 64
E. POSTSYNTHETIC MODIFICATIONS FINE-TUNE CARBOHYDRATE STRUCTURE AND FUNCTION......Page 65
REFERENCES......Page 67
CONTENTS......Page 83
I. INTRODUCTION......Page 84
C. SIALIDASE TREATMENT......Page 85
G. GALα1-3GAL-BINDING ASSAY......Page 86
A. REVEALING α2-3-AND α2-6-LINKED SIALIC ACID ON MDCK AND VERO CELLS......Page 87
B. CARBOHYDRATE-BINDING PATTERN OF MDCK AND VERO CELLS......Page 88
C. PROBING OF VIRUSES WITH SUG-PAA-BIOT......Page 91
IV. DISCUSSION......Page 92
A. CARBOHYDRATE-BINDING PROPERTIES OF MDCK AND VERO CELLS......Page 93
B. PATTERN OF MDCK AND VERO CELLS SIALYLATION......Page 95
C. CARBOHYDRATE-BINDING PROPERTIES OF THE INFLUENZA VIRUS......Page 96
D. POSSIBLE INVOLVEMENT OF XENOANTIGENS......Page 97
REFERENCES......Page 99
CONTENTS......Page 104
I. INTRODUCTION......Page 105
A. INFLUENZA C-VIRUS......Page 106
B. ACHATININ-H......Page 108
C. CANCER ANTENNARIUS LECTIN......Page 109
1. Hemagglutination Assay......Page 110
2. Parasite Agglutination Assay......Page 111
4. Erythrocyte Binding Assay......Page 112
5. Quantitative Estimation of O-AcSG by Scatchard Plot......Page 113
6. Flow Cytometric Analysis......Page 115
a. Probe to Detect Anti-O-AcSG: Bovine Submaxillary Mucin (BSM)......Page 116
1. Quantitation of Sialic Acid and 9(8)-O-Acetyl Sialic Acid by the Acetyl Acetone Method......Page 118
3. Fluorimetric HPLC for Estimation of Sialic Acid (Neu5Ac) and Its Principal Derivatives......Page 119
4. Gas Chromatography/Mass Spectrometric Analysis of Sialic Acids as TMS–Methylester Derivatives......Page 120
A. 9-O-ACETYL SIALIC ACID AND COMPLEMENT......Page 121
VI. PERSPECTIVE......Page 124
ACKNOWLEDGMENTS......Page 125
REFERENCES......Page 126
CONTENTS......Page 131
II. BIOSYNTHETIC PATHWAYS IN CDG PATHOGENESIS......Page 132
1. CDG-Ia and Ib......Page 136
3. CDG-Id......Page 138
7. CDG-Ih......Page 139
1. CDG-IIa......Page 140
3. CDG-IIc......Page 141
1. Progeroid Variant of Ehlers–Danlos Syndrome......Page 142
2. Hereditary Multiple Exostoses......Page 143
a. Dystrophin Glycoprotein Complex......Page 144
b. Muscular Dystrophies Caused by Presumed Underglycosylation of α-Dystroglycan......Page 146
IV. DIAGNOSIS OF CDG......Page 147
A. ANALYSIS OF ABNORMALLY GLYCOSYLATED REPORTER GLYCOPROTEINS BY SEPARATION TECHNIQUES......Page 148
B. ENZYMATIC ASSAYS......Page 149
C. ANALYSIS OF LLOS AND PROTEIN-LINKED OLIGOSACCHARIDES......Page 150
E. STRUCTURAL METHODS......Page 151
G. DETERMINATION OF GLYCOSPHINGOLIPIDS......Page 154
V. TREATMENT OF CDG......Page 155
REFERENCES......Page 157
NOTE ADDED IN PROOF......Page 172
CONTENTS......Page 173
I. MILK CARBOHYDRATES......Page 174
A. ISOLATION OF THE CRUDE OLIGOSACCHARIDE FRACTION......Page 179
B. SEPARATION AND IDENTIFICATION OF DIFFERENT OLIGOSACCHARIDE COMPONENTS......Page 180
C. ANALYSIS OF INDIVIDUAL OLIGOSACCHARIDES......Page 181
D. FURTHER CHARACTERIZATION......Page 184
III. BACTERIAL ADHESION AND MILK GLYCOCONJUGATES......Page 185
b. Enteropathogenic E. coli (EPEC)......Page 186
d. Enteroinvasive E. coli (EIEC)......Page 188
2. Bacterial Adhesins......Page 189
d. Extracellular Nucleation–Precipitation Pathway......Page 190
3. Glycan Specificity of Bacterial Adhesion......Page 192
B. THE ABILITY OF MILK TO PREVENT BACTERIAL INFECTIONS......Page 195
REFERENCES......Page 198
CONTENTS......Page 208
I. INTRODUCTION......Page 209
A. GLYCOSAMINOGLYCAN CHEMICAL STRUCTURE......Page 211
B. CHALLENGES OF GAG CHARACTERIZATION......Page 213
A. CHEMICAL TECHNIQUES......Page 214
B. ENZYMATIC TECHNIQUES......Page 216
A. CHROMATOGRAPHY......Page 219
B. ELECTROPHORESIS......Page 220
C. NUCLEAR MAGNETIC RESONANCE......Page 221
D. MASS SPECTROMETRY......Page 222
IV. SEQUENCING GLYCOSAMINOGLYCANS......Page 223
V. INFORMATICS-BASED APPROACHES FOR SEQUENCING GLYCOSAMINOGLYCANS......Page 225
A. PEN-MALDI......Page 226
1. Sequencing AT-10......Page 228
B. PEN-NMR......Page 229
C. ADDITIONAL INFORMATICS-BASED APPLICATIONS......Page 231
VI. DIRECT ISOLATION AND SEQUENCING OF GLYCOSAMINOGLYCANS: SNA-MS......Page 233
REFERENCES......Page 235
CONTENTS......Page 242
A. STEPS AND LANDMARKS IN THE HISTORY OF CHEMICAL STUDIES ON CARRAGEENANS: DISCOVERY AND FIRST ATTEMPTS TO STUDY THEIR STRUCTURE......Page 243
C. THIRD PERIOD: LIFE STAGES AND FAMILIES......Page 244
D. APPEARANCE OF AGARAN/CARRAGEENAN HYBRIDS IN CARRAGEENOPHYTES: LATEST STUDIES ON CARRAGEENANS AND HYBRIDS......Page 246
A. CONFORMATIONAL ANALYSIS OF CARBOHYDRATES......Page 247
B. INTRODUCTION TO COMPUTER MODELING OF CARBOHYDRATES: MONOSACCHARIDES......Page 249
C. APPLICATIONS OF MOLECULAR MODELING TO DISACCHARIDES......Page 250
D. X-RAY DIFFRACTION ANALYSIS OF CARRAGEENANS AND MODELS......Page 253
1. Analysis of the Conformation of α-Linked Disaccharides Containing 3,6-Anhydrogalactose (Neocarrabiose)......Page 255
2. Analysis of the Conformation of α-Linked Disaccharides not Containing 3,6-Anhydrogalactose......Page 257
3. Analysis of the Conformation of β-Linked Disaccharides Containing 3,6-Anhydrogalactose (Carrabiose)......Page 260
4. Analysis of the Conformation of β-Linked Disaccharides not Containing 3,6-Anhydrogalactose......Page 263
F. THE THREE-DIMENSIONAL STRUCTURES OF CARRAGEENANS: TERTIARY AND QUATERNARY STRUCTURES......Page 264
REFERENCES......Page 266
CONTENTS......Page 277
I. THE COMPLEXITY OF CARBOHYDRATE STRUCTURE AND SYNTHESIS......Page 278
II. STEPS TOWARD MODELING GLYCOSYLATION......Page 280
III. COMPUTATIONAL MODELING IN METABOLISM......Page 285
A. STOICHIOMETRY: REPRESENTING REACTION EQUATIONS......Page 287
1. Balancing Equations......Page 289
V. MODELING AND CONTROL IN METABOLIC SYSTEMS......Page 290
1. Assumptions of MFA......Page 291
3. Flux Balancing......Page 292
B. METABOLIC CONTROL ANALYSIS (MCA)......Page 294
2. Objections to MCA......Page 295
3. MCA Applied to the Analysis of Sialic Acid Biosynthesis......Page 296
C. BIOCHEMICAL SYSTEMS THEORY (BST)......Page 297
VI. METABOLIC TIME SCALES......Page 298
B. METHODS OF CONTROL COEFFICIENT DETERMINATION......Page 301
B. MODEL VALIDATION......Page 302
C. GLYCOSYLATION LIES AT THE INTERSECTION OF SIGNALING AND METABOLISM......Page 305
REFERENCES......Page 307
I. INTRODUCTION......Page 318
II. BIOSYNTHESIS OF THE GAG–PROTEIN LINKAGE REGION......Page 320
III. BIOSYNTHESIS OF CHONDROITIN BACKBONE......Page 328
IV. SULFATION OF CHONDROITIN BACKBONE......Page 332
V. BIOSYNTHESIS OF HEPARAN SULFATE AND HEPARIN BACKBONES......Page 333
A. N-DEACETYLATION AND N-SULFATION......Page 336
B. URONYL C5 EPIMERIZATION......Page 337
C. O-SULFATION......Page 338
ACKNOWLEDGMENTS......Page 340
REFERENCES......Page 341
I. INTRODUCTION......Page 354
II. BACTERIAL GLYCOSYLTRANSFERASES......Page 355
III. OLIGOSACCHARIDE SYNTHESIS WITH COFACTOR REGENERATION......Page 356
A. SUGAR NUCLEOTIDE PRODUCTION BY BACTERIAL COUPLING......Page 358
B. OLIGOSACCHARIDE PRODUCTION BY BACTERIAL COUPLING......Page 360
V. OLIGOSACCHARIDE PRODUCTION BY FERMENTATION......Page 361
VI. CONCLUSIONS......Page 362
REFERENCES......Page 363
CONTENTS......Page 368
A. AN OVERVIEW OF FRUCTAN......Page 369
C. A PHYSIOLOGICAL CONTEXT FOR TRANSGENIC FRUCTAN SYNTHESIS......Page 370
A. OVERVIEW......Page 371
C. ENDPOINT CONCENTRATIONS AND FLUXES......Page 372
D. EXPLAINING THE LOW RATES OF PRODUCT ACCUMULATION IN THE LEVAN TRANSFORMANTS......Page 376
F. STRUCTURAL IDENTIFICATION OF LEVAN IN TRANSFORMANTS......Page 378
G. HAS SUBCELLULAR TARGETING BEEN ESTABLISHED UNEQUIVOCALLY IN BACTERIAL LEVAN TRANSFORMANTS?......Page 379
H. ABERRANT DEVELOPMENT OF PLANTS TRANSFORMED WITH BACTERIAL LEVANSUCRASE......Page 381
I. MECHANISM OF LEVANSUCRASE-MEDIATED DEVELOPMENTAL EFFECTS......Page 382
J. BENEFICIAL PHENOTYPES RESULTING FROM LEVAN ACCUMULATION......Page 383
B. HIGH-PERFORMANCE ANION-EXCHANGE CHROMATOGRAPHY-PULSED AMPEROMETRIC DETECTION......Page 384
D. EXPLAINING THE LOW RATES PRODUCT ACCUMULATION IN THE PLANT–PLANT TRANSFORMANTS......Page 385
E. TRANSFORMATION OF PLANTS WITH FRUCTOSYLTRANSFERASES FROM HELIANTHUS TUBEROSUS......Page 386
F. TRANSFORMATION OF PLANTS WITH FRUCTOSYLTRANSFERASES FROM CYNARA SCOLYMUS......Page 388
H. TRANSFORMATION OF INULIN-ACCUMULATING PLANTS WITH BARLEY 6-SUCROSE FRUCTOSYLTRANSFERASE......Page 390
J. PHENOTYPIC ABERRATIONS ARE NOT REPORTED FOR PLANT–PLANT TRANSGENICS......Page 391
K. DO RESULTS FROM PLANT–PLANT TRANSGENESIS ADVANCE OUR UNDERSTANDING OF NATURAL FRUCTAN SYNTHESIS?......Page 392
IV. CONCLUSIONS......Page 393
ACKNOWLEDGMENTS......Page 394
REFERENCES......Page 395
I. INTRODUCTION......Page 399
II. BIOCHEMICAL BASES OF CHO GLYCOSYLATION MUTANTS WITH AN ALTERED ARRAY OF CELL SURFACE GLYCANS......Page 401
III. MOLECULAR GENETIC BASES OF LECTIN-RESISTANT CHO GLYCOSYLATION MUTANTS......Page 406
IV. A MULTITUDE OF USES FOR CHO GLYCOSYLATION MUTANTS......Page 407
REFERENCES......Page 408
I. INTRODUCTION......Page 414
A. BIOSYNTHESIS OF NATURAL SIALIC ACIDS......Page 415
B. PATHWAYS FOR UNNATURAL SIALIC ACIDS......Page 417
A. BIOLOGICAL EFFECTS OF UNNATURAL SIALIC ACIDS......Page 422
B. BIOMEDICAL APPLICATIONS......Page 424
ACKNOWLEDGMENTS......Page 427
REFERENCES......Page 428
I. INTRODUCTION......Page 433
II. GLYCOSYLATION IN NATIVE INSECT CELLS......Page 435
A. MAMMALIAN N-GLYCAN PROCESSING......Page 436
B. INSECT CELLS N-GLYCAN PROCESSING......Page 438
C. AVAILABILITY OF SUGAR NUCLEOTIDES INVOLVED IN N-LINKED GLYCOSYLATION......Page 440
D. CMP-NEU5AC SYNTHESIS PATHWAY IN MAMMALS AND INSECTS......Page 441
III. METABOLIC ENGINEERING OF GLYCOSYLATION PATHWAYS IN INSECT CELLS......Page 442
A. ENGINEERING GLYCOSYLTRANSFERASE AND INHIBITING GLUCOSAMINIDASE ACTIVITIES IN INSECT CELLS......Page 443
B. GENERATION OF CMP-NEU5AC SIALYLATION SUBSTRATES IN INSECT CELLS......Page 445
C. NONMETABOLIC-ENGINEERING APPROACHES TO SYNTHESIZE COMPLEX-TYPE GLYCANS IN INSECT CELLS......Page 446
IV. CONCLUDING REMARKS......Page 447
REFERENCES......Page 448
CONTENTS......Page 457
I. INTRODUCTION......Page 458
A. BIOSYNTHESIS OF THE SUGAR-NUCLEOTIDE DONOR SUBSTRATES OF GLYCOSYLATION REACTIONS: CYTOPLASMIC EVENTS......Page 459
1. UDP-GlcNAc and UDP-GalNAc......Page 461
2. CMP-NANA......Page 463
3. GDP-Man......Page 464
5. UDP-Gal......Page 465
B. TRANSPORT OF SUGAR NUCLEOTIDES TO THE ER/GOLGI LUMEN AND “FLIPPING” OF THE DOL-P-MAN AND DOL-P-GLC SUBSTRATES TO THE LUMINAL MEMBRANE SIDE......Page 466
C. ASSEMBLY OF THE DOLICHOL-OLIGOSACCHARIDE PRECURSOR: ER MEMBRANE-BOUND EVENTS......Page 467
D. DEGLUCOSYLATION AND REGLUCOSYLATION: ROLE IN GLYCOPROTEIN FOLDING......Page 471
E. S. CEREVISIAE GOLGI N-GLYCAN PROCESSING PATHWAY......Page 473
F. HUMAN GOLGI N-GLYCAN PROCESSING I: PATHWAY TOWARD BIANTENNARY SIALYLATED GLYCANS......Page 474
G. HUMAN GOLGI N-GLYCAN PROCESSING II: FURTHER COMPLEXITY BY HIGHER BRANCHING, BRANCH ELONGATION AND BRANCH SUBSTITUTION......Page 477
1. Yeasts other than S. cerevisiae......Page 478
A. ENGINEERING GOALS: N-GLYCAN HOMOGENIZATION AND GENERATION OF HUMAN-COMPLEX-TYPE STRUCTURES......Page 479
B. ENGINEERING IN THE MODEL: S. CEREVISIAE......Page 481
C. N-GLYCAN ENGINEERING IN P. PASTORIS......Page 482
D. N-GLYCAN ENGINEERING IN FILAMENTOUS FUNGI......Page 487
REFERENCES......Page 492
I. INTRODUCTION......Page 505
II. INDUSTRIAL APPLICATIONS OF MICROBIAL POLYSACCHARIDES......Page 506
III. BIOMEDICAL APPLICATIONS OF MICROBIAL POLYSACCHARIDES......Page 507
V. GENETIC ORGANIZATION AND REGULATION OF E. COLI GROUP 2 CAPSULE GENE CLUSTERS......Page 508
VII. CHONDROITIN SYNTHASES......Page 513
VIII. HEPAROSAN SYNTHASES......Page 514
IX. APPROACHES TO SYNTHESIS OF BIOTECHNOLOGICAL HEPARIN......Page 515
REFERENCES......Page 516
I. INTRODUCTION......Page 521
A. INCORPORATION OF SYNTHETIC PRECURSORS INTO THE BACTERIAL CELL WALL......Page 524
B. ADHESION OF SURFACE-ENGINEERED BACTERIA TO THE CON A-IMMOBILIZED FILM BY DISPLAYING CARBOHYDRATES......Page 526
C. MODIFICATION OF CELL-WALL PRECURSORS......Page 527
D. ENHANCEMENT OF INCORPORATION EFFICIENCY BY ANTIBIOTICS......Page 529
II. CONCLUSIONS......Page 530
REFERENCES......Page 531
I. INTRODUCTION......Page 532
A. CATION BINDING TO BACTERIAL BIOPOLYMERS......Page 534
B. CATION BINDING TO EMULSAN AND OTHER AMPHIPATHIC BIOPOLYMERS......Page 541
C. EMULSIFICATION ENHANCEMENT, NOVEL ESTERASE FORMULATIONS......Page 543
D. POLYSACCHARIDE ENGINEERING AND CATION BINDING......Page 545
III. POTENTIAL APPLICATIONS......Page 548
B. DRIED PACKED BIOMASS......Page 550
E. ACTIVATED SLUDGE......Page 551
REFERENCES......Page 552
I. INTRODUCTION......Page 560
A. FOOD-PROCESSING WASTEWATER......Page 561
B. METAL-CONTAMINATED WASTEWATER......Page 564
C. DYE WASTEWATER......Page 572
1. Phenol-Contaminated Wastewater......Page 576
2. PCB-Contaminated Wastewater......Page 577
III. CONCLUSIONS......Page 579
REFERENCES......Page 580
I. INTRODUCTION......Page 588
A. IgG......Page 589
B. IgA......Page 590
A. GLYCOSYLATION OF IgG AND INTERACTIONS WITH FcγRs......Page 591
B. COMPLEMENT......Page 593
C. HALF-LIFE......Page 595
E. SECRETION......Page 597
IV. VARIABLE REGION GLYCOSYLATION......Page 598
V. EXPRESSION SYSTEMS FOR THE PRODUCTION OF RECOMBINANT ANTIBODIES......Page 599
B. INSECT CELLS......Page 600
C. PLANTS......Page 601
E. MAMMALIAN CELL LINES......Page 602
ACKNOWLEDGMENTS......Page 603
REFERENCES......Page 604
CONTENTS......Page 612
I. INTRODUCTION......Page 613
B. 2-DEOXYGLYCOSIDES......Page 615
III. SYNTHESIS OF OLIGOSACCHARIDES BY THERMOPHILIC GLYCOSYNTHASES......Page 618
A. HYPERTHERMOPHILIC β-GLYCOSYNTHASE FROM S. SOLFATARICUS......Page 619
B. IMPROVING THE PERFORMANCE OF HYPERTHERMOPHILIC GLYCOSYNTHASE......Page 621
IV. α-XYLOSIDASE FROM S. SOLFATARICUS......Page 624
V. α-L-FUCOSIDASE FROM S. SOLFATARICUS......Page 627
A. IDENTIFICATION AND CHARACTERIZATION OF THE FIRST ARCHAEAL α-L-FUCOSIDASE......Page 628
B. TRANSFUCOSYLATION REACTIONS......Page 629
C. IDENTIFICATION OF THE NUCLEOPHILE......Page 630
ACKNOWLEDGMENTS......Page 632
REFERENCES......Page 633
CONTENTS......Page 638
I. INTRODUCTION......Page 639
B. XYLAN......Page 640
E. PECTIN......Page 641
III. MOLECULAR ARCHITECTURE OF THE CELL WALL......Page 642
1. Enzymes Involved in Cellulose Degradation......Page 644
1. Enzymes Involved in Xylan Degradation......Page 645
2. Enzymatic Modification of Xylan......Page 646
1. Enzymes Involved in Galacto(Gluco)Mannan Degradation......Page 647
2. Enzymatic Modification of Galacto(Gluco)Mannan......Page 648
1. Enzymes Involved in Pectin Degradation......Page 649
2. Enzymatic Modification of Pectin......Page 651
A. PRODUCTION OF PLANT CELL WALL POLYSACCHARIDE-DEGRADING ENZYMES ON CRUDE AND DEFINED CARBON SOURCES......Page 652
3. Gene Expression Induced by D-Mannose and D-Galactose......Page 653
1. Carbon Catabolite Repression......Page 654
VI. CONCLUDING REMARKS......Page 655
REFERENCES......Page 656
I. INTRODUCTION......Page 670
II. METHODS FOR ASSAY OF β-GLUCOSIDASE......Page 671
III. SUBSTRATE SPECIFICITY......Page 673
IV. EFFECT OF TEMPERATURE AND pH ON ACTIVITY AND STABILITY......Page 679
V. EFFECT OF INHIBITORS......Page 684
VI. ENZYME PURIFICATION......Page 689
VIII. CARBOHYDRATE CONTENT......Page 690
IX. ISOENZYME FORMS......Page 691
X. SEQUENCE AND STRUCTURE......Page 692
XI. BIOTECHNOLOGICAL APPLICATIONS......Page 697
XII. CONCLUSIONS......Page 699
REFERENCES......Page 700
I. INTRODUCTION......Page 711
II. SIALIC ACIDS AND SIALYLMIMETICS AS PROBES FOR SIALIDASES......Page 713
A. INFLUENZA VIRUS SIALIDASE......Page 714
1. C-4 Modification......Page 717
2. C-5 Modifications......Page 719
3. Glycerol Side Chain Modification......Page 720
4. Cyclohexene Scaffold......Page 723
5. Cyclopentane Template......Page 728
6. Aromatic Template......Page 730
B. VIBRIO CHOLERAE SIALIDASE......Page 731
III. SIALYLMIMETICS AS PROBES FOR SELECTINS......Page 737
A. PENTA- AND TETRASACCHARIDE-BASED SLEX MIMETICS......Page 741
B. TRISACCHARIDE-BASED SLEX MIMETICS......Page 744
C. DISACCHARIDE-BASED SLEX MIMETICS......Page 746
D. MONOSACCHARIDE-BASED SLEX MIMETICS......Page 747
E. NONCARBOHYDRATE-BASED SLEX MIMETICS......Page 751
IV. SIALYLMIMETICS AS PROBES FOR OTHER SIALIC ACID-RECOGNIZING PROTEINS......Page 752
REFERENCES......Page 756
CONTENTS......Page 773
A. NATURALLY OCCURRING SAAHS......Page 774
II. CLASSIFICATION AND PROPERTIES OF SAAH BUILDING BLOCKS......Page 775
A. SUGAR AMINO ACID BUILDING BLOCKS......Page 776
B. GLYCOSYL AMINO ACIDS......Page 777
C. DOUBLE-SUBSTITUTED GLYCOSYL AMINO ACIDS......Page 779
E. AZASUGAR ACIDS......Page 780
III. HOMOOLIGOMERIZATION OF SUGAR AMINO ACIDS — ACCESS TO OLIGOSACCHARIDE MIMETICS......Page 781
IV. INCORPORATION OF SAAHS INTO BIOACTIVE PEPTIDES......Page 786
B. LIBRARY SYNTHESIS USING GAAS DERIVED FROM O- AND N-LINKED GLYCOPEPTIDES......Page 789
C. LIBRARY SYNTHESIS USING GAAS WHICH ARE NOT DERIVED FROM O- AND N-LINKED GLYCOPEPTIDES......Page 792
D. COMBINATORIAL APPROACHES TOWARD GLYCOPEPTIDES DERIVED FROM GAAS (A2 TYPE)......Page 793
F. ACCESS TO AZA SUGAR ACID LIBRARIES......Page 795
ACKNOWLEDGMENTS......Page 797
REFERENCES......Page 798
I. INTRODUCTION......Page 804
II. DESCRIPTION AND NATURAL OCCURRENCE......Page 805
III. EPIDEMIOLOGY AND ANIMAL STUDIES......Page 806
IV. EXPERIMENTAL DESIGN......Page 807
V. EFFECT ON MICROFLORA......Page 809
VI. FERMENTATION, SCFA, AND pH......Page 810
VII. CELL PROLIFERATION......Page 812
VIII. PRENEOPLASTIC CHANGES (ACF)......Page 813
IX. OTHER CLINICAL EFFECTS......Page 814
X. CONCLUSIONS......Page 815
REFERENCES......Page 816
I. INTRODUCTION......Page 822
II. ALGINIC ACID AND ALGINATE......Page 824
III. ALGINATE-BASED DRUG DELIVERY SYSTEMS......Page 826
B. THE COMPOSITION OF ALGINATE......Page 827
E. ADDITION OF SUBSTANCES THAT MODULATE THE PROPERTIES OF ALGINATE......Page 828
A. FLOATING OR GASTRORETENTIVE DRUG DELIVERY SYSTEM......Page 830
C. ALGINATE NANOPARTICLES......Page 831
VI. ENCAPSULATION OF ANTITUBERCULAR DRUGS IN ALGINATE MICROSPHERES......Page 832
VII. ENCAPSULATION OF PROTEINS, DNA, AND CELLS IN ALGINATE......Page 834
B. ENCAPSULATION OF ANDROGEN-PRODUCING CELLS......Page 835
VIII. SUMMARY......Page 836
REFERENCES......Page 837
I. INTRODUCTION......Page 839
III. TRANSMEMBRANE CHARACTERISTICS......Page 841
A. MOLECULAR WEIGHT–TRANSFECTION RELATIONSHIP (MWTR)......Page 843
B. APPLICATIONS OF CHITOSAN IN MESENCHYMAL STEM-CELL TRANSFECTION......Page 845
C. ADMINISTRATION ROUTE OF CHITOPLEXES......Page 847
V. CHITOSAN DERIVATIVE VECTORS IN GENE DELIVERY......Page 849
B. ALKYLATED CHITOSAN VECTORS......Page 850
C. GALACTOSYLATED CHITOSAN VECTORS......Page 851
REFERENCES......Page 854
CONTENTS......Page 859
I. INTRODUCTION......Page 860
B. POROUS SOLIDS......Page 862
D. HYDROGELS......Page 863
E. CELL ENCAPSULATION......Page 864
B. NATURAL POLYMERS......Page 865
B. AGAROSE......Page 866
C. ALGINATES......Page 867
1. Wound Dressing......Page 868
3. Cell Encapsulation......Page 869
4. Scaffold/Cell Constructs......Page 870
D. CHITIN/CHITOSAN......Page 873
1. Wound Healing......Page 875
2. Drug Delivery......Page 878
3. Gene Delivery......Page 880
4. Scaffold/Cell Constructs......Page 882
E. DEXTRAN......Page 886
1. Introduction......Page 892
2. Hyaluronan......Page 893
4. Heparin......Page 896
V. NEW TRENDS AND DEVELOPMENTS......Page 897
REFERENCES......Page 898