search for books and compare prices
Tables of Contents for Essentials of Carbohydrate Chemistry
Chapter/Section Title
Page #
Page Count
Series Preface
v
2
Preface
vii
2
Acknowledgments
ix
Chapter 1 Beginnings
1
18
1.1 Carbohydrates and Their Involvement in Life Processes
1
1
1.2 The Nature of Carbohydrates
2
1
1.3 Occurrence of Carbohydrates
3
2
1.4 Asymmetry and the Structures of Carbohydrates
5
5
1.5 Remembering the Structures of Carbohydrates
10
3
1.6 Derived Carbohydrate Structures
13
5
a. Sugar Alcohols
13
1
b. Sugar Acids
13
2
c. Deoxy Sugars
15
1
d. Amino Sugars
15
3
e. Sugar Phosphates
18
1
f. Condensed Sugar Products
18
1
1.7 Literature Cited
18
1
Chapter 2 Developments
19
29
2.1 Carbohydrates in the History and Development of Human Culture
19
2
2.2 Development of Carbohydrate Chemistry
21
6
a. Chemical Properties of Carbohydrates, 1860-1880
22
1
b. Fischer's Demonstration of the Structures of Glucose, Mannose, Arabinose, and Fructose
23
4
2.3 Cyclic Structures for the Carbohydrates
27
6
2.4 Naming the Anomeric Forms of Carbohydrates
33
1
2.5 Determination of the Size of Carbohydrate Rings
33
3
2.6 Conformational Structures of Cyclic Sugars
36
3
2.7 The Literature of Carbohydrate Chemistry
39
3
2.8 Chronological Summary of the Uses of Carbohydrates by Humans and the Development of Carbohydrate Chemistry
42
2
2.9 Specific Terms and Concepts Used in Carbohydrate Chemistry
44
3
2.10 Literature Cited
47
1
2.11 References for Further Study
47
1
Chapter 3 Transformations
48
28
3.1 Mutarotation
48
2
3.2 Reactions of Carbohydrates with Strong Alkali
50
3
3.3 Alkaline Dehydration, Fragmentation, and Oxidation Reactions of Carbohydrates
53
1
3.4 Reactions of Carbohydrates with Strong Acid, and the Qualitative and Quantitative Determination of Carbohydrates
53
7
3.5 Reducing Reactions of Carbohydrates
60
4
3.6 Reactions of Hemiacetals or Hemiketals with Alcohols
64
2
3.7 Formation of Glycosidic Linkages to Give Di-, Tri-, and Oligosaccharides
66
7
3.8 Literature Cited
73
1
3.9 References for Further Study
74
2
Chapter 4 Modifications
76
66
4.1 Formation of Carboxylic Acid Esters
77
4
4.2 Formation of Sulfonic Acid Esters
81
2
4.3 Formation of Ethers
83
2
a. Methyl Ethers
83
1
b. Trityl Ethers
83
1
c. Benzyl Ethers
84
1
d. Trialkylsilyl Ethers
85
1
4.4 Formation of Acetals and Ketals
85
7
4.5 Modifications at C-1
92
16
a. Reduction of Aldehyde and Ketone Carbonyls
92
1
b. Reduction of Thioacetals and the Protection of C-1
93
1
c. Oxidation of C-1
93
1
d. Chain Elongation
94
4
e. Chain-Length Reduction
98
1
f. Substitution at C-1, the Reducing Carbon
99
4
g. Formation of Glycosides
103
2
h. Formation of Glycosidic Linkages between Monosaccharide Residues
105
3
4.6 Modifications at C-2
108
5
4.7 Modifications at C-3
113
8
4.8 Modifications at C-4
121
4
4.9 Modifications at C-5 and Substitution for the Ring Oxygen
125
3
4.10 Modifications of C-6 in Hexopyranoses
128
7
4.11 Summary of the Strategies Presented for the Chemical Modification of Carbohydrates
135
2
4.12 Literature Cited
137
3
4.13 References for Further Study
140
2
Chapter 5 Sweetness
142
15
5.1 The Sweet Taste of Sugars and the Development of the Sweet-Taste Hypothesis
142
4
5.2 Naturally Occurring Sweet Glycosides
146
2
5.3 Synthesis of Supersweet Sucroses
148
7
5.4 Literature Cited
155
1
5.5 References for Further Study
155
2
Chapter 6 Polysaccharides I: Structure and Function
157
71
6.1 Introduction: Structure and Classification of Polysaccharides
157
3
6.2 Plant Polysaccharides
160
27
a. Starch
160
8
b. Cellulose
168
3
c. Hemicelluloses
171
4
d. Pectins
175
2
e. Exudate Gums
177
2
f. Fructans
179
1
g. Seaweed Polysaccharides
180
7
h. Dietary Fibers
187
1
6.3 Animal Polysaccharides
187
6
a. Glycogen
187
2
b. Glycosaminoglycans
189
3
c. Chitin
192
1
6.4 Microbial Polysaccharides
193
17
a. Murein
193
1
b. Dextrans and Related Polysaccharides: Mutan and Alternan
194
4
c. Pullulan
198
1
d. Bacterial Fructans
198
2
e. Xanthan
200
2
f. Bacterial Gels
202
2
g. Pneumococcal Capsule Polysaccharides
204
2
h. Salmonella O-Antigen Polysaccharides
206
2
i. Capsular Polysaccharides of Other Gram-Negative Bacteria
208
2
6.5 Teichoic Acids
210
5
6.6 Simplified Representation of Oligosaccharide and Polysaccharide Structures
215
3
6.7 Literature Cited
218
8
6.8 References for Further Study
226
2
Chapter 7 Polysaccharides II: Chemical Modifications and Their Applications
228
17
7.1 Introduction
228
1
7.2 Formation of Polysaccharide Esters
229
2
7.3 Formation of Polysaccharide Ethers
231
3
7.4 Formation of Cross-linked Polysaccharide Ethers
234
1
7.5 Polysaccharide Phosphates
235
3
7.6 Polysaccharide Sulfates
238
1
7.7 Polysaccharide Dye Derivatives
238
1
7.8 Activation of Polysaccharides for Covalently Attaching Ligands and Proteins
239
1
7.9 Oxidation of Primary Alcohols of Polysaccharides to Carboxyl Groups
240
1
7.10 Periodate Oxidation of Polysaccharides
240
1
7.11 Miscellaneous Modifications of Alcohol Groups of Polysaccharides
241
1
7.12 Modification of Starch Granules by Acid Hydrolysis
241
2
7.13 Literature Cited
243
2
Chapter 8 Cyclodextrins
245
17
8.1 Cyclomaltodextrins
245
6
8.2 Cyclic XXX-1 -> 2 Glucans (Cyclosophorans)
251
1
8.3 Cyclic XXX-1 -> 6 and XXX+-1 -> 3 D-Glucans
252
2
8.4 Cycloisomaltodextrins
254
1
8.5 Cycloalternanotetraose (Alternating XXX-1 -> 6/XXX-1 -> 3 Cyclotetraose)
255
1
8.6 Cycloinulodextrin
256
1
8.7 Chemical Synthesis of Cyclodextrins
256
2
8.8 Macrocyclic Maltodextrins
258
1
8.9 Literature Cited
258
3
8.10 References for Further Study
261
1
Chapter 9 Glycoconjugates
262
28
9.1 Introduction
262
2
9.2 Structures of N-Linked Glycosides in Glycoproteins
264
10
9.3 Structures of O-Linked Glycosides in Glycoproteins
274
5
9.4 Structures of Glycolipids
279
8
a. Glycoglycerolipids
279
1
b. Glycosphingolipids
280
4
c. Glycosyl Pyrophospho Polyprenols
284
1
d. Lipopolysaccharide of Gram-Negative Bacteria
284
3
9.5 Literature Cited
287
2
9.6 References for Further Study
289
1
Chapter 10 Biosynthesis
290
38
10.1 Photosynthesis and the Formation of Carbohydrates
290
8
10.2 Biosynthesis of Sugar Nucleotides
298
1
10.3 Biosynthesis of Different Monosaccharides by Epimerization, Oxidation, and Decarboxylation
299
2
10.4 Biosynthesis of D- and L-6-Deoxyhexoses
301
1
10.5 Biosynthesis of Eight- and Nine-Carbon Sugars: N-Acetyl-D-Neuraminic Acid, N-Acetyl-D-Muramic Acid, and 2-Keto-3-Deoxy-D-Mannooctulosonic Acid (KDO)
301
3
10.6 Biosynthesis of the Naturally Occurring Disaccharides: XXX, XXX-Trehalose, Sucrose, and Lactose
304
1
10.7 Biosynthesis of Sucrose and Starch in Plants
304
1
10.8 Biosynthesis of the Bacterial Cell Wall: Peptidomurein
305
6
10.9 Biosynthesis of the Salmonella O-Antigen Outer Capsular Polysaccharide
311
1
10.10 Biosynthesis of Escherichia coli and Neisseria meningitidis Colominic Acid
311
2
10.11 Biosynthesis of Teichoic Acids
313
1
10.12 Biosynthesis of Dextrans and Related Polysaccharides
313
5
10.13 Biosynthesis of Starch, Glycogen, and Cellulose
318
4
10.14 Biosynthesis of Glycoproteins
322
2
10.15 Literature Cited
324
3
10.16 References for Further Study
327
1
Chapter 11 Biodegradation
328
17
11.1 Digestion of Starch
328
3
11.2 Hydrolysis of Starch by Microorganisms
331
2
11.3 Biodegradation of Starch and Dextran to Cyclodextrins
333
2
11.4 Biodegradation of Liver and Muscle Glycogen
335
1
11.5 Biodegradation of Cellulose and Related Polysaccharides
336
1
11.6 Chemical Energy from Carbohydrates
337
6
11.7 Literature Cited
343
2
Chapter 12 Determinations
345
20
12.1 Determination of the Presence of Carbohydrate
345
1
12.2 Purification of Carbohydrates
345
1
12.3 Monosaccharide Composition of Carbohydrates
346
1
12.4 Determination of the Positions of Glycosidic Linkage
347
1
12.5 Determination of the Position of Substitution of Monosaccharide Residue(s) by Periodate Oxidation
348
2
12.6 Configuration of Glycosidic Linkages
350
2
12.7 Sequence of Monosaccharides and Their Linkages
352
1
12.8 Use of Enzymes in Determining Structure
352
3
12.9 Determination of Carbohydrate Structure by Using NMR
355
4
12.10 Separation and Determination of Carbohydrate Structure by Using Lectins
359
2
12.11 Removal of Glycosides from Glycoproteins for Structure Determination
361
1
12.12 Literature Cited
362
2
12.13 References for Further Study
364
1
Appendix A Primer on Carbohydrate Nomenclature
365
12
Appendix B Primer on Enzyme Names and Their Catalyzed Reactions
377
8
Index
385