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1 About this book, and how to use it 1
The subject 1
The aim 1
The approach 2
The topics 2
The figures 2
Further reading 3
What to study 3
What to learn 3
Nomenclature 3
Conventions regarding acids, bases, and ions 4
Some common abbreviations 4
Further reading 5
2 Secondary metabolism: the building blocks and construction mechanisms 7
Primary and secondary metabolism 7
The building blocks 8
The construction mechanisms 11
Alkylation reactions: nucleophilic substitution 12
Alkylation reactions: electrophilic addition 12
Wagner-Meerwein rearrangements 15
Aldol and Claisen reactions 15
Imine formation and the Mannich reaction 18
Amino acids and transamination 20
Decarboxylation reactions 22
Oxidation and reduction reactions 24
Dehydrogenases 24
Oxidases 26
Monooxygenases 26
Dioxygenases 26
Amine oxidases 27
Baeyer-Villiger monooxygenases 27
Phenolic oxidative coupling 28
Halogenation reactions 28
Glycosylation reactions 31
Elucidating biosynthetic pathways 34
Further reading 38
3 The acetate pathway: fatty acids and polyketides 39
Fatty acid synthase: saturated fatty acids 39
Unsaturated fatty acids 44
Uncommon fatty acids 53
Prostaglandins 58
Thromboxanes 64
Leukotrienes 64
Polyketide synthases: generalities 66
Polyketide synthases: macrolides 68
Polyketide synthases: linear polyketides and polyethers 90
Diels-Alder cyclizations 96
Polyketide synthases: aromatics 96
Cyclizations 99
Post-polyketide synthase modifications 103
Starter groups 116
Further reading 131
4 The shikimate pathway: aromatic amino acids and phenylpropanoids 137
Aromatic amino acids and simple benzoic acids 137
Phenylpropanoids 148
Cinnamic acids and esters 148
Lignans and lignin 152
Phenylpropenes 156
Benzoic acids from C6C3 compounds 157
Coumarins 161
Aromatic polyketides 166
Styrylpyrones, diarylheptanoids 166
Flavonoids and stilbenes 167
Flavonolignans 173
Isoflavonoids 174
Terpenoid quinones 178
Further reading 184
5 The mevalonate and methylerythritol phosphate pathways: terpenoids and steroids 187
Mevalonic acid and methylerythritol phosphate 188
Hemiterpenes (C5) 192
Monoterpenes (C10) 193
Irregular monoterpenes 204
Iridoids (C10) 206
Sesquiterpenes (C15) 210
Diterpenes (C20) 223
Sesterterpenes (C25) 234
Triterpenes (C30) 234
Triterpenoid saponins 242
Steroids 247
Stereochemistry and nomenclature 247
Cholesterol 248
Phytosterols 251
Vitamin D 256
Steroidal saponins 259
Cardioactive glycosides 265
Bile acids 275
Adrenocortical hormones/corticosteroids 277
Semi-synthesis of corticosteroids 277
Progestogens 287
Oestrogens 290
Androgens 296
Tetraterpenes (C40) 298
Higher terpenoids 306
Further reading 306
6 Alkaloids 311
Alkaloids derived from ornithine 311
Polyamines 311
Pyrrolidine and tropane alkaloids 312
Pyrrolizidine alkaloids 324
Alkaloids derived from lysine 326
Piperidine alkaloids 326
Quinolizidine alkaloids 328
Indolizidine alkaloids 330
Alkaloids derived from nicotinic acid 331
Pyridine alkaloids 331
Alkaloids derived from tyrosine 336
Phenylethylamines and simple tetrahydroisoquinoline alkaloids 336
Modified benzyltetrahydroisoquinoline alkaloids 346
Phenethylisoquinoline alkaloids 359
Terpenoid tetrahydroisoquinoline alkaloids 363
Amaryllidaceae alkaloids 365
Alkaloids derived from tryptophan 366
Simple indole alkaloids 366
Simple ß-carboline alkaloids 369
Terpenoid indole alkaloids 369
Quinoline alkaloids 380
Pyrroloindole alkaloids 385
Ergot alkaloids 387
Alkaloids derived from anthranilic acid 395
Quinazoline alkaloids 395
Quinoline and acridine alkaloids 396
Alkaloids derived from histidine 398
Imidazole alkaloids 398
Alkaloids derived by amination reactions 400
Acetate-derived alkaloids 401
Phenylalanine-derived alkaloids 401
Terpenoid alkaloids 406
Steroidal alkaloids 406
Purine alkaloids 413
Caffeine 413
Saxitoxin and tetrodotoxin 416
Further reading 417
7 Peptides, proteins, and other amino acid derivatives 421
Peptides and proteins 421
Ribosomal peptide biosynthesis 422
Peptide hormones 426
Thyroid hormones 426
Hypothalamic hormones 427
Anterior pituitary hormones 429
Posterior pituitary hormones 430
Pancreatic hormones 432
Interferons 433
Opioid peptides 434
Ribosomal peptide toxins 434
Enzymes 438
Non-ribosomal peptide biosynthesis 438
Modified peptides: penicillins, cephalosporins, and other ß-lactams 458
Penicillins 458
Cephalosporins 465
Other ß-lactams 469
Cyanogenic glycosides 476
Glucosinolates 477
Cysteine sulfoxides 480
Further reading 481
8 Carbohydrates 485
Monosaccharides 485
Oligosaccharides 490
Polysaccharides 493
Aminosugars and aminoglycosides 498
Further reading 507
Index 509
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