1st Edition
Natural Product Chemistry A mechanistic, biosynthetic and ecological approach
This book will be of interest to senior undergraduate and postgraduate students of organic chemistry, biochemistry, biology and pharmacology, medical chemistry and research laboratories.
Prefaces
Chapter 1 Introduction and general considerations
- The literature
- Background
- Synthesis and biosynthesis
- Primary and secondary metabolism
- Biochemical reactions and organic reaction mechanisms
- Principal pathways
- The one carbon fragment
- Elucidation of metabolic sequences
- Prebiotic chemistry
Bibliography
Chapter 2 Chemical Ecology
2.1 Introduction. General. Definitions.
2.2 Adaptation to the environment
2.3 Chemistry of pollination
2.4 Plant-animal relationships
Insect feeding stimulants and repellents
The chemistry of plant defense
Hormone interactions
2.5 Animal-animal relationship
2.5.1 Chemical defense and warfare
2.5.2 Pheromones
Sex Pheromones
Alarm and aggregation pheromones
Trial pheromones
Oviposition pheromones
Territorial pheromones
2.6 Plant-plant relationships
2.7 Plant-microorganism relationships. Phytoalexins.
Bibliography
Chapter 3 Carbohydrates and primary metabolites
3.1 Classification. Structure of glucose
3.2 Conformation and stereoisomerism
3.3 Photosynthesis
3.4 Breakdown of glucose. Glycolysis. The citric acid cycle
3.5 Monosaccharides
3.6 Disaccharides and glycosides
3.7 Polysaccharides
3.8 Problems
Bibliography
Chapter 4 The shikimic acid pathway
4.1 Biosynthesis of shikimic acid
4.2 Aromatic amino acids
4.3 Biological hydroxylation. Redox reactions
4.4 Cinnamic and benzoic acids
4.5 Coumarins
4.6 Quinones
4.7 Lignin constituents
4.8 Total synthesis
4.9 Problems
Bibliography
Chapter 5 The polyketide pathway
5.1 Introduction
5.2 Fatty acids, fats
5.3 Branched fatty acids
5.4 Olefinic acids. Prostaglandins
5.5 Acetylenic compounds
5.6 Macrolides
5.7 Polyethers
5.8 B-Oxidation
5.9 Cyclization of polyketides to aromatics
5.10 Confirmation of the acetate hypothesis. The use of NMR in biosynthetic studies
5.11 Derivation of structure
5.12 Anthraquinones, anthracyclinones and tetracyclines
5.13 Flavonoids
5.14 Tropolones
5.15 Oxidative coupling of Phenols
5.16 Halogen compounds
5.17 Modification of the carbon skeleton
5.18 Problems
Bibliography
Chapter 6 The mevalonic acid pathway. The terpenes
6.1 Introduction
6.2 Biosynthesis of mevalonic acid and the active isoprene units. The chiral methyl
6.3 Monoterpenes
6.4 Sesquiterpenes
6.5 Diterpenes
6.6 Sesterterpenes
6.7 Squalene. Triterpenes
6.8 Secondary modifications of triterpenes
6.9 Steroids
6.10 Carotenes. Polymers
6.11 Optical rotary dispersion and circular dichroism. The octant rule
6.12 Problems
Bibliography
Chapter 7 Amino acids, peptides and proteins
7.1 Introduction
7.2 Amino Acids. Classification, structure and properties
7.3 Reactions of amino acids promoted by pyridoxal phosphate
7.4 The guanidine function
7.5 Secondary products from serine and cysteine
7.6 Secondary products from valine, leucine and isoleucine
7.7 Cyanogenic glycosides and glucosinolates
7.8 Peptides, B-lactam antibiotics and proteins
7.9 Problems
Bibliography
Chapter 8 The alkaloids
8.1 Introduction
8.2 Alkaloids derived from ornithine and lysine. The pyrrolidine and piperidine alkaloids
8.3 Alkaloids derived from tyrosine
8.4 Alkaloids derived from tryptophan. The indole alkaloids
8.5 Alkaloids derived from anthranilic acid
8.6 Alkaloids derived by amination of terpenes
8.7 Problems
Bibliography
Chapter 9 N-Heteroaromatics
9.1 Introduction
9.2 Pyrimidines, purines and pteridines
9.3 Pyrroles and porphyrins
9.4 Biosynthesis of the corrin skeleton
9.5 Reactions of vitamin B₁₂
9.6 Retrospect and prospect
Bibliography
Answers to problems
Subject Index
Biography
Kurt B.G. Torssell
