9781405145626

Natural Product Chemistry at a Glance

by
  • ISBN13:

    9781405145626

  • ISBN10:

    1405145625

  • Edition: 1st
  • Format: Paperback
  • Copyright: 2006-08-11
  • Publisher: Wiley-Blackwell
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Summary

Natural products have been a fertile area of chemical investigation for many years, driving the development of both analytical chemistry and of new synthetic reactions and methodologies. Many of the most important synthetic reactions in chemistry have been developed in the quest to characterise and synthesise these materials. Natural Product Chemistry at a Glance provides a concise overview of the main principles and reactions of natural product chemistry, for students studying chemistry and related courses at undergraduate level. Based on the highly successful and student friendly "at a glance" approach, the material developed in this book has been chosen to reinforce the principles of elementary organic reactions and to highlight the similarity between many organic reactions and biological processes. It will also serve as an initial platform for more advanced excursions into the origin of natural products. Students using Natural Product Chemistry at a Glance will find they have a resource with which they can quickly, economically and confidently acquire, regularly review and revise the basic facts that underpin the biosynthesis and chemistry of natural products.

Author Biography

Stephen Stanforth is a Reader in the School of Applied Sciences, Northumbria University, Newcastle upon Tyne, UK.

Table of Contents

Introduction
1(6)
Primary and Secondary Metabolites
2(4)
Properties and Purpose of Secondary Metabolites
6(1)
Acetyl Coenzyme A: A Key Biological Intermediate
7(8)
What is Acetyl Coenzyme A?
8(1)
Comparison of Organic and Acetyl Coenzyme A Reactions
9(1)
Malonyl Coenzyme A -- A Partnership with Acetyl Coenzyme A
10(2)
How is Acetyl Coenzyme A Used in Biosynthesis?
12(3)
Biosynthesis of Fatty Acids
15(20)
What are Fatty Acids?
16(1)
Occurrence and Function of Fatty Acids
17(1)
Biosynthesis of Saturated Straight-Chain Fatty Acids
18(4)
Biosynthesis of Saturated Branched Fatty Acids
22(2)
Mono-unsaturated Fatty Acids
24(2)
Poly-unsaturated Fatty Acid
26(2)
Oxygenated Fatty Acids
28(4)
β-Oxidation
32(3)
Biosynthesis of Polyketides
35(32)
What are Polyketides?
36(1)
The Chemistry of 1,3-Dicarbonyls: Keto--Enol Tautomerism
37(1)
The Chemistry of 1,3-Dicarbonyls: Condensation Reactions
38(2)
Polyketide Cyclizations: Formation of Unsaturated Products
40(2)
Secondary Structural Modifications During Polyketide Cyclizations
42(18)
Alkylation
42(6)
Reduction
48(4)
Oxidation
52(5)
Decarboxylation
57(1)
Modifications to the Carbon Skeleton
58(2)
Alkaloids Derived from Polyketides
60(4)
The Use of Isotopes in the Elucidation of Biosynthetic Pathways
64(3)
The Shikimic Acid Pathway
67(24)
Introduction
68(2)
Transamination
70(2)
Biosynthesis of Natural Products Derived from Cinnamic Acid
72(6)
Lignans
78(2)
Biosynthesis of Alkaloids
80(11)
Decarboxylation of Amino Acids and α-Keto Acids
80(2)
Pictet--Spengler Reaction
82(1)
Alkaloids Derived from Tryptophan
82(4)
Alkaloids Derived from Tyrosine
86(5)
Terpenes
91(20)
What are Terpenes?
92(2)
Carbocations as Intermediates in Terpene Biosynthesis
94(4)
Hydride Shifts
94(1)
Alkyl Shifts
95(1)
Cyclizations
96(2)
Termination of Carbocations
98(2)
Loss of a Proton
98(1)
Addition of Water
98(2)
Terpene Biosynthesis
100(11)
Biosynthesis Initiated by Heterolysis of Pyrophosphates
100(6)
Biosynthesis from `Dimers' of Pyrophosphates
106(2)
Biosynthesis Initiated by Protonation or Epoxidation of an Alkene
108(3)
Natural Products Derived from Amino Acids
111(10)
Alkaloids
112(4)
Penicillins and Related Compounds
116(2)
Macrocyclic Peptides
118(1)
Porphyrins
119(2)
Answers to Problems
121(16)
Further Reading
137(2)
Index 139

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