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Bioorganic synthesis : an introduction /
Building on the foundation of a one-year introductory course in organic chemistry, Bioorganic Synthesis: An Introduction focuses on organic reactions involved in the biosynthesis of naturally-occurring organic compounds with special emphasis on natural products of pharmacological interest. The book...
| Clasificación: | Libro Electrónico |
|---|---|
| Autor principal: | |
| Formato: | Electrónico eBook |
| Idioma: | Inglés |
| Publicado: |
New York, NY :
Oxford University Press,
[2016]
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| Temas: | |
| Acceso en línea: | Texto completo |
Tabla de Contenidos:
- Note continued: Study Problems
- Why We Synthesize Organic Compounds
- Synthetic Challenges: Total Synthesis
- Synthetic Challenges: Semisynthesis
- Synthetic Challenges: Biomimetic Synthesis
- Synthetic Challenges: Structural Revision or Confirmation
- Synthetic Challenges: Formal Synthesis
- Synthetic Challenges: Stereoselective Synthesis of Optically Pure Compounds
- Resolution of Enantiomers to Obtain Optically Pure Compounds
- Use of Chiral Pool Compounds for Synthesis of Optically Pure Natural Products
- Use of Chiral Reagents for Synthesis of Optically Pure Compounds
- Use of Chiral Substrate Control for Stereoselective Synthesis
- Use of Chiral Auxiliaries for Synthesis of Optically Pure Compounds
- Use of Chiral Catalysis for Synthesis of Optically Pure Compounds
- Use of Enzymes for Synthesis of Optically Pure Compounds: Biocatalysis
- Some Final Thoughts
- Study Problems.
- Machine generated contents note: The Unique Role of Carbon
- Distinguishing Primary Versus Secondary Metabolism
- Secondary Metabolites and Natural Products
- Natural Products in Organic Chemistry and Medicine
- The Organic Chemistry of Biosynthesis
- Goals and Structure of This Book
- Review of Functional Groups, Stereochemistry, and Conformational Analysis
- Prochiral Relationships: One Step from Chirality
- Prochiral it-Systems: "Two-Faced" Reaction Centers
- Diastereotopic Atoms and Groups: One Step from a Diasteroeomer
- Monosubstituted Cyclohexanes: Favoring Equatorial Positions
- Disubstituted Cyclohexanes: Equivalent and Nonequivalent Combinations
- Bicyclic Systems: Joining of Rings
- Heterocyclic Ring Systems: One Atom Makes All the Difference
- Bond Making and Breaking: Have Pair, Will Share; Need Two from You
- Bronsted Acid-Base Reactions: Proton Donors Gladly Accepted
- Acidity Trends: Why that Proton Is or Isn't Acidic
- Carbocations: Three Bonds to Carbon Can Be a Plus
- Radicals: Odd and Reactive
- Elimination Reactions: Introducing the Carbon-Carbon n-Bond
- Carbocations: Rearrangements and Fates
- Electrophilic Additions: n-Bonds as Nucleophilic Agents
- Nucleophilic Substitutions and Alkylations: Make or Break for C-X Bonds
- Nucleophilic Carbonyl Addition Reactions: C=O n-Bond under Attack
- Imine Formation: Making the Essential C=N Linkage
- Nucleophilic 1,4-(Conjugate) Addition Reactions: Remote Attack on Conjugated Carbonyls
- Nucleophilic Acyl Substitution Reactions: Turning One Acyl Compound into Another
- Looking Ahead
- Study Problems
- Enzymes: The Catalysts of Biological Organic Chemistry
- Cofactors: Enzyme Assistants in Bioorganic Reactions
- NADH/NADPH: Nature's Version of Sodium Borohydride for Carbonyl Reduction
- NAD+/NADP+: Nature's Version of PCC for Alcohol Oxidation
- FAD: Another Hydride Acceptor for Dehydrogenations
- Monooxygenases: Special Delivery of One 0 atom from 02
- Dioxygenases: Delivering Both 0 Atoms from 02
- Other Oxidations: Hydroquinone and Catechol Oxidations
- Amine Oxidations: From Imines to Carbonyl Compounds and Beyond
- PLP: Transamination and Decarboxylation of Amino Acids
- Other Important Decarboxylations: 13-Keto Acids, o- and p-Hydroxybenzoic Acids
- Thiamine Diphosphate (TPP) and Lipoic Acid: Decarboxylation and Acyl Transfer
- Biotin: The CO2 Carrier, Transport, and Transfer Agent
- SAM: A C1 Fragment for Methyl Groups
- DMAPP: An Allylic C, Fragment for Structure Building
- Other Essential Structural Fragments: Putting it All Together
- Looking Ahead
- Study Problems
- What Makes a Carbohydrate?
- Cyclic Hemiacetals and Anomers
- C-2 Epimers and Enediols[--]Simple Conversion of One Carbohydrate into Another
- Other Important Monosaccharides: Deoxy and Amino Sugars
- The Significance of the Anomeric Carbon: Glycoside Formation
- UDP-Sugars and Glycoside Formation: SN2 Chemistry at Work
- Organic Reactions in Carbohydrate Chemistry: Overview of Glucose Metabolism
- Glycolysis: A 10-Step Program
- What Happens to the Pyruvic Acid from Glycolysis
- The Citric Acid Cycle: Another 10-Step Program
- The Pentose Phosphate Pathway: Seven Alternative Steps to Some Familiar Intermediates
- The Big Picture
- Amino Acids: More Important Primary Metabolite Building Blocks for Biosynthesis
- Biosynthesis of Serine: A Good Place to Start
- Peptides and Proteins: A Very Brief Review
- Putting Proteins and Carbohydrates Together: Glycoproteins Versus Protein Glycosylation
- Looking Ahead
- Study Problems
- Classification of Terpenes: How Many Isoprene Units?
- The Mevalonic Acid Route to DMAPP and IPP
- The Deoxyxylulose Phosphate Route to IPP and DMAPP
- Hemiterpenes: Just One Isoprene Unit
- Monoterpenes (C10) and Isoprene Linkage: Heads, IPP Wins; Tails, DMAPP Loses
- Geranyl PP to Neryl PP via Linalyl PP: The Importance of Alkene Stereochemistry
- Some Acyclic Monoterpenes and Their Uses
- Mono- and Bicyclic Monoterpenes via Cationic Cyclizations and Wagner-Meerwein Shifts
- What's that Smell? Limonene Derivatives as Flavor and Fragrance Compounds
- Irregular Monoterpenes: If Not Head-to-Tail, then How?
- Iridoids: From Catnip to Alkaloids
- Sesquiterpenes (C15): Linking of Different Starter Units
- Some FPP Cyclizations in Sesquiterpene Biosynthesis
- Trichodiene and the Trichothecenes: How to Trace a Rearrangement Pathway
- Diterpenes (C20): Taking it to the Next Level of Molecular Complexity and Diversity
- Cyclic Diterpenes: From Baseball and Plant Hormones to Anticancer Drugs
- Sesterterpenes (C25): Less Common, More Complex
- Triterpenes and Steroids: Another Case of Irregular Linkage of Terpene Units
- Oxidosqualene and Steroid Biosynthesis: Cyclization to Lanosterol and Beyond
- Conversion of Lanosterol (C30) to Cholesterol (C27): Where Did the Carbons Go?
- Conversions of Cholesterol: Production of the Sex Hormones
- Dehydrocholesterol, Sunshine, and Vitamin D3 Biosynthesis
- Tetraterpenes and Carotenoids: Tail-to-Tail Linkage of C20 Units
- Looking Ahead
- Study Problems
- Fatty Acids: Multiples of Two Carbons, Saturated or Unsaturated
- Saturated Fatty Acid Biosynthesis: It All Starts with Acetyl-CoA
- Branched Fatty Acids: Different Routes and Different Results
- Mono- and Polyunsaturated Fatty Acids: Putting in the "Essential" Double Bonds
- Aerobic Versus Anaerobic Routes to Desaturation
- Further Desaturation of Fatty Acids: Triple Bonds and Rings
- Prostaglandins, Thromboxanes, and Leukotrienes: The Power of Oxygenated FAs
- Polyketide Biosynthesis: More Starter Units and Extender Units, but with a Twist
- Aromatic Polyketide Natural Products: Phenols and Related Structures
- Isotopic Labeling Studies: Biosynthetic Insights via 13C NMR
- Further Modification of Polyketides: Alkylations, Oxidations, Reductions, and Decarboxylations
- Other Oxidative Modifications of Aromatic Rings: Expansion or Cleavage Processes
- Oxidative Coupling of Phenols: Formation of Aryl-Aryl Bonds
- The Use of Other Starter Groups: From Cancer Drugs and Antibiotics to Poison Ivy
- More on Polyketide Synthase (PKS) Systems: Increasing Product Diversity
- Modular Type I PKS Complexes and Macrolide Antibiotics: Erythromycin Biosynthesis
- Genetic Manipulation of Modular PKS Systems: Rational Drug Modification
- Some Final PKS Products of Medicinal Importance
- Looking Ahead
- Study Problems
- What Is Shikimic Acid?
- Shikimic, Chorismic, and Prephenic Acids at the Heart of the Pathway
- The Claisen Rearrangement: Allyl Vinyl Ethers in a Chair
- Conversion of Chorismic Acid to Prephenic Acid
- Conversion of Prephenic Acid to Phenylalanine or Tyrosine
- More Uses for Chorismic Acid
- Shikimic Acid Pathway Products from Phenylalanine and Tyrosine: An Overview
- Phenylpropanoids: A Large Family of Phenyl C3 Compounds
- Phenylpropanoids: Reduction of Acids to Phenyl C3 Aldehydes and Alcohols
- Reduction of Phenyl C3 Alcohols to Phenylpropenes
- Lignans and Lignin: Oxidative Phenolic Coupling with a Twist
- Coniferyl Alcohol Oxidative Coupling: Allyl C-Radical + Allyl C-Radical
- Coniferyl Alcohol Oxidative Coupling: Ortho C-Radical + Allyl C-Radical
- Coniferyl Alcohol Oxidative Coupling: O-Radical + Allyl C-Radical
- Lignin: A Plant Polymer and Major Source of Carbon
- Podophyllotoxin Biosynthesis: Aryltetralin Lignans from the American Mayapple
- Cleavage of Cinnamic Acids to Phenyl Cl Compounds: Different Routes, Similar Outcomes
- Coumarins: Sweet-Smelling Benzopyrones
- Mixed Products: Combining the Shikimate, Polyketide, and Terpenoid Pathways
- Kavalactones: Natural Sedatives from the South Pacific
- Flavonoids: Structurally Diverse Plant Polyphenolics
- The Chalcone-to-Flavanone-to-Flavone Sequence: Formation of Apigenin
- The Flavanone-to-Dihydroflavonol-to-Anthocyanin Sequence: Formation of Pelargonidin
- The Flavanone-to-Isoflavanone-to-Isoflavone Sequence: Formation of Genistein
- Isoflavanoid Structural Modifications: Production of Antimicrobial Phytoalexins
- Rotenoids: Fish Poisons from Isoflavones
- Looking Ahead
- Study Problems
- Alkaloid Structure: The Importance of N-Heterocycles
- Alkaloids Not Derived from Amino Acids: Amination Reactions, Poisons, and Venoms
- Amino Acids and Mannich
- Reactions: Important Keys to Alkaloid Biosynthesis
- Alkaloids from Ornithine: Tropanes via the Mannich Reaction in Action
- Pyrrolizidine Alkaloids: Poison Plants and Insect Defense
- Piperidine-Type Alkaloids Derived from Lysine
- Quinolizidine Alkaloids: Livestock Poisons from Cadaverine
- Alkaloids from Phenylalanine: From Neurotransmitters to Decongestants and Narcotics
- Alkaloids from Tyrosine: The Pictet-Spengler Reaction in Alkaloid Biosynthesis
- (S)-Reticuline: A Versatile Pictet-Spengler-Derived Benzyltetrahydroisoquinoline
- Oxidative Coupling in Alkaloid Biosynthesis: Biosynthesis of Corytuberine and Morphine
- The Morphine Rule
- Alkaloids from Tryptophan: Adventures in Indole Alkaloid Structural Complexity
- Pictet-Spengler-Type Reactions of Tryptamine: p-Carbolines and Indole Terpene Alkaloids
- Alkaloids from Nicotinic Acid: Toxic Addictive Derivatives of a Common Nutrient
- Alkaloids from Anthranilic Acid: From Tryptophan to Quinolines and Acridines
- Alkaloids from Histidine: From Simple Amides to Glaucoma Drugs
- Purine Alkaloids: Addictive Stimulants in our Coffee, Tea, and Chocolate
- Cyclic and Macrocyclic Peptides: From Sweeteners to Antibiotics and Beyond
- Penicillins, Cephalosporins, and Carbapenums: The Essential p-Lactam Antibiotics
- A Final Look Ahead.