Michael B. Smith - Biochemistry_ An Organic Chemistry Approach-CRC Press Inc (2020)

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Half Title	#2,0,-32767Title Page	#4,0,-32767Copyright Page	#5,0,-32767Table of Contents	#6,0,-32767Preface	#12,0,-32767Author
Common Abbreviations
1 Fundamental Principles of Organic Chemistry
	1.1 Bonding and Orbitals
	1.2 Ionic versus Covalent Chemical Bonds
	1.3 Breaking Covalent Bonds
	1.4 Polarized Covalent σ-Bonds
	1.5 Reactive Intermediates
	1.6 Alkanes and Isomers
	1.7 The IUPAC Rules of Nomenclature
	1.8 Rings Made of Carbon: Cyclic Compounds
	1.9 Hydrocarbon Functional Groups
	1.10 Heteroatom Functional Groups
		1.10.1 C—X Type Functional Groups
		1.10.2 C=X Type Functional Groups
	1.11 Hydrogen-Bonding and Solubility
	1.12 Rotamers and Conformation
	1.13 Conformations with Functional Groups
	1.14 Conformation of Cyclic Molecules
	1.15 Stereogenic Carbons and Stereoisomers
	1.16 Absolute Configuration [(R) and (S) Nomenclature]
	1.17 Specific Rotation
	1.18 Diastereomers
	1.19 Alkene Stereoisomers: (E) and (Z)-Isomers
	Homework
2 The Importance of Water in Biochemical Systems
	2.1 Hydrogen Bonding
	2.2 Solubility
	2.3 Water Molecules in Biological Systems
	2.4 Acid-Base Equilibria in Water
	2.5 Buffers
	2.6 Structural Features That Influence Acid Strength
	2.7 Acid and Base Character of Alcohols, Thiols, Amines and Carbonyls
		2.7.1 Acids
		2.7.2 Bases
	2.8 Elimination Reactions of Alkyl Halides (E2 and E1 Reactions)
	2.9 Acid-Base Equilibria in Amino Acids
	2.10 Directionality
	Homework
3 Nucleophiles and Electrophiles
	3.1 Nucleophiles and Bimolecular Substitution (the SN2 Reaction)
	3.2 Nucleophilic Substitution with Alcohols, Ethers, Amines, or Phosphines
	3.3 Carbocations and the SN1 Reaction
	3.4 Ethers and Thioethers as Nucleophiles
	3.5 Chemical Reactions of Carbonyl Groups
	3.6 Biochemical Reactions of Ketones and Aldehydes
	3.7 Carboxylic Acid Derivatives and Acyl Substitution
	3.8 Biological Hydrolysis
	Homework
4 Radicals
	4.1 Structure of Radicals
	4.2 Formation of Radicals in Organic Chemistry
	4.3 Reactions of Radicals
	4.4 Formation of Radicals in Biological Systems
	4.5 Radicals in Biological Systems
	4.6 Radical Reactions in Biochemical Systems
	4.7 Radicals and Cancer
	Homework
5 Dienes and Conjugated Carbonyl Compounds in Biochemistry
	5.1 Conjugated Dienes and Conjugated Carbonyl Compounds
	5.2 Reactions of Conjugated Compounds
	5.3 Conjugate (Michael) Addition
	5.4 Enzyme-Mediated Conjugate Additions
	5.5 Sigmatropic Rearrangement Reactions
	5.6 Enzyme-Mediated Sigmatropic Rearrangements
	Homework
6 Enolates and Enolate Anions
	6.1 Aldehydes and Ketones Are Weak Acids
	6.2 Formation of Enolate Anions
	6.3 The Aldol Condensation
	6.4 Enzyme-Mediated Aldol Condensations
	6.5 The Claisen Condensation
	6.6 Enzyme-Mediated Claisen Condensation
	6.7 Decarboxylation
	Homework
7 Enzymes
	7.1 Enzyme Kinetics
		7.1.1 Kinetics in Organic Chemistry
		7.1.2 Catalysts and Catalytic Reactions
		7.1.3 Enzyme Kinetics
	7.2 Enzymes and Enzyme Classes
	7.3 Oxidoreductases (EC 1)
		7.3.1 Chemical Oxidation of Alcohols
		7.3.2 Oxidases
		7.3.3 Chemical Reduction of Carbonyl Compounds
		7.3.4 Reductases
	7.4 Transferases (EC 2)
		7.4.1 Chemical Reactions That Incorporate Methyl, Hydroxyl, Glycosyl or Amino Groups into New Molecules
		7.4.2 Methyl, Hydroxyl, Thiol, and Glycosyl Transferases
	7.5 Hydrolyases (EC 3)
		7.5.1 Chemical Hydrolysis
		7.5.2 Esterases
		7.5.3 Other Hydrolyases
	7.6 Lyases (EC 4)
		7.6.1 Bond Cleavage in Organic Chemistry
			7.6.1.1 Decarboxylation
			7.6.1.2 Enol Formation and the Acid-Catalyzed Aldol
			7.6.1.3 Dehydration Reactions
			7.6.1.4 [2+2]-Photocycloaddition
		7.6.2 Lyase Reactions
	7.7 Isomerases (EC 5)
		7.7.1 Chemical Isomerization Reactions
		7.7.2 Isomerase Reactions
	7.8 Ligases (EC 6)
		7.8.1 Chemical Methods for Carboxylation and Nucleotide Synthesis
			7.8.1.1 Reactions with Carbon Dioxide
			7.8.1.2 Synthesis of Polynucleotides and Polynucleosides
		7.8.2 Enzymatic Coupling
	7.9 Translocases (EC 7)
		7.9.1 Enzymatic Transport Reactions
		7.9.2 Transport of Organic Materials
	Homework
8 Lipids
	8.1 Carboxylic Acids and Esters
	8.2 Nitrate Esters, Sulfate Esters, and Phosphate Esters
	8.3 Lipid Classes
	8.4 Chemical Synthesis of Esters
	8.5 Biosynthesis and Biodegradation of Esters
	Homework
9 Aromatic Compounds and Heterocyclic Compounds
	9.1 Benzene and Aromaticity
	9.2 Benzene Is a Carcinogen
	9.3 Functionalized Benzene Derivatives
	9.4 Electrophilic Aromatic Substitution: The SEAr Reaction
	9.5 Enzymatic SEAr Reactions
	9.6 Reduction of Aromatic Compounds
	9.7 Biological Reduction of Aromatic Rings
	9.8 Nucleophilic Aromatic Substitution. The SNAr Reaction
	9.9 Enzymatic SNAr Reactions
	9.10 Polynuclear Aromatic Hydrocarbons
	9.11 Heteroaromatic Compounds: Nitrogen, Oxygen, or Sulfur
	9.12 Reactions of Heteroaromatic Compounds
	9.13 Enzymatic Reactions That Generate Heterocyclic Compounds
	9.14 Reduced Forms of Nitrogen, Oxygen, and Sulfur Heterocycles
	9.15 Heteroaromatic Compounds with More Than One Ring
	Homework
10 Carbon–Metal Bonds, Chelating Agents and Coordination Complexes
	10.1 Organometallics
	10.2 Organometallics in Organic Chemistry
	10.3 Biologically Relevant Metals
	10.4 Chelating Agents
	Homework
11 Amino Acids
	11.1 Characteristics of Amino Acids
	11.2 Structure of α-Amino Acids
	Homework
12 Peptides and Proteins
	12.1 Reactions and Synthesis of α-Amino Acids
	12.2 Amino Acid Biosynthesis
	12.3 Peptides Are Poly(amides) of Amino Acid Residues
	12.4 Chemical Synthesis of Peptides
	12.5 Peptide Biosynthesis
	12.6 Proteins and Enzymes Are Poly(peptides)
	12.7 Peptide Degradation and End Group Identification
	12.8 Peptidases
	Homework
13 Carbohydrates
	13.1 (Poly)hydroxy Carbonyl Compounds
	13.2 Monosaccharides
	13.3 Mutarotation
	13.4 The Anomeric Effect
	13.5 Ketose Monosaccharides
	Homework
14 Glycosides
	14.1 Monosaccharides
	14.2 Disaccharides, Trisaccharides, Oligosaccharides, and Polysaccharides
	14.3 Reactions of Carbohydrates
	14.4 Biologically Important Glycosides
	14.5 Biosynthesis of Carbohydrates and Glycosides
	14.6 Biodegradation of Carbohydrates and Glycosides
	Homework
15 Nucleic Acids, Nucleosides and Nucleotides
	15.1 Nucleosides and Nucleotides
	15.2 Polynucleotides
	15.3 Chemical Synthesis of Nucleotides
	15.4 Biosynthesis of Nucleotides
	15.5 Ribozymes
	15.6 Hydrolysis of RNA and DNA
	15.7 RNA-Mediated Programmable DNA Cleavage
	15.8 Restriction Enzymes
	Homework
16 Answers to Homework Problems
	Chapter 1
	Chapter 2
	Chapter 3
	Chapter 4
	Chapter 5
	Chapter 6
	Chapter 7
	Chapter 8
	Chapter 9
	Chapter 10
	Chapter 11
	Chapter 12
	Chapter 13
	Chapter 14
	Chapter 15