Textbook Question
Two stereoisomers are obtained from the reaction of cyclopentene oxide and dimethylamine. The R,R-isomer is used in the manufacture of eclanamine, an antidepressant. What other isomer is obtained?
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Ch. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
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Table of contents
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 1)31
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 2)65
- Ch. 2 - Acids and Bases: Central to Understanding Organic Chemistry84
- Ch. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and Structure183
- Ch. 4 - Isomers: The Arrangement of Atoms in Space121
- Ch. 5 - Alkenes: Structure, Nomenclature, and an Introduction to Reactivity • Thermodynamics and Kinetics83
- Ch. 6 - The Reactions of Alkenes • The Stereochemistry of Addition Reactions175
- Ch. 7 - The Reactions of Alkynes • An Introduction to Multistep Synthesis119
- Ch. 8 - Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction to the Reactions of Benzene148
- Ch. 9 - Substitution and Elimination Reactions of Alkyl Halides212
- Ch. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds131
- Ch. 11 - Organometallic Compounds60
- Ch. 12 - Radicals90
- Ch. 13 - Mass Spectrometry; Infrared Spectroscopy; UV/Vis Spectroscopy62
- Ch. 14 - NMR Spectroscopy95
- Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives123
- Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives141
- Ch. 17 - Reactions at the Alpha-Carbon101
- Ch. 18 - Reactions of Benzene and Substituted Benzenes144
- Ch. 19 - More About Amines • Reactions of Heterocyclic Compounds49
- Ch. 20 - The Organic Chemistry of Carbohydrates80
- Ch. 21 - Amino Acids, Peptides, and Proteins57
- Ch. 22 - Catalysis in Organic Reactions and in Enzymatic Reactions35
- Ch. 23 - The Organic Chemistry of the Coenzymes—Compounds Derived from Vitamins1
- Ch. 28 - Pericyclic Reactions58
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Bruice 8th EditionCh. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing CompoundsProblem 97b
Bruice 8th EditionCh. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing CompoundsProblem 97bChapter 11, Problem 97b
Triethylenemelamine (TEM) is an antitumor agent. Its activity is due to its ability to cross-link DNA.
b. Explain why it can cross-link DNA.
Verified step by step guidance1
Step 1: Analyze the structure of Triethylenemelamine (TEM). TEM contains three aziridine rings attached to a triazine core. Aziridine rings are three-membered cyclic amines that are highly strained and reactive due to their small ring size.
Step 2: Understand the reactivity of aziridine rings. Aziridine rings are electrophilic and can undergo nucleophilic attack by groups such as amines or thiols present in DNA. This makes them capable of forming covalent bonds with DNA bases.
Step 3: Explain the mechanism of DNA cross-linking. TEM can react with two nucleophilic sites on DNA, such as guanine bases, through its aziridine rings. This leads to the formation of covalent bonds between two DNA strands or within the same strand, effectively cross-linking the DNA.
Step 4: Discuss the biological implications of DNA cross-linking. Cross-linking prevents DNA replication and transcription, which disrupts cellular processes and leads to cell death. This is why TEM is effective as an antitumor agent.
Step 5: Relate the structure to its function. The triazine core of TEM provides a stable scaffold for the reactive aziridine rings, ensuring that the molecule can interact with DNA effectively and exert its antitumor activity.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
DNA Cross-Linking
DNA cross-linking refers to the formation of covalent bonds between DNA strands, which can inhibit DNA replication and transcription. This process is crucial in the mechanism of action for certain antitumor agents, as it disrupts the normal function of DNA, leading to cell death. Cross-linking can occur through various chemical interactions, often involving electrophilic agents that react with nucleophilic sites on the DNA.
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DNA Double Helix Example 1
Electrophilicity
Electrophilicity is a chemical property of a species that describes its ability to accept electrons. In the context of DNA cross-linking, electrophilic compounds can react with nucleophilic sites on DNA, such as the nitrogen or oxygen atoms in the bases. Triethylenemelamine (TEM) and related compounds can act as electrophiles, facilitating the formation of cross-links that interfere with DNA function.
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Antitumor Mechanism of Action
The antitumor mechanism of action involves various strategies that cancer drugs employ to inhibit tumor growth. For agents like TEM, the primary mechanism is through the induction of DNA damage via cross-linking, which prevents cancer cells from successfully replicating their DNA. This leads to cell cycle arrest and apoptosis, making these agents effective in treating certain types of cancer.
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