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Questions and Answers
What is the primary function of lipids in biological membranes?
What is the primary function of lipids in biological membranes?
Which of the following is NOT a feature of amino acids?
Which of the following is NOT a feature of amino acids?
Which of the following interactions is NOT involved in the binding of naproxen to its protein target?
Which of the following interactions is NOT involved in the binding of naproxen to its protein target?
What is a key difference between DNA and RNA?
What is a key difference between DNA and RNA?
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Which of the following correctly describes the role of the R group in amino acids?
Which of the following correctly describes the role of the R group in amino acids?
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What are the four main classes of biomolecules?
What are the four main classes of biomolecules?
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What type of isomerism is present in carbohydrates, specifically when referring to diastereomers?
What type of isomerism is present in carbohydrates, specifically when referring to diastereomers?
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Which of the following is a key feature of steroids?
Which of the following is a key feature of steroids?
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Which of the following statements accurately describes enantiomers?
Which of the following statements accurately describes enantiomers?
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What is the key characteristic that distinguishes chiral molecules from achiral molecules?
What is the key characteristic that distinguishes chiral molecules from achiral molecules?
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Which of the following terms is used to describe molecules that are different across a plane of symmetry but have the same parts?
Which of the following terms is used to describe molecules that are different across a plane of symmetry but have the same parts?
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Which of the following statements accurately describes the relationship between enantiomers and diastereomers?
Which of the following statements accurately describes the relationship between enantiomers and diastereomers?
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Why are sp3 hybridized carbons with two identical substituents considered achiral and not stereocenters?
Why are sp3 hybridized carbons with two identical substituents considered achiral and not stereocenters?
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Which of the following statements accurately describes the term 'stereocenter'?
Which of the following statements accurately describes the term 'stereocenter'?
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What is the significance of the 'R' and 'S' designations in stereochemistry?
What is the significance of the 'R' and 'S' designations in stereochemistry?
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Which of the following describes how the term DIASTEREOMERS relates to the Greek word roots?
Which of the following describes how the term DIASTEREOMERS relates to the Greek word roots?
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What is the key factor that distinguishes enantiomers?
What is the key factor that distinguishes enantiomers?
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What is a racemic mixture?
What is a racemic mixture?
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Which of the following is NOT a characteristic of diastereomers?
Which of the following is NOT a characteristic of diastereomers?
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Which of the following molecules can exist as diastereomers?
Which of the following molecules can exist as diastereomers?
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What is the relationship between enantiomers and proteins?
What is the relationship between enantiomers and proteins?
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How can you distinguish between enantiomers?
How can you distinguish between enantiomers?
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What is the significance of the (R) and (S) designations for enantiomers?
What is the significance of the (R) and (S) designations for enantiomers?
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What is the approximate age of the technology that allows for the production of single enantiomers of drugs?
What is the approximate age of the technology that allows for the production of single enantiomers of drugs?
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A molecule with two stereocenters will have how many sets of enantiomers?
A molecule with two stereocenters will have how many sets of enantiomers?
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Which of the following statements about enantiomers is TRUE?
Which of the following statements about enantiomers is TRUE?
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What is the requirement for an sp3 tetrahedral carbon to be a stereocenter?
What is the requirement for an sp3 tetrahedral carbon to be a stereocenter?
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What is the definition of a racemic mixture?
What is the definition of a racemic mixture?
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What is the difference between an enantiomer and a diastereomer?
What is the difference between an enantiomer and a diastereomer?
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What is the primary difference between triglycerides and phospholipids?
What is the primary difference between triglycerides and phospholipids?
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What makes phospholipids ideal for forming cell membranes?
What makes phospholipids ideal for forming cell membranes?
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What is the role of esterification in the formation of triglycerides?
What is the role of esterification in the formation of triglycerides?
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Which of the following statements correctly describes a key difference between the structure of triglycerides and phospholipids?
Which of the following statements correctly describes a key difference between the structure of triglycerides and phospholipids?
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What is the primary function of triglycerides in biological systems?
What is the primary function of triglycerides in biological systems?
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What type of interaction is responsible for the formation of a lipid bilayer?
What type of interaction is responsible for the formation of a lipid bilayer?
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What property of phospholipids allows them to form a bilayer membrane?
What property of phospholipids allows them to form a bilayer membrane?
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How does the structure of a phospholipid contribute to the formation of cell membranes?
How does the structure of a phospholipid contribute to the formation of cell membranes?
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What is one of the primary functions of carbohydrates in the body?
What is one of the primary functions of carbohydrates in the body?
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Which statement correctly describes nucleotides?
Which statement correctly describes nucleotides?
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What are the main components of a nucleotide?
What are the main components of a nucleotide?
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Which carbohydrate is involved in the medium-term energy storage in the body?
Which carbohydrate is involved in the medium-term energy storage in the body?
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What distinguishes ribose from deoxyribose in their structures?
What distinguishes ribose from deoxyribose in their structures?
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What type of molecule is formed when nucleotides bond together?
What type of molecule is formed when nucleotides bond together?
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In what forms should ribose and deoxyribose be recognized?
In what forms should ribose and deoxyribose be recognized?
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Which function does ATP serve beyond being part of nucleic acids?
Which function does ATP serve beyond being part of nucleic acids?
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Flashcards
Stereochemistry
Stereochemistry
The study of spatial arrangements of atoms in molecules.
Conformational Isomer
Conformational Isomer
Isomers that differ in the rotation around single bonds.
Chirality
Chirality
The property of a molecule having non-superimposable mirror images.
Enantiomers
Enantiomers
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Racemic Mixture
Racemic Mixture
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sp3 stereocenters
sp3 stereocenters
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Achiral
Achiral
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Stereocenter
Stereocenter
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R and S configurations
R and S configurations
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Stereoisomers
Stereoisomers
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Diastereomers
Diastereomers
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Chiral Molecules
Chiral Molecules
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Chiral Light Interaction
Chiral Light Interaction
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Physical Properties of Diastereomers
Physical Properties of Diastereomers
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Biomolecules
Biomolecules
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Lipid Bilayers
Lipid Bilayers
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Amino Acids
Amino Acids
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Nucleotides
Nucleotides
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Carbohydrates
Carbohydrates
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Steroid Lipids
Steroid Lipids
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DNA vs. RNA
DNA vs. RNA
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Triglycerides
Triglycerides
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Esterification
Esterification
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Phospholipids
Phospholipids
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Hydrophobic Tails
Hydrophobic Tails
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Charged Polar Group
Charged Polar Group
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Intermolecular Forces
Intermolecular Forces
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Biological Membrane Function
Biological Membrane Function
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Energy Source
Energy Source
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Polysaccharides
Polysaccharides
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Nucleic Acids
Nucleic Acids
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Ribose
Ribose
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Deoxyribose
Deoxyribose
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Nucleobases
Nucleobases
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Study Notes
Lecture Information
- Course: PHAR 7813 Principles of Drug Action I
- Lecture: 5
- Topic: Understanding Drugs on the Molecular Level: Stereochemistry and Molecular Introduction to Biomolecules
- Date: January 31st, 2023
- Instructor: Anthony W. G. Burgett, Ph.D.
Learning Objectives: Stereochemistry
- Define stereochemistry, isomer, conformational isomer, substituents, and stereoisomers.
- Describe conformational isomers and their limitations in drug molecules.
- Identify sp² hybridized functional groups that can have multiple stereoisomers based on substituents.
- Identify requirements for an sp³ tetrahedral carbon to be a stereocenter.
- Define chirality, asymmetry, stereochemical configuration, enantiomers, and diastereomers.
- Identify possible stereochemical configurations around an sp³ stereocenter and name them.
- Explain why enantiomers have identical physical properties but different drug properties.
- Understand how a molecule with two stereocenters has two sets of enantiomers that are diastereomers to each other.
- Define and recognize a racemic mixture and its existence in a molecule based on its structure.
Learning Objectives: Biomolecules
- List and identify the four major classes of biomolecules based on their structure.
- Define the lipid class of biomolecules.
- Describe how lipids organize into bilayers and identify lipid classes.
- Identify steroids, fatty acid lipids, triglycerides, and phospholipids based on their structures.
- Define and recognize amino acids, peptides, and proteins.
- Identify the four parts of an amino acid.
- Explain why proteins can be considered to have stereochemistry.
- Define and recognize carbohydrates in open form, closed forms, 3D drawings, and polymeric forms (e.g., glucose, ribose).
- Recognize monosaccharides, disaccharides, and polysaccharides and their stereoisomer forms.
- Identify the three components that make up nucleotides and how they polymerize into nucleic acids (DNA and RNA).
- Recognize that nucleotides have biological activities besides forming DNA/RNA.
- Identify ribose and deoxyribose in open and closed forms and the 5 nucleobases (e.g., adenine, cytosine, thymine, uracil, guanine) related to nucleotides.
- Explain the molecular structural differences between DNA and RNA.
Understanding Drugs on the Molecular Level
- Stereochemistry greatly influences drug molecule form and function (illustrated with naproxen).
- The precise arrangement of atoms (stereochemistry) is vital for a drug to bind to its target protein.
- Different stereochemical configurations of a compound can lead to drastically different interactions with proteins, influencing drug effectiveness.
Organic Chemistry Review of Stereochemistry
- Isomers are different compounds with the same molecular formula.
- Stereoisomers have the same connectivity but different 3D arrangements.
- Constitutional isomers have different bonding patterns.
- Configurational isomers cannot be converted by rotating around single bonds (e.g., sp² carbons, alkane groups).
- Conformational isomers can be converted by rotating around single bonds.
- Enantiomers are nonsuperimposable mirror images.
- Diastereomers are stereoisomers that are not mirror images.
- Geometric Isomers (sp²) have no stereocenters; Optical Isomers (sp³) have stereocenters.
Understanding sp³ Chiral Stereocenters
- A molecule with an sp³ hybridized carbon atom with four different substituents is chiral.
- The four different configurations create two non-superimposable mirror images called enantiomers (denoted as R or S).
Diastereomers
- Diastereomers differ in configuration at two or more stereocenters.
- They have different properties because they are not mirror images and therefore are not enantiomers.
Racemic Mixture
- A racemic mixture contains equal amounts of both enantiomers of a chiral compound.
- The mixture shows squiggly lines between the chiral center and its substituents.
- Historically, this meant drug manufacturing did not focus on separate pure enantiomers but now there is increased focus on single enantiomer preparation due to vastly different therapeutic effects.
Molecular Introduction to Biomolecules
- Major biological molecules include nucleic acids (DNA and RNA), proteins, carbohydrates, and lipids.
- Lipids are categorized by their features and poor aqueous solubility.
- Main types of molecules of Lipids are: triglycerides, fatty acids, phospholipids, and steroids.
- Nucleic acids consist of nucleotides.
- Proteins are polymers of amino acids.
- Carbohydrates can be monosaccharides, disaccharides, or polysaccharides.
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Description
Test your knowledge on fundamental concepts in biochemistry, including the functions of lipids, amino acids, biomolecule classes, and the differences between DNA and RNA. This quiz covers essential topics every student in the field should know, such as isomerism and molecular interactions. Challenge yourself and see how well you understand these key biochemical principles!