Domanda del libro di testo
Two of the 20 common amino acids have two chiral carbon atoms in their structures. Identify these amino acids and their chiral carbon atoms.
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Ch.18 Amino Acids and Proteins
McMurry8th EditionFundamentals of General, Organic, and Biological ChemistryISBN: 9780134015187
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TOC.tableOfContents
- Ch.1 Matter and Measurements27
- Ch.2 Atoms and the Periodic Table20
- Ch.3 Ionic Compounds8
- Ch.4 Molecular Compounds23
- Ch.5 Classification & Balancing of Chemical Reactions12
- Ch.6 Chemical Reactions: Mole and Mass Relationships28
- Ch.7 Chemical Reactions: Energy, Rate and Equilibrium64
- Ch.8 Gases, Liquids and Solids24
- Ch.9 Solutions52
- Ch.10 Acids and Bases25
- Ch.11 Nuclear Chemistry22
- Ch.12 Introduction to Organic Chemistry: Alkanes57
- Ch.13 Alkenes, Alkynes, and Aromatic Compounds47
- Ch.14 Some Compounds with Oxygen, Sulfur, or a Halogen50
- Ch.15 Aldehydes and Ketones45
- Ch.16 Amines42
- Ch.17 Carboxylic Acids and Their Derivatives57
- Ch.18 Amino Acids and Proteins82
- Ch.19 Enzymes and Vitamins63
- Ch.20 Carbohydrates44
- Ch.21 The Generation of Biochemical Energy65
- Ch.22 Carbohydrate Metabolism45
- Ch.23 Lipids42
- Ch.24 Lipid Metabolism33
- Ch.25 Protein and Amino Acid Metabolism24
- Ch.26 Nucleic Acids and Protein Synthesis45
McMurry8th EditionFundamentals of General, Organic, and Biological ChemistryISBN: 9780134015187Non è quello che usi tu?Cambia libro di testo
Capitolo 18, Problema 10
Is serine chiral? Draw serine and identify the chiral atom. Explain why serine is chiral.
Guida verificata passo dopo passo1
Step 1: Begin by understanding the structure of serine. Serine is an amino acid with the molecular formula C₃H₇NO₃. It contains an amino group (-NH₂), a carboxyl group (-COOH), a hydroxyl group (-OH), and a side chain with a single hydrogen atom attached to the central carbon atom.
Step 2: Draw the structure of serine. Place the central carbon atom (called the alpha carbon) at the center. Attach the amino group (-NH₂), the carboxyl group (-COOH), the hydroxyl group (-OH), and a hydrogen atom to the alpha carbon. Ensure that the groups are arranged tetrahedrally around the alpha carbon.
Step 3: Identify the chiral center. A chiral center is a carbon atom that is bonded to four different groups. In serine, the alpha carbon is bonded to four distinct groups: the amino group (-NH₂), the carboxyl group (-COOH), the hydroxyl group (-OH), and a hydrogen atom.
Step 4: Explain why serine is chiral. Since the alpha carbon in serine is bonded to four different groups, it lacks a plane of symmetry and cannot be superimposed on its mirror image. This property makes serine a chiral molecule.
Step 5: Conclude by noting that the presence of a chiral center in serine means it can exist as two enantiomers (non-superimposable mirror images), which are designated as L-serine and D-serine based on their spatial arrangement.
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Chirality
Chirality refers to the geometric property of a molecule that makes it non-superimposable on its mirror image. A chiral molecule typically has at least one carbon atom bonded to four different substituents, creating two distinct forms known as enantiomers. This property is crucial in biochemistry, as the different enantiomers can have vastly different biological activities.
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Percorso guidato
1:39
Chirality Example 1
Amino Acids
Amino acids are organic compounds that serve as the building blocks of proteins. Each amino acid consists of a central carbon atom (the alpha carbon) bonded to an amino group, a carboxyl group, a hydrogen atom, and a variable side chain (R group). The structure and properties of the side chain determine the characteristics of the amino acid, including its chirality.
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Percorso guidato
3:03Amino Acid Catabolism: Amino Group Example 2
Serine Structure
Serine is a polar amino acid with the chemical formula C3H7NO3. Its structure includes a central carbon atom bonded to an amino group, a carboxyl group, a hydrogen atom, and a hydroxymethyl side chain (-CH2OH). The presence of four different groups attached to the alpha carbon makes serine chiral, allowing it to exist in two enantiomeric forms.
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1:01Structural Formula Concept 2
Pratica correlata
Domanda del libro di testo
Valine is an amino acid with a nonpolar side chain and serine is one with a polar side chain. Draw the two amino acids.
a. Why is the side chain for valine nonpolar, whereas the side chain for serine is polar?
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Domanda del libro di testo
Draw the structure of glutamic acid at low pH, at high pH, and at the two forms that exist between low pH and high pH. Which of these structures represents the zwitterion?
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Domanda del libro di testo
Which amino acid is hydrophilic (dissolves in aqueous solutions)? Why?
a. isoleucine
b. phenylalanine
c. aspartic acid
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Domanda del libro di testo
Valine is an amino acid with a nonpolar side chain, and serine is an amino acid with a polar side chain. Draw the two dipeptides that can be formed by these two amino acids. Identify the peptide bond.
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Domanda del libro di testo
Using Table 18.3, name the α-amino acids that (a) contain an aromatic ring, (b) contain sulfur, (c) are alcohols, and (d) have alkyl-group side chains.
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