Amino Acids and Functional Groups Quiz

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Questions and Answers

What functional groups are present in all a-amino acids?

  • Carboxyl group and phosphate group
  • Amino group and hydroxyl group
  • Carboxyl group and hydroxyl group
  • Amino group and carboxyl group (correct)

Which statement accurately describes proline among amino acids?

  • It is classified as a primary amino acid.
  • It is a secondary amino acid with a unique structure. (correct)
  • It has a simple hydrogen atom as its side chain.
  • It contains a carboxyl group but lacks an amino group.

What distinguishes different a-amino acids from each other?

  • The number of carbon atoms in their backbone
  • The presence of a carboxyl group
  • The structure of their R group (correct)
  • The type of amino group they contain

In what way does proline differ from other a-amino acids?

<p>It includes a secondary amino group. (C)</p> Signup and view all the answers

Which amino acid has a hydrogen atom as its side chain?

<p>Glycine (D)</p> Signup and view all the answers

What configuration is designated when the hydroxyl group is on the left in a Fischer projection?

<p>L configuration (D)</p> Signup and view all the answers

In a Fischer projection, if the hydroxyl group is on the right, what is the designation of that molecule?

<p>D (C)</p> Signup and view all the answers

Which amino acid configuration corresponds to L-glyceraldehyde?

<p>L (B)</p> Signup and view all the answers

For D-amino acids, where is the a-amino group located in a Fischer projection?

<p>Right side (D)</p> Signup and view all the answers

What is the reference carbon for determining the D and L configurations in amino acids?

<p>Alpha carbon (C)</p> Signup and view all the answers

How many absolute configurations can amino acids have?

<p>Two (A)</p> Signup and view all the answers

Which of the following amino acids is ribosomally incorporated into proteins in the L-configuration?

<p>Alanine (C)</p> Signup and view all the answers

What does the designation D refer to in molecular terms?

<p>The absolute configuration with the hydroxyl group on the right (B)</p> Signup and view all the answers

Which type of amino acids are commonly found in ribosomally synthesized proteins?

<p>L-amino acids (D)</p> Signup and view all the answers

What is the basis for the preference of L-amino acids over D-amino acids in proteins?

<p>The reason is not known (A)</p> Signup and view all the answers

Which system is most useful for describing the configuration of chiral compounds?

<p>RS System (B)</p> Signup and view all the answers

In the RS System, how is priority among substituents on a chiral carbon determined?

<p>By the atomic number of bonded atoms (B)</p> Signup and view all the answers

What type of antibiotics contain D-amino acids?

<p>Tetrapeptide antibiotics (A)</p> Signup and view all the answers

Which amino acid is used to illustrate the prioritization of groups around a chiral carbon?

<p>Alanine (A)</p> Signup and view all the answers

Which statement is true regarding D-amino acids?

<p>They are found in some peptide antibiotics (A)</p> Signup and view all the answers

Which factor does NOT influence the priority ranking in the RS system?

<p>Presence of double bonds (D)</p> Signup and view all the answers

What is true about enantiomers?

<p>They are the same compound, differing only in the direction they rotate polarized light. (A)</p> Signup and view all the answers

Which statement correctly describes diastereomers?

<p>They are different compounds with distinct names and properties. (A)</p> Signup and view all the answers

What distinguishes enantiomers from conformations?

<p>Enantiomers involve non-superimposable mirror images. (B)</p> Signup and view all the answers

What is an achiral amino acid?

<p>It exists only in one configuration. (B)</p> Signup and view all the answers

How does the DL system relate to amino acids?

<p>It links the configuration of amino acids to that of a sugar molecule. (D)</p> Signup and view all the answers

Which of the following statements is incorrect?

<p>Achiral molecules have unique chirality. (D)</p> Signup and view all the answers

What happens when the configuration of a molecule is altered?

<p>Covalent bonds are rearranged and broken. (D)</p> Signup and view all the answers

Which of these compounds is achiral?

<p>Glycine (B)</p> Signup and view all the answers

What units are used for the concentration of a sample in optical activity measurements?

<p>Grams per milliliter (B)</p> Signup and view all the answers

For a compound's specific rotation denoted as [α], what is the path length standardized to?

<p>1 decimeter (C)</p> Signup and view all the answers

Which notation indicates the use of a sodium lamp with a wavelength of 589 nm in optical activity measurements?

<p>D line (B)</p> Signup and view all the answers

What is the specific rotation value when the observed optical rotation is 0.671° with a concentration of 0.025 g/mL and path length of 0.5 dm?

<p>53.68° (D)</p> Signup and view all the answers

What defines standard (or proteinogenic) amino acids?

<p>They are incorporated into proteins ribosomically. (C)</p> Signup and view all the answers

How many different amino acids participate in protein synthesis?

<p>22 (D)</p> Signup and view all the answers

What type of acids are all standard amino acids classified as?

<p>L-α-amino acids (B)</p> Signup and view all the answers

Which of the following best describes the term 'specific rotation'?

<p>It is a standard measure of optical activity. (B)</p> Signup and view all the answers

Which amino acids contain hydroxyl groups in their side chains?

<p>Serine, Threonine, Tyrosine (A)</p> Signup and view all the answers

What type of group does arginine contain in its side chain?

<p>Aguanidinium group (A)</p> Signup and view all the answers

At neutral pH, which amino acids contain negatively charged groups?

<p>Aspartate and Glutamate (B)</p> Signup and view all the answers

Which amino acid has a side chain that contains a thiol group?

<p>Cysteine (C)</p> Signup and view all the answers

What distinguishes histidine's side chain from the others mentioned?

<p>It can be positively charged near neutral pH. (D)</p> Signup and view all the answers

Lysine and arginine are categorized under which type of amino acid based on their side chains?

<p>Amino (C)</p> Signup and view all the answers

What type of amino acids does serine belong to based on the nature of its side chain?

<p>Hydroxyl (C)</p> Signup and view all the answers

Which of the following amino acids does not have a charged polar side chain?

<p>Cysteine (D)</p> Signup and view all the answers

Flashcards

Amino Acids

Organic compounds that serve as building blocks for proteins, containing carbon, hydrogen, oxygen, and nitrogen.

R-group (Side Chain)

The group of atoms attached to the alpha carbon in an amino acid, determining its unique properties.

Alpha Carbon (α-carbon)

The carbon atom in an amino acid to which both the amino and carboxyl groups are attached.

α-Amino Acid

The functional group containing both the amino and carboxyl groups, found in all standard amino acids.

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Proline

An amino acid with a secondary amino group, making it unique compared to other amino acids.

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Enantiomers

Non-superimposable mirror images of a chiral molecule.

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Diastereomers

Stereoisomers that are not mirror images of each other. They have different properties.

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Absolute configuration

The specific spatial arrangement of atoms in a molecule. It determines its properties.

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DL System

A system to assign absolute configuration of a chiral molecule based on the stereochemistry of the 3-carbon aldose sugar glyceraldehyde.

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Chiral molecule

A type of stereoisomer that has a non-superimposable mirror image.

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Achiral molecule

A molecule that lacks a chiral center and does not have a non-superimposable mirror image.

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Chiral center

A carbon atom bonded to four different substituents.

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Conformation

The specific spatial arrangement of atoms in a molecule. It can be changed by rotation around bonds.

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Absolute Configuration (D & L)

The absolute configuration of a molecule's four substituents bonded to a chiral carbon, determined by the position of the hydroxyl group in a Fischer projection. 'L' configuration has the hydroxyl group on the left, while 'D' configuration has it on the right.

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Glyceraldehyde

A simple sugar molecule with three carbon atoms, used as a reference for determining the absolute configuration (D or L) of other chiral molecules.

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Fischer Projection

A projection formula representing a molecule in 2D, with the carbon chain drawn vertically and the substituents projected either horizontally or vertically. Useful for visualizing the relative positions of atoms/groups.

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Chiral Carbon

A carbon atom bonded to four different substituents, making it asymmetric and leading to the existence of stereoisomers.

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R-group

The chemical group responsible for the unique properties of an amino acid, attached to the alpha carbon.

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Alpha Carbon

The central carbon atom in an amino acid to which the amino group, carboxyl group, and R-group are attached.

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Specific Rotation [α]

Dividing observed rotation by path length and concentration; a unique property of a compound that describes its ability to rotate plane-polarized light.

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Chiral Compound

A molecule that contains a chiral center and can rotate polarized light. It has a non-superimposable mirror image.

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Specific Rotation [α]

The standard value for a compound's ability to rotate plane-polarized light under specific conditions (concentration of 1 g/mL, path length of 1 decimeter).

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Achiral Compound

A molecule that doesn't have a chiral center. It cannot rotate polarized light.

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Standard (Proteinogenic) Amino Acids

The set of 20 amino acids found in proteins, plus selenocysteine and pyrrolysine that are incorporated ribosomically into proteins.

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Non-Standard Amino Acids

Amino acids that are not found in proteins. They may have other functions in the body.

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Hydroxyl-containing Amino Acids

Amino acids with side chains containing hydroxyl groups (-OH), such as serine, threonine, and tyrosine.

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Sulfur-containing Amino Acids

Amino acids with side chains containing a sulfhydryl group (-SH), like cysteine.

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Positively Charged Amino Acids

Amino acids with side chains that are positively charged at neutral pH, such as lysine, arginine, and histidine.

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Negatively Charged Amino Acids

Amino acids with side chains that are negatively charged at neutral pH, such as aspartate and glutamate.

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Aliphatic Amino Acids

Amino acids with aliphatic side chains, which are non-polar and hydrophobic, such as glycine, alanine, valine, and leucine.

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Aromatic Amino Acids

Amino acids with aromatic side chains containing a ring structure, such as phenylalanine, tyrosine, and tryptophan.

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Carboxylic-containing Amino Acids

Amino acids with side chains containing carboxyl groups (-COOH), such as aspartate and glutamate.

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Amide-containing Amino Acids

Amino acids with side chains containing amide groups (-CONH2), such as asparagine and glutamine.

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Study Notes

Amino Acids and Proteins

  • Amino acids are organic compounds that contain carbon, hydrogen, oxygen, and nitrogen.
  • They are monomers that form proteins.
  • A-amino acids have an amino group (-NH2) and a carboxyl group (-COOH) attached to the same alpha carbon (α-carbon).
  • The side chain (R group) varies between different amino acids, making them unique.
  • Proline is a secondary amino acid, with a secondary amino group (-NH-).
  • Many naturally occurring amino acids aren't found in proteins; these structures differ from α-amino acids.

Amino Acid Structure

  • The R group attached to the α-carbon distinguishes each amino acid.
  • Glycine has a hydrogen atom as its R group.
  • Lysine has a longer side chain.
  • Proline's secondary amino group makes it unique.

Amino Acids as Acids and Bases

  • Amino acids contain both amino (-NH2) and carboxyl (-COOH) groups.
  • At physiological pH (~7.2), amino groups are protonated (-NH₃⁺) and carboxyl groups are deprotonated (-COO⁻).
  • This creates a zwitterion form (a dipolar ion) in solution, with a positive and a negative charge balancing each other.
  • The ionization of amino acids changes with pH.

Isomers

  • Isomers are compounds with the same molecular formula but different structures.
  • Constitutional isomers have different atomic connectivities.
  • Stereoisomers have the same atomic connectivity but differ in spatial arrangement.
  • Enantiomers are non-superimposable mirror images, while diastereomers are not mirror images.
  • Chiral molecules have no plane of symmetry, and exist as enantiomers.

Absolute Configuration

  • All amino acids except glycine are chiral.
  • Chiral amino acids exist as two non-superimposable mirror images called enantiomers and have different configurations denoted as D or L based on glyceraldehyde's configuration.
  • The absolute configuration is identified by the absolute configuration of the a-carbon determining the L or D isomer.

Optical Activity

  • Chiral molecules (except glycine) can rotate plane-polarized light.
  • Dextrorotatory (+): rotations clockwise
  • Levorotatory (-): rotations counterclockwise
  • Specific rotation, a measure of a sample's optical activity, uses a polarimeter.

Titration of Amino Acids

  • Amino acids are titrated using a strong base (like NaOH) to determine the effect of pH on net charge.
  • Different amino acids, with and without ionizable side chains, can be titrated to understand their pKa values for better prediction.

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