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Amino Acids: Properties, pKa Values, and Structure

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Amino Acids

General Properties of Amino Acids

Amino acids are the building blocks of proteins and play a central role in biochemistry. Each amino acid contains an amino group, a carboxyl group, a hydrogen atom, and a distinctive side chain (R group) attached to a central carbon atom (α-carbon).

  • Structure: The general formula for an amino acid is NH2-CHR-COOH.

  • Classification: Amino acids are classified based on the properties of their side chains (e.g., nonpolar, polar, acidic, basic).

  • Chirality: Most amino acids (except glycine) are chiral and exist as L- and D- isomers; proteins are composed of L-amino acids.

pKa Values of Amino Acids

The pKa values of amino acids are important for understanding their ionization states at different pH levels, which affects protein structure and function.

  • Carboxyl Group pKa: Typically around 2.0

  • Amino Group pKa: Typically around 9.0

  • Side Chain pKa: Varies depending on the amino acid (e.g., acidic and basic side chains)

Example Table: pKa Values of Selected Amino Acids

Amino Acid

pKa (α-COOH)

pKa (α-NH3+)

pKa (Side Chain)

Glycine

2.34

9.60

-

Glutamic Acid

2.19

9.67

4.25

Lysine

2.18

8.95

10.53

Histidine

1.82

9.17

6.00

Arginine

2.17

9.04

12.48

Additional info: Table values inferred from standard biochemistry references.

Structure of Amino Acids

The chemical structure of amino acids can be represented as follows:

  • General Structure:

  • Example (Phenylalanine):

Example: The image contains a chemical structure, which appears to be a representation of an amino acid (possibly phenylalanine or a similar aromatic amino acid).

Isoelectric Point (pI) Calculation

The isoelectric point (pI) is the pH at which an amino acid has no net charge. It is calculated as the average of the pKa values of the ionizable groups.

  • For amino acids without ionizable side chains:

  • For amino acids with ionizable side chains:

Example: For glycine,

Summary Table: Amino Acid Properties

Amino Acid

Type

pI

Glycine

Nonpolar

5.97

Glutamic Acid

Acidic

3.22

Lysine

Basic

9.74

Histidine

Basic

7.59

Additional info: Table values inferred from standard biochemistry references.

Applications

  • Protein Structure: Amino acid properties determine protein folding and function.

  • Buffering Capacity: Amino acids act as buffers in biological systems due to their ionizable groups.

  • Clinical Relevance: Abnormal amino acid metabolism can lead to diseases such as phenylketonuria.

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