Biochemistry

Amino Acid Structure

Building blocks of proteins — 20 standard amino acids with diverse side chains

Amino acids are organic molecules with both an amino group (-NH₂) and carboxylic acid group (-COOH) on the same carbon. The α-carbon also has an H and an R group (side chain) — defines the specific amino acid. 20 standard amino acids in proteins. R groups vary: hydrophobic (alanine, valine), polar uncharged (serine, threonine), positively charged (lysine, arginine), negatively charged (aspartate, glutamate), aromatic (phenylalanine, tryptophan), unique (cysteine, proline). At physiological pH: zwitterion form (NH₃⁺, COO⁻). Linked by peptide bonds → proteins.

  • Number standard20 amino acids in proteins
  • General structureH₂N-CHR-COOH (R = side chain)
  • At pH 7Zwitterion (NH₃⁺, COO⁻)
  • Categories (R group)Hydrophobic, polar, charged, aromatic, unique
  • Linked byPeptide bond (-NH-CO-)
  • ChiralityAll natural amino acids are L (S configuration except Cys)

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Why amino acids matter

  • Proteins. All proteins from amino acids.
  • Enzymes. Catalytic activity from specific residues.
  • Drug design. Many drugs target proteins.
  • Nutrition. Essential amino acids must come from diet.
  • Chirality. All natural L; pharmacological implications.
  • Structural biology. Side chain interactions fold proteins.
  • Cell biology. Signaling, transport, defense.

Common misconceptions

  • 20 amino acids in all life. Mostly; some 21st-22nd in specific organisms.
  • D-amino acids don't exist. They do; just not in proteins.
  • Amino acid has 1 charged form. Zwitterion at physiological pH.
  • All amino acids essential. 9 are essential; 11 can be synthesized.
  • Side chain doesn't matter. Defines protein function.
  • Peptide bonds easily rotate. Resonance restricts; partial double bond.

Frequently asked questions

What's an amino acid?

Molecule with both amino (-NH₂) and carboxylic acid (-COOH) groups on same carbon (α-carbon). Plus H and R (side chain). Generic structure: H₂N-CHR-COOH. R = different group for each amino acid. 20 standard ones in proteins. Each has 3-letter (Gly, Ala, Val, etc.) and 1-letter (G, A, V) codes.

What's a zwitterion?

Both + and - charges on same molecule (no net charge). At physiological pH, amino acids: NH₃⁺ (protonated amine) and COO⁻ (deprotonated acid). Zwitterion form. -NH₂ pKa ≈ 9-10; -COOH pKa ≈ 2. At pH 7: amine protonated; acid deprotonated. Net neutral.

What's the isoelectric point (pI)?

pH at which amino acid has zero net charge. For neutral side chains: pI = (pKa1 + pKa2)/2 ≈ 5-6. For acidic side chains (Asp, Glu): pI lower (~3). For basic side chains (Lys, Arg): pI higher (~10). pI useful for: separating amino acids by isoelectric focusing, determining behavior at given pH.

What's a peptide bond?

Amide bond between amino group of one amino acid and carboxylic acid of another. -NH-CO-. Forms by dehydration: -COOH + H₂N- → -CO-NH- + H₂O. Polypeptide: chain of many amino acids. Protein: large polypeptide with specific sequence + 3D structure. Peptide bond shows resonance — planar, restricts rotation; affects protein structure.

How are side chains classified?

By chemistry. (1) Nonpolar, hydrophobic: Ala, Val, Leu, Ile, Pro, Met, Phe, Trp, Cys (S-H acidic but generally hydrophobic). (2) Polar uncharged: Ser, Thr, Tyr, Asn, Gln. (3) Positively charged (basic): Lys, Arg, His. (4) Negatively charged (acidic): Asp, Glu. Categories influence: protein folding, solubility, function.

Why are all natural amino acids L?

Mystery of biological homochirality. All proteins use L-amino acids (S configuration, except Cys which is R). D-amino acids exist in nature (cell walls of bacteria, antibiotics) but not in proteins. Proposed origins: random + amplification, photosynthetic selection, meteorite-delivered. Origin of homochirality remains unsolved.

What's the genetic code connection?

DNA encodes proteins via codons (3 nucleotides = 1 amino acid). 64 codons; 20 amino acids + stop signals. Some amino acids have multiple codons (redundancy). Universal across nearly all life — strong evolutionary conservation. Translation: ribosome reads mRNA, attaches amino acids to chain via peptide bonds. Total: 20 standard amino acids in all living organisms.