Mnemonic

Amino Acid Classification

A memory aid for grouping amino acids by side chain.

Expansion

Nonpolar, polar, acidic and basic, determined by the R group

Expansion

  • Nonpolar (hydrophobic): glycine, alanine, valine, leucine, isoleucine, methionine, phenylalanine, tryptophan, proline. Cluster in the core of soluble proteins and in membrane-spanning regions
  • Polar uncharged: serine, threonine, cysteine, tyrosine, asparagine, glutamine. Serine, threonine and tyrosine are the targets of phosphorylation
  • Acidic (negatively charged): aspartate and glutamate
  • Basic (positively charged): lysine, arginine and histidine

Special residues worth knowing individually:

  • Glycine: smallest, so it provides flexibility and is obligatory at every third position in collagen
  • Proline: its ring introduces a kink and breaks alpha helices
  • Cysteine: forms disulphide bridges, stabilising tertiary structure
  • Histidine: its pKa near physiological pH makes it the key buffering residue in haemoglobin and a common catalytic residue

The distribution of charge determines the isoelectric point, which is exploited in electrophoresis, and explains why a single charge-changing substitution such as glutamate to valine in sickle cell disease alters solubility so dramatically.