Effect of carboxylic acid side chains on the absorption maximum of visual pigments

Science. 1989 Nov 17;246(4932):928-30. doi: 10.1126/science.2573154.


The proposal that the absorption maximum of the visual pigments is governed by interaction of the 11-cis-retinal chromophore with charged carboxylic acid side chains in the membrane-embedded regions of the proteins has been tested by mutating five Asp and Glu residues thought to be buried in rhodopsin. Changing Glu113 to Gln causes a dramatic shift in the absorption maximum from 500 nanometers to 380 nanometers, a decrease in the pKa (acidity constant) of the protonated Schiff base of the chromophore to about 6, and a greatly increased reactivity with hydroxylamine. Thus Glu113 appears to be the counterion to the protonated Schiff base. Wavelength modulation in visual pigments apparently is not governed by electrostatic interaction with carboxylate residues, other than the counterion.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Aspartic Acid*
  • Glutamates
  • Glutamic Acid
  • Hydrogen-Ion Concentration
  • Hydroxylamine
  • Hydroxylamines / pharmacology
  • Models, Molecular
  • Mutation
  • Protein Conformation
  • Retinal Pigments / metabolism*
  • Retinaldehyde / metabolism*
  • Retinoids / metabolism*
  • Rhodopsin / genetics
  • Rhodopsin / metabolism*
  • Schiff Bases
  • Spectrophotometry


  • Glutamates
  • Hydroxylamines
  • Retinal Pigments
  • Retinoids
  • Schiff Bases
  • Hydroxylamine
  • Aspartic Acid
  • Glutamic Acid
  • Rhodopsin
  • Retinaldehyde