Lack of water transport by amino acid side chains or peptides entering a nonpolar environment

Biochemistry. 1993 Jul 13;32(27):6807-9. doi: 10.1021/bi00078a001.

Abstract

Water has been reported to enter cyclohexane in association with 3-methylindole, a model compound representing the side chain of tryptophan. Entrainment of water would cloud the interpretation of measured partition coefficients as a simple index of hydrophobicity. NMR and isotope-exchange experiments indicate that the reported entrainment of water resulted from unrecognized exchange of 3H from water into the -NH- group of the indole ring. A more detailed analysis shows that no significant amounts of excess water (less than 0.1 molecule/molecule of solute) enter cyclohexane with molecules representing the side chains of tryptophan, phenylalanine, threonine, lysine, or the peptide bond itself.

MeSH terms

  • Amino Acids / chemistry*
  • Cyclohexanes / chemistry*
  • Isotopes
  • Magnetic Resonance Spectroscopy
  • Peptides / chemistry*
  • Tritium
  • Water / chemistry*

Substances

  • Amino Acids
  • Cyclohexanes
  • Isotopes
  • Peptides
  • Water
  • Tritium