Molecular and crystal structure of an amphiphile: 4'-propoxybiphenyl-4-methyl-N,N-dimethylamineoxide dihydrate

Biochim Biophys Acta. 1995 Mar 22;1234(2):244-8. doi: 10.1016/0005-2736(94)00294-y.

Abstract

A novel amphiphile, 4'-propoxybiphenyl-4-methyl-N,N-dimethylamineoxide, has been synthesized, crystallized (P2(1)/a, a = 9.084 A, b = 8.911 A, c = 22.460 A, beta = 96.224 degrees) and its crystal structure was determined. The amphiphile forms a bilayer in which the amineoxide oxygen of each molecule binds two water molecules. In the hydrophobic part of the bilayer the biphenyls form edge-to-face contacts, in the polar layer there is a hydrogen bonding network. The potential use of the compound as a detergent for membrane proteins has been demonstrated and the relevance of the amineoxide hydrate for other detergents discussed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biphenyl Compounds / chemical synthesis
  • Biphenyl Compounds / chemistry*
  • Biphenyl Compounds / pharmacology
  • Crystallography, X-Ray
  • Detergents
  • Hydrogen Bonding
  • Lipid Bilayers*
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Photosynthetic Reaction Center Complex Proteins / isolation & purification
  • Rhodopseudomonas / metabolism

Substances

  • Biphenyl Compounds
  • Detergents
  • Lipid Bilayers
  • Photosynthetic Reaction Center Complex Proteins
  • 4'-propoxybiphenyl-4-methyl-N,N-dimethylamineoxide