Sugar/steroid/sugar conjugates: sensitivity of lipid binding to sugar structure

Org Lett. 2003 Oct 30;5(22):4041-4. doi: 10.1021/ol030084r.

Abstract

[structure: see text]. Three steroids, each bearing a sugar on rings A and D, have been synthesized. Their effect on the "melting" behavior of a lipid bilayer depends on whether the sugar is glucose, galactose, or mannose. Packing constraints dictate how the lipid bilayer responds to the sugars.

Publication types

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

MeSH terms

  • 1,2-Dipalmitoylphosphatidylcholine / chemistry
  • Androstane-3,17-diol / analogs & derivatives*
  • Androstane-3,17-diol / chemistry
  • Calorimetry, Differential Scanning
  • Galactose / analogs & derivatives
  • Galactose / chemistry
  • Glucose / analogs & derivatives
  • Glucose / chemistry
  • Hexoses / chemistry*
  • Lipid Bilayers / chemistry
  • Liposomes / chemistry
  • Mannose / analogs & derivatives
  • Mannose / chemistry
  • Models, Chemical
  • Molecular Structure
  • Phase Transition
  • Steroids / chemistry

Substances

  • Hexoses
  • Lipid Bilayers
  • Liposomes
  • Steroids
  • Androstane-3,17-diol
  • 1,2-Dipalmitoylphosphatidylcholine
  • Glucose
  • Mannose
  • Galactose