title: Spin-labelled sulfur containing neoglycolipids.
abstract: A neoglycolipid of structure beta-D-Glcp-S-(CH2)3N(OH)(CH2)4-O-cholest-5-en-3 beta-yl has been prepared in fair overall yield by reduction of the nitrone obtained by condensation of beta-D-Glcp-S-(CH2)3NHOH and OCH-(CH2)3-O-cholest-5-en-3 beta-yl. This synthetic procedure is very flexible, allowing a large range of lengths for the spacer arm, different positions for the NOH group along the spacer arm chain and the replacement of the sulfur by other bio-isosteric groups. The new neoglycolipid spontaneously oxidized to the corresponding nitroxide free radical whose EPR spectrum gave information on its conformational equilibrium which was further studied by molecular mechanics.
authors.affiliation: Department of Pharmaceutical Chemistry, University of Geneva, Switzerland.
authors.forename: J M
authors.initials: JM
authors.lastname: Tronchet
authors.forename: M
authors.initials: M
authors.lastname: Zsély
authors.forename: A
authors.initials: A
authors.lastname: Ricca
authors.forename: F
authors.initials: F
authors.lastname: Barbalat-Rey
authors.forename: M
authors.initials: M
authors.lastname: Geoffroy
mesh_terms: D006017:Glycolipids / Q000138:chemical synthesis*; D013057:Spectrum Analysis; D013113:Spin Labels; D013455:Sulfur / Q000032:analysis*
chemical_list: D006017:Glycolipids; D013113:Spin Labels; D013455:Sulfur