Spin-labelled sulfur containing neoglycolipids.
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.
Tronchet
J M
JM
Department of Pharmaceutical Chemistry, University of Geneva, Switzerland.
Zsély
M
M
Ricca
A
A
Barbalat-Rey
F
F
Geoffroy
M
M
D006017:Glycolipids / Q000138:chemical synthesis*; D013057:Spectrum Analysis; D013113:Spin Labels; D013455:Sulfur / Q000032:analysis*
D006017:Glycolipids; D013113:Spin Labels; D013455:Sulfur