Reaction #468397

ord-b7d5028972c64e99a632f9e0fdfef664

Reaction equation

CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO[C@@H]1O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O[C@@H]3O[C@H](CO)[C@H](O)[C@H](O[C@@H]4O[C@H](CO)[C@H](O)[C@H](O)[C@H]4O)[C@H]3NC(C)=O)[C@H](O[C@]3(C(=O)O)C[C@H](O)[C@@H](NC(C)=O)[C@H]([C@H](O)[C@H](O)CO)O3)[C@H]2O)[C@H](O)[C@H]1O)NC(=O)CCCCCCCCCCCCCCCCC
Ganglioside GM1
O
water
→
CCCCCCCCCCCCCCC#CC#CCCCC(=O)O
5,7-docosadiynoic acid

Reactants

CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO[C@@H]1O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O[C@@H]3O[C@H](CO)[C@H](O)[C@H](O[C@@H]4O[C@H](CO)[C@H](O)[C@H](O)[C@H]4O)[C@H]3NC(C)=O)[C@H](O[C@]3(C(=O)O)C[C@H](O)[C@@H](NC(C)=O)[C@H]([C@H](O)[C@H](O)CO)O3)[C@H]2O)[C@H](O)[C@H]1O)NC(=O)CCCCCCCCCCCCCCCCC
Ganglioside GM1
O
water

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.DISTILLATIONby passing distilled water through a Millipore μF ultrapurification train
  2. 2
    workup.ADDITIONThe ganglioside GM1 was mixed at 5 mol % with the diacetylene “matrix
  3. 3
    OtherLiposomes were prepared
  4. 4
    Otherthe probe sonication method
  5. 5
    Otherpolymerized by UV irradiation (254 nm)

Procedure

Ganglioside GM1, cholera toxin from Vibrio Cholerae, human serum albumin, and wheat germ agglutinin were purchased from Sigma. 5,7-docosadiynoic acid was synthesized. Deionized water was obtained by passing distilled water through a Millipore μF ultrapurification train. Solvents used were reagent grade. The ganglioside GM1 was mixed at 5 mol % with the diacetylene “matrix lipid” monomers. Liposomes were prepared using the probe sonication method and polymerized by UV irradiation (254 nm). The conjugated ene-yne backbone of polydiacetylene liposomes results in the appearance of a deep blue/purple solution. The visible absorption spectrum of the freshly prepared purple liposomes is shown in FIG. 25.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06306598B1uspto-grants-2001_10