A convenient route to conjugates of 1,2-diglycerides with functionalized oligoethylene glycol spacer arms

A controlled reaction of a mixture of structural isomers of diacylglycerol (DAG) with N,N-disuccinimidyl carbonate and then with b-alanine provided intermediates of 1,2-diacylglycerol (1,2-DAG) which were further modified with carboxy- and amino-terminated oligoethylene glycol spacer arms of different length. As an example of bioactive molecules intended for the incorporation in lipid bilayer of artificial or cell membranes, 1,2-DAGs bearing tetrasaccharide Sialyl Lewis X or triglycine at the terminus of polar spacer were synthesized. The synthetic scheme can be readily scaled-up by the use of DAGs from food industry.