Ingrid 't Hart

75 Chemical synthesis of sulfoglycolipid analog SM1a-core3 4 Chapter 4 Chemical synthesis of an O -glycan analog of sulfoglycolipid SM1a: SM1-core3 A poten�al glycan an�gen for cancer-specific monoclonal an�body HAE3 Abstract : Sulfoglycolipids (SGLs) are important cancer biomarkers, making them interes�ng synthe�c targets. A microarray study revealed SGL SM1a as an an�gen for an�-epiglycanin an�body (AE3 or HAE3). It was surprising that a glycolipid an�gen for an�body HAE3 was iden�fied, since HAE3 is known to bind mucin glycoproteins. O -glycan epitopes similar to SM1a have been found on mucin glycoproteins, having a core3 (GlcNAcβ1,3GalNAcα-Ser/Thr) glycan residue in common. Therefore, a hybrid structure of SM1a and the core3 disaccharide was proposed as a poten�al ligand for HAE3, here named as SM1-core3 (Galβ1,3GalNAcβ1,4Galβ1,3GlcNAcβ1,3GalNAcα). We report here the chemical synthesis of the protected SM1-core3 glycan having an α-linked aminopentyl group at the reducing end for immobiliza�on. A block synthe�c approach (2 + 3) was chosen and the respec�ve disaccharide donor and trisaccharide acceptor were synthesized from five monosaccharide building blocks. A�er deprotec�on and sulfa�on of SM1- core 3, this sulfoglycolipid analog will be studied for its HAE3 binding proper�es in a glycan microarray