SYNTHESIS OFN⁴-(2-ACETAMIDO-2-DEOXY-β-D-GLUCOPYRANOSYL)-L-ASPARAGINE ANALOGUES.L-2-CHLORO-,L-2-BROMO-, ANDD,L-2-METHYLSUCCINAMIC ACID ANALOGUES

L-Chlorosuccinic anhydride, L-bromosuccinic anhydride, and D,L-methylsuccinic anhydride react with 2-acetamido-2-deoxy-β-D-glucopyranosylamine to give varying mixtures of N 4-(β-GlcNAc)-2-substituted- and N 4-(β-GlcNAc)-3-substituted-succinamic acid isomers. The two regioisomers are separated by anion exchange chromatography. The N 4-(β-GlcNAc)-2-substituted-succinamic acid isomers are characterized as analogues of N 4-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-L-asparagine.