N-Acetylneuraminic Acid Analogues

Abstract

The 8-carbon and the 7-carbon analogues of N-acetyl-neuraminic acid were necessary in order to study some of the structural requirements of N-acetylneuraminic acid in its role as substrate for certain enzymes. The 8-carbon analogue of N-acetylneuraminic acid was synthesized by the alkaline condensation of 2-acetamido-2-deoxy-d-lyxose and di-tert-butyloxaloacetate. This same 8-carbon compound and the 7-carbon analogue of N-acetylneuraminic acid were isolated after acid hydrolysis of Collocalia mucoid which had been modified by periodate oxidation followed by borohydride reduction. The two analogues could also be detected when periodate oxidation and borohydride reduction were applied to crystalline β-methoxy-N-acetylneuraminic acid methyl ester.