Thermal and photochemical degradation of sodium N-acetylneuraminate

Article abstract of DOI:10.1016/0008-6215(91)84042-D

The thermal and photochemical degradation products of sodium N-acetylneuraminate (sodium Neu5Ac) were investigated by means of ¹H- and ¹³C-n.m.r. spectroscopy, and mass spectrometry.Under all thermal conditions, sodium 5-acetamido-4,8-anhydro-3,5-dideoxy-D-glycero-D-galacto-nonulosonate (sodium N-acetyl-4,8-anhydroneuraminate) was obtained as the main product; on heating in alkaline solution, 4-acetamido-3,7-anhydro-2,4-dideoxy-D-glycero-D-galacto-octonic acid, pyrrole-2-carboxylic acid, and sodium 5-(D-arabino-tetrahydroxybutyl)pyrrole-2-carboxylate; on heating in acidic solution, sodium 5-(D-erythro-furanosyl)pyrrole-2-carboxylate and sodium 5-acetamido-2,7-anhydro-3,5-dideoxy-D-glycero-α-D-galacto-nonulopyranosonate (sodium N-acetyl-2,7-anhydroneuraminate); on refluxing in neutral solution 2-(β-D-erythro-furanosyl)pyrrole; and on heating of sodium Neu5Ac powder, 5-acetamido-2,6-anhydro-3,5-dideoxy-D-glycero-D-galacto-non-2-enonic acid were obtrained.Furthermore, on exposure to u.v. light (360nm), 4-acetamido-2,4-dideoxy-D-glycero-D-galacto-octonic acid was produced.