title: On the side-chain conformation of N-acetylneuraminic acid and its epimers at C-7, C-8, and C-7,8.
abstract: The side-chain conformation of N-acetylneuraminic acid and analogs has been studied by n.m.r. spectroscopy. The results of the 1H-, 13C-n.m.r.-, and 1H-nuclear-Overhauser-enhancement measurements were used to distinguish between different local-minima conformations suggested by hard-sphere calculations. Attempts were made to correlate the major conformation determined for each compound with the behavior towards activation with N-acetylneuraminic acid-CMP-synthetase.
mesh_terms: D002236:Carbohydrate Conformation; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008958:Models, Molecular; D019158:N-Acetylneuraminic Acid; D012794:Sialic Acids / Q000138:chemical synthesis; D013237:Stereoisomerism
chemical_list: D012794:Sialic Acids; D019158:N-Acetylneuraminic Acid