A naturally occurring deaminated neuraminic acid, 3-deoxy-D-glycero-D-galacto-nonulosonic acid (KDN). Its unique occurrence at the nonreducing ends of oligosialyl chains in polysialoglycoprotein of rainbow trout eggs - PubMed (original) (raw)
. 1986 Sep 5;261(25):11550-7.
- PMID: 3745155
Free article
A naturally occurring deaminated neuraminic acid, 3-deoxy-D-glycero-D-galacto-nonulosonic acid (KDN). Its unique occurrence at the nonreducing ends of oligosialyl chains in polysialoglycoprotein of rainbow trout eggs
D Nadano et al. J Biol Chem. 1986.
Free article
Abstract
An unknown deaminated sialic acid has been isolated from Salmo gairdneri (rainbow trout) egg polysialoglycoprotein. A combination of structural methods including gas-liquid chromatography, chemical and enzymatic analyses, mass spectrometry, and 400-MHz 1H NMR spectroscopy was used to determine the structure as 2-keto-3-deoxy-D-glycero-D-galacto-nononic acid (= 3-deoxy-D-glycero-D-galacto-nonulosonic acid; KDN). This structure has been confirmed by comparison with a chemically synthesized authentic sample of KDN. The natural occurrence of deaminated sialic acid in biological material has not been previously reported. A series of KDN-containing oligosialic acids were isolated from the polysialoglycoprotein after pH 4.7-catalyzed hydrolysis. Structural studies including methylation analysis, mass spectrometry, 1H NMR spectroscopy, and chemical reactivity were also used to confirm the structures of the sialyloligosaccharides as KDN alpha 2[8NeuGc alpha 2-]n (n = 1-7). The exclusive location of KDN at the nonreducing termini in polysialoglycoproteins protects oligo(poly)sialyl chains from exosialidases. Terminal capping of these chains may be important in egg activation in salmonid fishes.
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