Determination of the absolute configuration of sialic acids in gangliosides from the sea cucumber Cucumaria echinata.
Enantiomeric pairs of sialic acid, D- and L-NeuAc (N-acetylneuraminic acid), were converted to D- and L-arabinose, respectively, by chemical degradation. Using this method, the absolute configuration of the sialic acid residues, NeuAc and NeuGc (N-glycolylneuraminic acid), in the gangliosides from the sea cucumber Cucumaria echinata was determined to be the D-form. Although naturally occurring sialic acids have been believed to be the D-form on the basis of biosynthetic evidence, this is the first report of the determination of the absolute configuration of the sialic acid residues in gangliosides using chemical methods.
Kisa
Fumiaki
F
Faculty of Pharmaceutical Sciences, Kyushu University, Maidashi, Fukuoka, Japan.
Yamada
Koji
K
Miyamoto
Tomofumi
T
Inagaki
Masanori
M
Higuchi
Ryuichi
R
D000818:Animals; D001089:Arabinose / Q000737:chemistry*; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D048016:Cucumaria / Q000737:chemistry*; D005732:Gangliosides / Q000737:chemistry*; D008969:Molecular Sequence Data; D012794:Sialic Acids / Q000737:chemistry*; D013237:Stereoisomerism
D005732:Gangliosides; D012794:Sialic Acids; D001089:Arabinose