CHARACTERIZATION OF THE SULFATED FUCOSE-CONTAINING TRISACCHARIDES BY FAST-ATOM-BOMBARDMENT TANDEM MASS-SPECTROMETRY IN THE STUDY OF THE ACROSOME REACTION-INDUCING SUBSTANCE OF THE STARFISH, ASTERIAS-AMURENSIS

Fast atom bombardment mass spectrometry (FABMS) and collision-induced dissociation tandem mass spectrometry (CID-MS/MS) were applied in the investigation of the anomeric isomerism of synthetic trisaccharides co nsisting of xylose, galactose and sulfated fucose {Xyl1 --> 3Gal alpha 1 --> 3(4-OSO3Na)Fuc} and {Xyl1 --> 3Gal alpha 1 --> 4(3-OSO3Na)Fuc} and the linkage position of the sulfate group, It was possible to diff erentiate between various glycosidic linkages in several synthetic tri saccharides, The position of a sulfate group in synthetic methyl O-sul fo-alpha-L-fucopyranoside isomers was elucidated from the fragmentatio n patterns, Comparing the data from synthetic sulfated trisaccharides with the spectra from the natural compound derived from glycan chains of the acrosome reaction-inducing substance (ARIS) from starfish, the anomeric structure and the position of the sulfate group in the natura l sample were determined without ambiguity as Xyl beta 1 --> 3Gal alph a 1 --> 3(4-OSO3-)Fuc, in agreement with the result from an independen t study based on nuclear magnetic resonance, (C) 1998 by John Wiley & Sons, Ltd.