Structure elucidation of blood group B-like and I-active ceramide eicosa- and pentacosa-saccharides from rabbit erythrocyte membranes by combined gas chromatography-mass spectrometry; electron-impact and fast-atom-bombardment mass spectrometry; and two-dimensional correlated, relayed-coherence transfer, and nuclear overhauser effect 500-MHz 1H-N.m.r. spectroscopy

The structures of two glycosphingolipids, a ceramide eicosasaccharide BIrab-3 and a ceramide pentacosasaccharide BIrab-4 with "B-like" and distinct I blood-group activity, isolated in high yield from rabbit erythrocyte membranes, were investigated. The determination of their general structure, alpha-D-Galp-(1----3)-beta-D-Galp-(1----4)-beta-D-GlcpNAc-(1----3)- [alpha-D-Galp-(1----3)-beta-D-Galp-(1----4)-beta-D-Glcp-NAc-(1----6)]-be ta- D-Galp-(1----n4)-beta-D-GlcpNAc-(1----3)-beta-D-Galp-(1----4)-beta-D-Gl cp- (1----1)-ceramide, with n = 3 for BIrab-3 and n = 4 for BIrab-4, was based on the results of methylation analysis, fast-atom-bombardment and electron-impact mass spectrometry, 1D and 2D COSY, RCT, and n.O.e. 1H-N.m.r. spectra, and specific enzymic and chemical degradation

Fucose-containing oligosaccharides from human milk from a donor of blood group 0 Le(a) nonsecretor

The neutral oligosaccharides from the milk of a single donor with blood group 0, Lewis(a+b-) nonsecretor were separated into 18 fractions essentially according to the number of carbohydrate constituents using gel permeation chromatography on Biogel P-4 and Fractogel TSK HW-40. Further separation was achieved by HPLC and by HPTLC after reduction and peracetylation. The fractions obtained were analysed by FAB mass spectrometry with and without derivatization and by one- and two-dimensional proton NMR. Besides the already described 3-fucosidolactose, fucopentaose II (2), fucopentaose III (6) and difucohexaose II (4) the following fucosylated oligosaccharides could be identified. Among the higher oligosaccharides a branched lacto-N-decaose (12) was obtained in pure form after removal of the fucose residues by mild acid treatment

Structures of fucose‐containing ceramide pentasaccharides from the plasma of blood group O Le(a−b−) nonsecretors

A minor, Lec blood‐group inactive ceramide pentasaccharide double band fraction has been isolated from the plasma of blood group O Le(a−b−) nonsecretors. The two purified glycolipids were analysed by NMR spectroscopy, mass spectrometry and combined gas chromatography‐mass spectrometry. The following structures could be established: GlcNAc(β1 → 3)Gal(β1 → 4)Glc(β1 → 1)Cer (I); Gal(β1 → 4) [Fuc(α1 → 3)]GlcNAc(β1 → 3)Gal(β1 → 4)Glc(β1 → 1)Cer (II). It must be concluded that at least part of the secretor gene‐independent plasmatic H type 2 blood‐group activity can be attributed to glyco‐sphingolipid I, whereas substance II, originally detected in cancerous tissue, also occurs in the plasma of healthy individuals

DIFFERENT BINDING-CAPACITIES OF INFLUENZA-A AND SENDAI VIRUSES TO GANGLIOSIDES FROM HUMAN GRANULOCYTES

Müthing J, UNLAND F, HEITMANN D, et al. DIFFERENT BINDING-CAPACITIES OF INFLUENZA-A AND SENDAI VIRUSES TO GANGLIOSIDES FROM HUMAN GRANULOCYTES. GLYCOCONJUGATE JOURNAL. 1993;10(1):120-126.The structures of gangliosides from human granulocytes were elucidated by fast atom bombardment mass spectrometry and by gas chromatography/mass spectrometry as their partially methylated alditol acetates. In human granulocytes besides G(M3) (II3Neu5Ac-LacCer), neolacto-series gangliosides (IV3Neu5Ac-nLcOse4Cer, IV6Neu5Ac-nLcOse4Cer and VI3Neu5Ac-nLcOse6Cer) containing C24:1, and to some extent C22:0; and C-16:0 fatty acid in their respective ceramide portions, were identified as major components. In this study we demonstrate that gangliosides from human granulocytes, the second most abundant cells in peripheral blood, can serve as receptors for influenza viruses A/PR/8/34 (H1N1), A/X-31 (H3N2), and a parainfluenza virus Sendai virus (HNF1, Z-strain). Viruses were found to exhibit specific adhesion to terminal Neu5Acalpha2-3Gal and/or Neu5Acalpha2-6Gal sequences as well as depending on the chain length of ganglioside carbohydrate backbones from human granulocytes, these important effector cells which represent the first line of defence in immunologically mediated reactions