Further study of the chemical structure of the equine erythrocyte hematoside containing O-acetyl ester.
Abstract: The chemical structure of an equine hematoside, which contained an ester group and comprised 72% of the total erythrocyte gangliosides, was determined by means of nondestructive and destructive procedures. A 400-MHz nuclear magnetic resonance spectrum of the ganglioside in perdeuterodimethyl sulfoxide demonstrated three protons due to a methyl group of an acetyl moiety, as well as amide and anomeric protons which were compatible with those of the ordinary hematoside. The spin decoupling difference spectroscopy of the ganglioside revealed the presence of the following structures. [formula: see text]. A mass spectrum obtained by direct probe analysis of the permethylated ganglioside demonstrated the presence of an O-acetyl-N-glycolylneuraminic acid moiety (m/z 434). Gas chromatography-mass spectrometric analysis of the sialic acid, derivatives from the periodate-oxidized ganglioside, and derivatives from acetalized ganglioside prepared under controlled conditions indicated that the sialic acid of the ganglioside was 4-O-acetyl-N-glycolylneuraminic acid. Thus, the structure of the equine ganglioside was determined as 4-O-acetyl-N-glycolylneuraminyl alpha 2-3 galactosyl beta 1-4 glucosyl beta 1-ceramide. The antigenic properties of this ganglioside were examined. In contrast to ordinary hematoside, which reacted strongly with Hanganutziu-Deicher (H-D) antibodies of a heterophile type in human, this ganglioside did not exhibit any H-D antigenicity. Therefore, a free hydroxy group at C-4 of the N-glycolylneuraminyl moiety in gangliosides appears to be absolutely required for the manifestation of H-D antigenicity.
Publication Date: 1983-01-25 PubMed ID: 6822513
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- Journal Article
- Research Support
- Non-U.S. Gov't
Summary
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The research article outlines the study of specific properties and structures of an equine hematoside, focusing on its reaction with specific antibodies. The structure was determined through non-destructive and destructive methods and found to have specific conditions for exhibiting antigenicity.
Structure Determination of Equine Hematoside
- The researchers analyzed the chemical structure of an equine hematoside, a substance which forms a large portion of the total erythrocyte gangliosides.
- To scrutinize the structure, they used nondestructive and destructive procedures, while a 400-MHz nuclear magnetic resonance spectrum held the key to understanding the substance’s chemical properties.
- The nuclear magnetic resonance spectrum showed three protons from a methyl group of an acetyl moiety, amide, and anomeric protons that are compatible with an ordinary hematoside.
Additional Structural Discoveries
- Through spin decoupling difference spectroscopy, the study revealed more comprehensive structure of the ganglioside.
- A mass spectrum obtained during the analysis showed the presence of an O-acetyl-N-glycolylneuraminic acid moiety.
- Finally, using gas chromatography-mass spectrometric analysis, it was indicated that the sialic acid of the ganglioside was 4-O-acetyl-N-glycolylneuraminic acid, allowing the structure of the equine ganglioside to be established.
Insights Into Antigenic Properties
- The researchers examined the antigenic properties of the newly discovered ganglioside.
- Unlike an ordinary hematoside that strongly reacts with Hanganutziu-Deicher (H-D) antibodies (typically found in humans), the studied ganglioside did not exhibit any H-D antigenicity.
- This suggests the necessity of a free hydroxy group at C-4 of the N-glycolylneuraminyl moiety in the gangliosides for displaying H-D antigenicity, indicating specific conditions under which the particular hematoside can exhibit antigenic properties.
Cite This Article
APA
Gasa S, Makita A, Kinoshita Y.
(1983).
Further study of the chemical structure of the equine erythrocyte hematoside containing O-acetyl ester.
J Biol Chem, 258(2), 876-881.
Publication
Researcher Affiliations
MeSH Terms
- Animals
- Chemical Phenomena
- Chemistry
- Erythrocytes / analysis
- G(M3) Ganglioside / blood
- Gangliosides / blood
- Horses
- Magnetic Resonance Spectroscopy
- Mass Spectrometry
Citations
This article has been cited 12 times.- Guo Z. The Structural Diversity of Natural Glycosphingolipids (GSLs).. J Carbohydr Chem 2022;41(2-3):63-154.
- Schauer R, Kamerling JP. Exploration of the Sialic Acid World.. Adv Carbohydr Chem Biochem 2018;75:1-213.
- Wasik BR, Barnard KN, Ossiboff RJ, Khedri Z, Feng KH, Yu H, Chen X, Perez DR, Varki A, Parrish CR. Distribution of O-Acetylated Sialic Acids among Target Host Tissues for Influenza Virus.. mSphere 2017 Sep-Oct;2(5).
- Minami A, Ishibashi S, Ikeda K, Ishitsubo E, Hori T, Tokiwa H, Taguchi R, Ieno D, Otsubo T, Matsuda Y, Sai S, Inada M, Suzuki T. Catalytic preference of Salmonella typhimurium LT2 sialidase for N-acetylneuraminic acid residues over N-glycolylneuraminic acid residues.. FEBS Open Bio 2013;3:231-6.
- Romero-Ramírez L, García-Álvarez I, Campos-Olivas R, Gilbert M, Goneau MF, Fernández-Mayoralas A, Nieto-Sampedro M. Specific synthesis of neurostatin and gangliosides O-acetylated in the outer sialic acids using a sialate transferase.. PLoS One 2012;7(12):e49983.
- Niimura Y, Ishizuka I. Unique disialosyl gangliosides from salmon kidney: characterization of V3alphaFuc, IV3betaGalNAc, II3(alphaNeuAc)2-Gg4Cer and its analogue with 4-O-acetyl-N-acetylneuraminic acid.. Glycoconj J 2006 Nov;23(7-8):489-99.
- Daino T, Tsuchihashi K, Kashiwagi M, Yachida Y, Akino T, Gasa S. Antigenicity of the carbohydrate moiety of ganglioside GM3 having 3-O-acetyl ceramide.. Glycoconj J 1999 Jan;16(1):39-43.
- Kobasa D, Kodihalli S, Luo M, Castrucci MR, Donatelli I, Suzuki Y, Suzuki T, Kawaoka Y. Amino acid residues contributing to the substrate specificity of the influenza A virus neuraminidase.. J Virol 1999 Aug;73(8):6743-51.
- Yachida Y, Tsuchihashi K, Gasa S. Characterization of novel mono-O-acetylated GM3s containing 9-O-acetyl sialic acid and 6-O-acetyl galactose in equine erythrocytes.. Glycoconj J 1996 Apr;13(2):225-23.
- Xu G, Suzuki T, Maejima Y, Mizoguchi T, Tsuchiya M, Kiso M, Hasegawa A, Suzuki Y. Sialidase of swine influenza A viruses: variation of the recognition specificities for sialyl linkages and for the molecular species of sialic acid with the year of isolation.. Glycoconj J 1995 Apr;12(2):156-61.
- Smit H, Gaastra W, Kamerling JP, Vliegenthart JF, de Graaf FK. Isolation and structural characterization of the equine erythrocyte receptor for enterotoxigenic Escherichia coli K99 fimbrial adhesin.. Infect Immun 1984 Nov;46(2):578-84.
- Ono E, Abe K, Nakazawa M, Naiki M. Ganglioside epitope recognized by K99 fimbriae from enterotoxigenic Escherichia coli.. Infect Immun 1989 Mar;57(3):907-11.
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