Abstract
Conditions have been established for the rapid and efficient conjugation of reducing oligosaccharides (di- to deca-saccharides) to dipalmitoyl phosphatidylethanolamine. The resulting neoglycolipids derived from several naturally occurring oligosaccharides and a series of N-linked high-mannose-type oligosaccharides released by hydrazinolysis from RNAase B showed specific and potent reactivities, as appropriate, with monoclonal antibodies to blood group Lewis(b), blood group A or a stage-specific embryonic (SSEA-1) antigen, or the lectin concanavalin A.
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Selected References
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- COTE R. H., MORGAN W. T. Some nitrogen-containing disaccharides isolated from human blood-group A substance. Nature. 1956 Nov 24;178(4543):1171–1172. doi: 10.1038/1781171a0. [DOI] [PubMed] [Google Scholar]
- Clausen H., Levery S. B., Nudelman E., Tsuchiya S., Hakomori S. Repetitive A epitope (type 3 chain A) defined by blood group A1-specific monoclonal antibody TH-1: chemical basis of qualitative A1 and A2 distinction. Proc Natl Acad Sci U S A. 1985 Feb;82(4):1199–1203. doi: 10.1073/pnas.82.4.1199. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Gooi H. C., Feizi T., Kapadia A., Knowles B. B., Solter D., Evans M. J. Stage-specific embryonic antigen involves alpha 1 goes to 3 fucosylated type 2 blood group chains. Nature. 1981 Jul 9;292(5819):156–158. doi: 10.1038/292156a0. [DOI] [PubMed] [Google Scholar]
- Gooi H. C., Hounsell E. F., Picard J. K., Lowe A. D., Voak D., Lennox E. S., Feizi T. Differing reactions of monoclonal anti-A antibodies with oligosaccharides related to blood group A. J Biol Chem. 1985 Oct 25;260(24):13218–13224. [PubMed] [Google Scholar]
- Hilkens J., Buijs F., Hilgers J., Hageman P., Calafat J., Sonnenberg A., van der Valk M. Monoclonal antibodies against human milk-fat globule membranes detecting differentiation antigens of the mammary gland and its tumors. Int J Cancer. 1984 Aug 15;34(2):197–206. doi: 10.1002/ijc.2910340210. [DOI] [PubMed] [Google Scholar]
- Hirohashi S., Clausen H., Yamada T., Shimosato Y., Hakomori S. Blood group A cross-reacting epitope defined by monoclonal antibodies NCC-LU-35 and -81 expressed in cancer of blood group O or B individuals: its identification as Tn antigen. Proc Natl Acad Sci U S A. 1985 Oct;82(20):7039–7043. doi: 10.1073/pnas.82.20.7039. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Liang C. J., Yamashita K., Kobata A. Structural study of the carbohydrate moiety of bovine pancreatic ribonuclease B. J Biochem. 1980 Jul;88(1):51–58. [PubMed] [Google Scholar]
- Magnani J. L., Spitalnik S. L., Ginsburg V. Antibodies against cell surface carbohydrates: determination of antigen structure. Methods Enzymol. 1987;138:195–207. doi: 10.1016/0076-6879(87)38016-4. [DOI] [PubMed] [Google Scholar]
- Ogata S., Muramatsu T., Kobata A. Fractionation of glycopeptides by affinity column chromatography on concanavalin A-sepharose. J Biochem. 1975 Oct;78(4):687–696. doi: 10.1093/oxfordjournals.jbchem.a130956. [DOI] [PubMed] [Google Scholar]
- Solter D., Knowles B. B. Monoclonal antibody defining a stage-specific mouse embryonic antigen (SSEA-1). Proc Natl Acad Sci U S A. 1978 Nov;75(11):5565–5569. doi: 10.1073/pnas.75.11.5565. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Strecker G., Trentesaux-Chauvet C., Riazi-Farzad T., Fournet B., Bouquelet S., Montreuil J. Mise en évidence d'une oligosaccharidosurie associée à diverses mélituries et détermination de la structure des oligosaccharides excrétés. Hypothèse concernant l'origine des oligosaccharides des liquides biologiques. C R Acad Sci Hebd Seances Acad Sci D. 1973 Oct 15;277(15):1569–1572. [PubMed] [Google Scholar]
- Takasaki S., Mizuochi T., Kobata A. Hydrazinolysis of asparagine-linked sugar chains to produce free oligosaccharides. Methods Enzymol. 1982;83:263–268. doi: 10.1016/0076-6879(82)83019-x. [DOI] [PubMed] [Google Scholar]
- Tang P. W., Gool H. C., Hardy M., Lee Y. C., Feizi T. Novel approach to the study of the antigenicities and receptor functions of carbohydrate chains of glycoproteins. Biochem Biophys Res Commun. 1985 Oct 30;132(2):474–480. doi: 10.1016/0006-291x(85)91158-1. [DOI] [PubMed] [Google Scholar]
- Wiegandt H., Ziegler W. The use of reductaminated sugars for the preparation of oligosaccharide conjugates, I. Synthetic glycolipids containing glycosphingolipid-derived oligosaccharides. Hoppe Seylers Z Physiol Chem. 1974 Jan;355(1):11–18. doi: 10.1515/bchm2.1974.355.1.11. [DOI] [PubMed] [Google Scholar]
- Wood C., Kabat E. A. Immunochemical studies of conjugates of isomaltosyl oligosaccharides to lipid. I. Antigenicity of the glycolipids and the production of specific antibodies in rabbits. J Exp Med. 1981 Aug 1;154(2):432–449. doi: 10.1084/jem.154.2.432. [DOI] [PMC free article] [PubMed] [Google Scholar]