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An expeditious synthesis of blood-group antigens, ABO histo-blood group type II antigens and xenoantigen oligosaccharides with amino type spacer−arms

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Abstract

Blood group oligosaccharides are one of the most clinically important antigen families and they may also act as secondary ligands for bacterial toxins from Escherichia coli and Vibrio cholerae. Herein we report the synthesis of spacered (sp = CH2CH2CH2NH2) glycosides of A antigen {α-D-GalNAc-(l→3)-[α-L-Fuc-(l→2)]-β-D-Gal-}, B antigen{α-D-Gal-(l→3)-[α-L-Fuc-(l→2)]-β-D-Gal-}, LewisX{α-D-Gal-(l→4)-[α-L-Fuc-(l→3)]-β-D-GlcNAc-}, A type-II {α-D-GalNAc-(l→3)-[α-L-Fuc-(l→2)]-β-D-Gal-(1→4)-β-D-GlcNAc-}, B type-II {α-D-Gal-(l→3)-[α-L-Fuc-(l→2)]-β-D-Gal-(1→4)-β-D-GlcNAc-}, H type-II{α-L-Fuc-(l→2)-β-D-Gal-(1→4)-β-D-GlcNAc-}, xenoantigen {α-D-Gal-(l→3)-β-D-Gal-(1→4)-[α-L-Fuc-(l→2)]-β-D-GlcNAc-} and Linear B Type II {α-D-Gal-(l→3)-β-D-Gal-(1→4)-β-D-GlcNAc-} useful for a range of biochemical investigations. This linker was chosen so as to facilitate the future conjugation of the antigens to proteins or other molecules. We also measured the affinities of some synthesized oligosaccharides against El Tor CTB strain from V. cholera.

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References

  1. Watkins W.M., Morgan W.T.J.: Specific inhibition studies relating to the Lewis blood-group system. Nature. 180, 1038–1040 (1957)

    Article  CAS  PubMed  Google Scholar 

  2. Morgan W.T.J., Watkins W.M.: Genetic and biochemical aspects of human blood-group A-, B-, H-, Le-a- and Le-b-specificity. Br. Med. Bull. 25, 30–34 (1969)

    CAS  PubMed  Google Scholar 

  3. Kabat E.A.: Immunochemical studies on the carbohydrate moiety of water soluble blood group A, B, H, Lea and Leb substances and their precursor I antigens. In: Isbell H. (ed.) Carbohydrates in solution (Adv chemistry series 117), pp. 334–361. American Chemical Society, Washington, DC (1973)

    Chapter  Google Scholar 

  4. Yamamoto F.: ABO blood group system-ABH oligosaccharide antigens, anti-A and anti-B, A and B glycosyltransferases, and ABO genes. Immunohematology. 20, 3–22 (2004)

    CAS  PubMed  Google Scholar 

  5. West L.J., Pollock-Barziv S.M., Dipchand A.I., Lee K.J., Cardella C.J., Benson L.N., Rebeyka I.M., Coles J.G.: ABO-incompatible heart transplantation in infants. N. Engl. J. Med. 344, 793–800 (2001)

    Article  CAS  PubMed  Google Scholar 

  6. Breimer M.E.: Tissue specificity of glycosphingolipids as expressed in pancreas and small intestine of blood group A and B human individuals. Arch. Biochem. Biophys. 228, 71–85 (1984)

    Article  CAS  PubMed  Google Scholar 

  7. Björk S., Breimer M.E., Hansson G.C., Karlsson K.A., Leffler H.: Structures of blood group glycosphingolipids of human small intestine. A relation between the expression of fucolipids of epithelial cells and the ABO, Le and Se phenotype of the donor. J. Biol. Chem. 262, 6758–6765 (1987)

    PubMed  Google Scholar 

  8. Finne J., Breimer M.E., Hansson G.C., Karlsson K.A., Leffler H., Vliegenthart J.F., Halbeek H.V.: Novel polyfucosylated N-linked glycopeptides with blood group A, H, X, and Y determinants from human small intestinal epithelial cells. J. Biol. Chem. 264, 5720–5735 (1989)

    CAS  PubMed  Google Scholar 

  9. Gao S., Bennet E.P., Reibel J., Chen X., Christensen M.E., Krogdahl A., Dabelsteen E.: Histo-blood group ABO antigen in oral potentially malignant lesions and squamous cell carcinoma-genotypic and phenotypic characterization. Apmis. 112, 11–20 (2004)

    Article  PubMed  Google Scholar 

  10. Paré G., Chasman D.I., Kellog M., Zee R.Y.L., Rifai N., Badola S., Miletich J.P., Ridker P.M.: Novel association of ABO histo-blood group antigen with soluble ICAM-1: results of a genome-wide association study of 6, 578 women. PLoS Genet. 4, 1–8 (2008)

    Article  Google Scholar 

  11. Nosaka M., Ishida Y., Tanaka A., Hayashi T., Miyashita T., Kaminaka C., Eisenmenger W., Furukawa F., Kimura A.: Aberrant expression of histo-blood group a type 3 antigens in vascular endothelial cells in inflammatory sites. J. Histochem. Cytochem. 56, 223–231 (2008)

    Article  PubMed Central  CAS  PubMed  Google Scholar 

  12. Cooper D.K., Good A.H., Koren E., Oriol R., Malcolm A.J., Ippolito R.M., Neethling F.A., Ye Y., Romano E., Zuhdi N.: Identification of alpha-galactosyl and other carbohydrate epitopes that are bound by human anti-pig antibodies: relevance to discordant xenografting in man. Transpl. Immunol. 1, 198–205 (1993)

    Article  CAS  PubMed  Google Scholar 

  13. Mall A.S.: Analysis of mucins: role in laboratory diagnosis. J. Clin. Pathol. 61, 1018–1024 (2008)

    Article  CAS  PubMed  Google Scholar 

  14. Le Pendu J., Marionneau S., Cailleau-Thomas A., Rocher J., Le Moullac-Vaidye B., Clément M.: ABH and Lewis histo-blood group antigens in cance. APMIS. 109, 9–26 (2001)

    Article  PubMed  Google Scholar 

  15. Hellström I., Garrigues H.J., Garrigues U., Hellström K.E.: Highly tumor-reactive, internalizing, mouse monoclonal antibodies to Ley-related cell surface antigens. Cancer Res. 50, 2183–2190 (1990)

    PubMed  Google Scholar 

  16. Holmner A., Askarieh G., Ökvist M., Krengel U.: Blood group antigen recognition by Escherichia coli heat-labile enterotoxin. J. Mol. Biol. 371, 754–764 (2007)

    Article  CAS  PubMed  Google Scholar 

  17. Holmner A., Lebens M., Teneberg S., Angstrom J., Ökvist M., Krengel U.: Novel binding site identified in a hybrid between cholera toxin and heat-labile enterotoxin: 1.9 Å crystal structure reveals the details. Structures. 12, 1655–1667 (2004)

    Article  CAS  Google Scholar 

  18. Glass R.I., Holmgren J., Haley C.E., Khan M.R., Svennerholm A.M., Stoll B.J., Belayet Hossain K.M., Black R.E., Yunus M., Barua D.: Predispositionfor choleraofindividuals with O blood group possible evolutionary significance. Am. J. Epidemiol. 121, 791–796 (1985)

    CAS  PubMed  Google Scholar 

  19. Holmner A., Mackenzie A., Krengel U.: Molecular basis of cholera blood-group dependence and implications for a world characterized by climate change. FEBS Lett. 584, 2548–2555 (2010)

    Article  CAS  PubMed  Google Scholar 

  20. Meloncelli P.J., Lowary T.L.: Synthesis of ABO histo-blood group type I and II antigens. Carbohydr. Res. 345, 2305–2322 (2010)

    Article  CAS  PubMed  Google Scholar 

  21. Paulsen H., Kolař Č.: Bausteine von oligosacchariden, XX1) synthese der oligosaccharid-determinanten der blutgruppensubstanzen der type 2 des ABH-systems. Diskussion der α-Glycosid-Synthese. Chem. Ber. 114, 306–321 (1981)

    Article  CAS  Google Scholar 

  22. Bovin N.V., Zurabyan S.E., Khorlin A.Y.: Stereoselectivity in glycosylation by means of 2-azido-2-desoxy-D-galactopyranose derivatives and the synthesis of the determinative oligosaccharide of blood group A, type 1. Russ. Chem. Bull. 31, 1023–1030 (1982)

    Article  Google Scholar 

  23. Pazynina G.V., Tyrtysh T.V., Bovin N.V.: Synthesis of histo blood-group antigens A and B (type 2), xenoantigen Gal1-3Gal1-4GlNAc, and related type 2 backbone oligosaccharides as haptens in spacered form. Mendeleev Commun. 12, 143–145 (2002)

    Article  Google Scholar 

  24. Korchagina E.Y., Ryzhov I.M., Byrgazov K.A., Popova I.S., Pokrovsky S.N., Bovin N.V.: Block synthesis of blood group tetrasaccharides B (types 1, 3 and 4). Mendeleev Commun. 19, 152–154 (2009)

    Article  CAS  Google Scholar 

  25. Eklind K., Gustafsson R., Tiden A.K., Norberg T., Aberg P.M.: Large-scale synthesis of a Lewis b tetrasaccharide derivative, its acrylamide copolymer, and related DI- and trisaccharides for use in adhesion inhibition studies with Helicobacter pylori. J. Carbohydr. Chem. 15, 1161–1178 (1996)

    Article  CAS  Google Scholar 

  26. Pérez S.F., Lio R.G., Santana V.F., Bencomo V.V.: Synthesis of Lex and Ley oligosaccharides with azido-type spacer-arms. Comparison of 3- and 4-methoxybenzyl groups as key temporary protective groups. J. Carbohydr. Chem. 17, 835–850 (1998)

    Article  Google Scholar 

  27. Paulsen H., Kolar C.: Synthese der tetrasaccharid-ketten der type 2 der determinanten der blutgruppensubstanzen a und B. Tetrahedron Lett. 20, 2881–2884 (1979)

    Article  Google Scholar 

  28. Zhu T., Boons G.-J.: A highly efficient synthetic strategy for polymeric support synthesis of Lex, Ley, and H-type 2 oligosaccharides. Chem. Eur. J. 7, 2382–2389 (2001)

    Article  CAS  PubMed  Google Scholar 

  29. Ryzhov I.M., Korchagina E.Y., Popova I.S., Bovin N.V.: Block synthesis of a tetrasaccharides (types 1, 3, and 4) related to the human ABO blood group system. Carbohydr. Res. 351, 17–25 (2012)

    Article  CAS  PubMed  Google Scholar 

  30. Zierke M., Smiesko M., Rabbani S., Aeschbacher T., Cutting B., Allain F.H.T., Schubert M., Ernst B.: Stabilization of branched oligosaccharides: Lewisx benefits from a nonconventional C − H···O hydrogen bond. J. Am. Chem. Soc. 135, 13464–13472 (2013)

    Article  CAS  PubMed  Google Scholar 

  31. Hara A., Imamura A., Ando H., Ishida H., Kiso M.: A new chemical approach to human ABO histo-blood group type 2 antigens. Molecules. 19, 414–437 (2014)

    Article  Google Scholar 

  32. Corzana F., Bettler E., Herv’e du Penhoat C., Tyrtysh T.V., Bovin N.V., Imberty A.: Solution structure of two xenoantigens: α Gal-LacNac and α Gal-Lewis X. Glycobiology. 12, 241–250 (2002)

    Article  CAS  PubMed  Google Scholar 

  33. Compston C.A., Condon C., Hanna H.R., Mazid M.A.: Rapid production of a panel of blood group A-active oligosaccharides using chemically synthesized di- and tri-saccharide primers and an easily prepared porcine (1 → 3)-α-N-acetyl-D-galactosaminyltransferase. Carbohydr. Res. 239, 167–176 (1993)

    Article  CAS  PubMed  Google Scholar 

  34. Yi W., Shao J., Zhu L., Li M., Singh M., Lu Y., Lin S., Li H., Ryu K., Shen J., Guo H., Yao Q., Bush C.A., Wang P.G.: Escherichia coli O86 O-antigen biosynthetic gene cluster and stepwise enzymatic synthesis of human blood group B antigen tetrasaccharide. J. Am. Chem. Soc. 127, 2040–2041 (2005)

    Article  CAS  PubMed  Google Scholar 

  35. Mandal P.K., Branson T.R., Hayes E.D., Ross J.F., Gavín J.A., Daranas A.H., Turnbull W.B.: Towards a structural basis for the relationship between blood group and the severity of El Tor Cholera. Angew. Chem. Int. Ed. 51, 5143–5146 (2012)

    Article  CAS  Google Scholar 

  36. Bovin N.V.: Polyacrylamide-based glycoconjugates as tools in glycobiology. Glycoconjugate J. 15, 431–446 (1998)

    Article  CAS  Google Scholar 

  37. Hindsgaul O., Norberg T., Le Pendu J., Lemieux R.U.: Synthesis of type 2 human blood-group antigenic determinants. The H, X, and Y haptens and variations of the H type 2 determinant as probes for the combining site of the lectin I of Ulex europaeus. Carbohydr. Res. 109, 109–142 (1982)

    Article  CAS  PubMed  Google Scholar 

  38. Spohr U., Lemieux R.U.: Synthetic, conformational, and immunochemical studies of modified Lewis b and Y human blood-group determinants to serve as probes for the combining site of the lectin IV of Griffonia simplicifolia. Carbohydr. Res. 174, 211–237 (1988)

    Article  CAS  PubMed  Google Scholar 

  39. Byramova N.E., Tuzikov A.B., Tyrtysh T.V., Bovin N.V.: 1,6-anhydro-N-acetyl-β-D-glucosamine in oligosaccharide synthesis: II. The synthesis of the spacered Ley tetrasaccharide. Russ. J. Bioorg. Chem. 33, 99–109 (2007)

    Article  CAS  Google Scholar 

  40. Takeo K., Tei S.: Synthesis of lactodifucotetraose. Carbohydr. Res. 141, 159–164 (1985)

    Article  CAS  Google Scholar 

  41. Fernandez-Mayoralas A., Martin-Lomas M.: Synthesis of 3- and 2′-fucosyl-lactose and 3,2′-difucosyl-lactose from partially benzylated lactose derivatives. Carbohydr. Res. 154, 93–101 (1986)

    Article  CAS  Google Scholar 

  42. DeFrees S.A., Calif S.M.: “Sialyl Lex analogues as inhibitors of cellular adhesion” U.S. Patent. 5854 218 (1998)

  43. Lönn H.: Synthesis of a tri- and a hepta-saccharide which contain α-L-fucopyranosyl groups and are part of the complex type of carbohydrate moiety of glycoproteins. Carbohydr. Res. 139, 105–113 (1985)

    PubMed  Google Scholar 

  44. Veeneman G.H., van Leeuwen S.H., van Boom J.H.: Iodonium ion promoted reactions at the anomeric centre. II An efficient thioglycoside mediated approach toward the formation of 1,2-trans linked glycosides and glycosidic esters. Tetrahedron Lett. 31, 1331–1334 (1990)

    Article  CAS  Google Scholar 

  45. Konradsson P., Udodong U.E., Fraser-Reid B.: Iodonium promoted reactions of disarmed thioglycosides. Tetrahedron Lett. 31, 4313–4316 (1990)

    Article  CAS  Google Scholar 

  46. Dinkelaar J., de Jong A.R., van Meer R., Somers M., Lodder G., Overkleeft H.S., Codee J.D.C., van der Marel G.A.: Stereodirecting effect of the pyranosyl C-5 substituent in glycosylation reactions. J. Org. Chem. 74, 4982–4991 (2009)

    Article  CAS  PubMed  Google Scholar 

  47. Pearlman W.M.: Noble metal hydroxides on carbon nonpyrophoric dry catalysts. Tetrahedron Lett. 8, 1663–1664 (1967)

    Article  Google Scholar 

  48. Kalidasan K., Su Y., Wu X., Yao S.Q., Uttamchandani M.: Fluorescence-activated cell sorting and directed evolution of α-N-acetylgalactosaminidases using a quenched activity-based probe (qABP). Chem. Commun. 49, 7237–7239 (2013)

    Article  CAS  Google Scholar 

  49. Mandal P.K., Turnbull W.B.: Studies on the synthesis of Lewis-y oligosaccharides. Carbohydr. Res. 346, 2113–2120 (2011)

    Article  CAS  PubMed  Google Scholar 

  50. Kanie O., Crawley S.C., Palcic M.M., Hindsgaul O.: Acceptor-substrate recognition by N-acetylglucosaminyltransferase-V: critical role of the 4″-hydroxyl group in β-D-GlcpNAc-(1 → 2)-α-D-Manp(1 → 6)-β-D-Glcp-OR. Carbohydr. Res. 243, 139–164 (1993)

    Article  CAS  PubMed  Google Scholar 

  51. Kinzy W., Schmidt R.R.: Glycosylimidate, 16. Synthese des Trisaccharids aus der „Repeating Unit” des Kapselpolysaccharids von Neisseria meningitides (Serogruppe L). Liebigs Ann. Chem. 1985, 1537–1545 (1985)

    Article  Google Scholar 

  52. Bouchra M., Calinaud P., Gelas J.: A new method of orthoesterification, under kinetic control, at non-anomeric positions. Application to the D-glucose and D-mannose series and selective hydrolysis of the corresponding orthoesters. Carbohydr. Res. 267, 227–237 (1995)

    Article  CAS  Google Scholar 

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Acknowledgments

Author gratefully acknowledges financial support by Department of Science and Technology (DST), India under Fast Track Proposal Scheme for Young Scientists (CS-127/2012) and SAIF Division of CSIR-CDRI for providing the spectroscopic and analytical data. CDRI communication no. 9106.

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Authors and Affiliations

  1. Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute, BS-10/1, Sector 10, Jankipuram extension, Sitapur Road, P.O. Box 173, Lucknow, 226031, India

    Geeta Karki, Vijay Nath Mishra & Pintu Kumar Mandal

  2. Academy of Scientific and Innovative Research, New Delhi, 110001, India

    Pintu Kumar Mandal

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  1. Geeta Karki
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Karki, G., Mishra, V.N. & Mandal, P.K. An expeditious synthesis of blood-group antigens, ABO histo-blood group type II antigens and xenoantigen oligosaccharides with amino type spacer−arms. Glycoconj J 33, 63–78 (2016). https://doi.org/10.1007/s10719-015-9635-1

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