An expeditious synthesis of blood-group antigens, ABO histo-blood group type II antigens and xenoantigen oligosaccharides with amino type spacer−arms
详细信息 查看全文
- 作者：Geeta Karki ; Vijay Nath Mishra ; Pintu Kumar Mandal
- 关键词：Blood group antigen ; Oligosaccharide ; Glycosylation ; Xenoantigen ; Aminopropyl
- 刊名：Glycoconjugate Journal
- 出版年：2016
- 出版时间：February 2016
- 年：2016
- 卷：33
- 期：1
- 页码：63-78
- 全文大小：1,035 KB
- 参考文献：1.Watkins W.M., Morgan W.T.J.: Specific inhibition studies relating to the Lewis blood-group system. Nature. 180, 1038–1040 (1957)CrossRef PubMed
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)PubMed
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)CrossRef
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)PubMed
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)CrossRef PubMed
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)CrossRef PubMed
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
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)PubMed
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)CrossRef PubMed
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)CrossRef
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)PubMedCentral CrossRef PubMed
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)CrossRef PubMed
13.Mall A.S.: Analysis of mucins: role in laboratory diagnosis. J. Clin. Pathol. 61, 1018–1024 (2008)CrossRef PubMed
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)CrossRef PubMed
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
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)CrossRef PubMed
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)CrossRef
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)PubMed
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)CrossRef PubMed
20.Meloncelli P.J., Lowary T.L.: Synthesis of ABO histo-blood group type I and II antigens. Carbohydr. Res. 345, 2305–2322 (2010)CrossRef PubMed
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)CrossRef
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)CrossRef
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)CrossRef
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)CrossRef
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)CrossRef
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)CrossRef
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)CrossRef
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)CrossRef PubMed
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)CrossRef PubMed
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)CrossRef PubMed
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)CrossRef
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)CrossRef PubMed
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)CrossRef PubMed
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)CrossRef PubMed
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)CrossRef
36.Bovin N.V.: Polyacrylamide-based glycoconjugates as tools in glycobiology. Glycoconjugate J. 15, 431–446 (1998)CrossRef
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)CrossRef PubMed
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)CrossRef PubMed
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)CrossRef
40.Takeo K., Tei S.: Synthesis of lactodifucotetraose. Carbohydr. Res. 141, 159–164 (1985)CrossRef
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)CrossRef
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
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)CrossRef
45.Konradsson P., Udodong U.E., Fraser-Reid B.: Iodonium promoted reactions of disarmed thioglycosides. Tetrahedron Lett. 31, 4313–4316 (1990)CrossRef
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)CrossRef PubMed
47.Pearlman W.M.: Noble metal hydroxides on carbon nonpyrophoric dry catalysts. Tetrahedron Lett. 8, 1663–1664 (1967)CrossRef
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)CrossRef
49.Mandal P.K., Turnbull W.B.: Studies on the synthesis of Lewis-y oligosaccharides. Carbohydr. Res. 346, 2113–2120 (2011)CrossRef PubMed
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)CrossRef PubMed
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)CrossRef
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)CrossRef - 作者单位：Geeta Karki (1)
Vijay Nath Mishra (1)
Pintu Kumar Mandal (1) (2)
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
2. Academy of Scientific and Innovative Research, New Delhi, 110001, India - 刊物类别：Biomedical and Life Sciences
- 刊物主题：Life Sciences
Biochemistry
Pathology - 出版者：Springer Netherlands
- ISSN：1573-4986
文摘
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. Keywords Blood group antigen Oligosaccharide Glycosylation Xenoantigen Aminopropyl