Synthesis of a Blocked Tetrasaccharide Related to the Repeating Unit of the Antigen from Shigella dysenteriae Type 9 in the Form of Its Methyl (R)-Pyruvate Ester and 2-(Trimethylsilyl)Ethyl Glycoside

Journal of Carbohydrate Chemistry

Volumn 22, Issue 7-8, 2003, Pages 521-535

  Roy, Samarpita ^a   Roy, Nirmolendu ^a  

^a DEPARTMENT OF MATERIALS SCIENCE   (India)

Author keywords

Shigella dysenteriae type 9; Synthesis; Tetrasaccharide derivative

Indexed keywords

BACTERIAL ANTIGEN; CARBOHYDRATE DERIVATIVE; DISACCHARIDE; ESTER DERIVATIVE; GALACTOSE; GLUCOSAMINE; GLYCOCONJUGATE; GLYCOSIDE; MANNOSE; PYRUVIC ACID DERIVATIVE; SILANE DERIVATIVE; SUCCINIMIDE DERIVATIVE; TRICHLOROACETIMIDIC ACID; TRIFLUOROMETHANESULFONIC ACID;

ADDITION REACTION; ARTICLE; CARBOHYDRATE SYNTHESIS; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL BINDING; PROTON NUCLEAR MAGNETIC RESONANCE; SHIGELLA DYSENTERIAE;

BACTERIA (MICROORGANISMS); SHIGELLA DYSENTERIAE;

EID: 0347478174     PISSN: 07328303     EISSN: None     Source Type: Journal    
DOI: 10.1081/CAR-120026456     Document Type: Article

References (28)

1. Robbins, J.B.; Schneerson, R.; Czu, S.C.; Pozsgay, V. Bacterial polysaccharide-protein conjugate vaccines. Pure Appl. Chem. 1999, 71, 745-754.
2. Dubois, E.P.; Robbins, J.B.; Pozsgay, V. Chemical approaches to bacterial vaccines. Synthesis of mycobacterial oligosaccharide-protein conjugates for use as serodiagnostics and immunogens. Bioorg. Med. Chem. Lett. 1996, 6, 1387-1392.
3. Pozsgay, V.; Glaudemans, C.P.J.; Robbins, J.B.; Schneerson, R. Synthesis of a tetrasaccharide donor corresponding to the O-specific polysaccharide of Shigella dysenteriae type 1. Carbohydr. Res. 1993, 244, 259-273.
4. Pozsgay, V. Synthetic Shigella vaccines: a carbohydrate protein conjugate with totally synthetic hexadecasaccharide haptens. Angew. Chem. Int. Ed. 1998, 37, 138-142.
5. Pozsgay, V. Synthesis of a hexadecasaccharide fragment of the O-polysaccharide of Shigella dysenteriae type 1. J. Am. Chem. Soc. 1995, 117, 6673-6681.
6. Paulsen, H.; Bünsch, H. Synthese der pentasaccharid-sequenz der repeating-unit der O-spezifischen seitenkette des lipopolysaccharides von Shigella dysenteriae. Tetrahedron Lett. 1981, 22, 47-50.
7. Mulard, L.A.; Ughetto-Monfrin, J. Linear synthesis of the methyl glycosides of tri, tetra-, and pentasaccharide fragments of the Shigella flexneri seroytpe 5a O-antigen. J. Carbohydr. Chem. 2000, 19, 503-526.
8. Costachel, C.; Sansonetti, P.J.; Mulard, L.A. Linear synthesis of the methyl glycosides of tetra-and pentasaccharide fragments specific for the Shigella flexneri serotype 2a O-antigen. J. Carbohydr. Chem. 2000, 19, 1131-1150.
9. Mukhopadhyay, B.; Roy, N. Synthesis of the pentasaccharide related to the repeating unit of the antigen from Shigella dysenteriae type 4 in the form of its methyl ester 2-(trimethylsilyl)ethyl glycoside. Carbohydr. Res. 2003, 338, 589-596.
10. Mukherjee, I.; Das, S.K.; Mukherjee, A.; Roy, N. Synthesis of the tetrasaccharide related to the repeating unit of the antigen from Shigella dysenteriae type 5. Carbohydr. Res. 2000, 325, 245-252.
11. Dmitriev, B.A.; Knirel, Y.A.; Vinogradov, E.V.; Kochetkov, N.K.; Gofman, I.L. Bacterial antigenic polysaccharides VII. Structure of the polysaccharide chain of Shigella dysenteriae type 9 lipopolysaccharide. Bioorg. Khim. 1978, 4, 40-46.
12. Pal, J.; Basu, S.; Rao, C.V.N. Immunochemical studies on Shigella dysenteriae Type 9 bacterial polysaccharide. Carbohydr. Res. 1983, 114, 123-135.
13. Janak, N.; Patil, J.R.; Bose, J.L. Synthesis of some aryl β-thioglycosides. Indian J. Chem. 1968, 7, 227-229.
14. Hanessian, S.; Lavallee, P. The preparation and synthetic utility of rert-butyl-diphenylsilyl ethers. Can. J. Chem. 1975, 53, 2975-2977.
15. Lipták, A.; Imre, J.; Nánási, P. Preparation of carbohydrate isopropylidene derivatives with 2,2-dimethoxypropane in the presence of toluene-p-sulphonic acid. Carbohydr. Res. 1981, 92, 154-156.
16. Yang, F.; He, H.; Du, Y. Synthesis of (1 → 6)-β-D-glucosamine hexasaccharide, a potential antitumor and immunostimulating agent. Tetrahedron Lett. 2002, 43, 7561-7563.
17. Posgay, V.; Coxon, B.; Yeh, H. Synthesis of di-to pentasaccharides related to the O-specific polysaccharide of Shigella dysenteriae type 1, and their nuclear magnetic resonance study. Bioorg. Med. Chem. 1993, 1, 237-257.
18. Evans, M.E. Methyl 4,6-O-benzylidene α-and β-D- glucopyranoside via acetal exchange. In Methods in Carbohydrate Chemistry; Whistler, R.L., BeMiller, J.N., Eds.; Academic Press: New York, 1980; Vol. 8, 313-315.
19. 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. 1993, 243, 139-164.
20. Ziegler, T.; Eckhardt, E.; Strayle, J.; Herzog, H. Synthesis of 5-aminopentyl 4,6-O-[(R)-1-carboxyethylidene]-β-D-galactopyranoside and its use as a ligand for the affinity chromatography of human serum amyloid P protein. Carbohydr. Res. 1994, 253, 167-183.
21. Garegg, P.J.; Jansson, P.-E.; Lindberg, B.; Lindh, F.; Lönngren, J. Configuration of the acetal carbon atom of pyruvic acid acetals in some bacterial polysaccharides. Carbohydr. Res. 1980, 78, 127-132.
22. Garegg, P.J.; Kvarnström, I.; Niklasson, A.; Niklasson, G.; Svensson, S.C.T. Partial substitution of thioglycosides by phase transfer catalysed benzoylation and benzylation. J. Carbohydr. Chem. 1993, 12, 933-953.
23. Pozsgay, V. Synthesis of glycocongugate vaccines against Shigella dysenteriae type 1. J. Org. Chem. 1998, 63, 5983-5999.
24. Weingart, R.; Schmidt, R.R. Can preferential β-mannoside formation with 4,6-O-benzylidene protected mannopyranosyl sulfoxide be reached with trichloroacetimidates? Tetrahedron Lett. 2000, 41, 8753-8758.
25. Jansson, K.; Ahlfors, S.; Frejd, T.; Kihlberg, J.; Magnusson, G. 2-(Trimethylsilyl)-ethyl glycosides. Synthesis, anomeric deblocking and transformation into 1,2-trans 1-O-acetyl sugars. J. Org. Chem. 1988, 53, 5629-5647.
26. Garegg, P.J.; Hultberg, H.; Wallin, S. A novel reductive ring-opening of carbohydrate benzylidene acetals. Carbohydr. Res. 1982, 108, 97-101.
27. Matsuo, I.; Isomura, M.; Ajisaka, K. Synthesis of an asperagine-linked core pentasaccharide by means of simultaneous inversion reaction. J. Carbohydr. Chem. 1999, 18, 841-850.
28. Veeneman, G.H.; van Leeuwen, S.H.; van Boom, J.H. Iodonium ion promoted reactions at the anomeric center. II. An efficient thioglycoside mediated approach towards the formation of 1,2-trans linked glycosides and glycosidic esters. Tetrahedron Lett. 1990, 31, 1331-1334.