Synthesis of oligosaccharide fragments corresponding to the exopolysaccharide released by Streptococcus macedonicus Sc 136

Glycoconjugate Journal

Volumn 25, Issue 2, 2008, Pages 85-99

  Tiwari, Pallavi ^a   Misra, Anup Kumar ^a  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

Anomeric control; Carbohydrates; Exopolysaccharides; Glycosides; Glycosylations

Indexed keywords

EXOPOLYSACCHARIDE; METHYL (2,3,4,6 TETRA O ACETYL BETA DEXTRO GALACTOPYRANOSYL METHYL (2,3,4,6 TETRA O ACETYL BETA DEXTRO GALACTOPYRANOSYL) 2,3,6 TRI O BENZYL BETA DEXTRO GLUCOPYRANOSIDE; METHYL (2,6 DI O BENZYL 3,4 O ISOPROPYLIDENE BETA DEXTRO GALACTOPYRANOSYL) (1-4) (2,3,6 TRI O BENZYL BETA DEXTRO GLUCOPYRANOSYL) (1-4) 2,3,6 TRI O BENZYL BETA DEXTRO GLUCOPYRANOSIDE; METHYL (2,6 DI O BENZYL BETA DEXTRO GALACTOPYRANOSYL) (1-4) (2,3,6 TRI O BENZYL BETA DEXTRO GLUCOPYRANOSYL) (1-4) 2,3,6 TRI O BENZYL ALPHA DEXTRO GLUCOPYRANOSIDE; METHYL (4 O ACETYL 2,6 DI O BENZYL BETA DEXTRO GALACTOPYRANOSYL) (1-4) (2,3,6 TRI O BENZYL BETA DEXTRO GLUCOPYRANOSYL) (1-4) 2,3,6 TRI O BENZYL ALPHA DEXTRO GLUCOPYRANOSIDE; METHYL (BEETA DEXTRO GALACTOFURANOSYL) (1-6) (BETA DEXTRO GLUCOPYRANOSYL) (1-6) (2 ACETAMIDO 2 DEOXY BETA DEXTRO GLUCOPYRANOSYL) (1-3) (BETA DEXTRO GALACTOPYRANOSYL) (1-4) BETA DEXTRO GLUCOPYRANOSIDE; METHYL [(2 ACETAMIDO 2 DEOXY BETA DEXTRO GLUCOPYRANOSYL) (1-3)] (ALPHA DEXTRO GLUCOPYRANOSYL) (1-4) (BETA DEXTRO GALACTOPYRANOSYL) (1-4) BETA DEXTRO GLUCOPYRANOSIDE; OLIGOSACCHARIDE; UNCLASSIFIED DRUG;

ARTICLE; CARBOHYDRATE SYNTHESIS; DRUG SYNTHESIS; GLYCOSYLATION; NONHUMAN; PRIORITY JOURNAL; STREPTOCOCCUS; STREPTOCOCCUS MACEDONICUS SC 136;

CARBOHYDRATE SEQUENCE; GLYCOSYLATION; MOLECULAR SEQUENCE DATA; OLIGOSACCHARIDES; POLYSACCHARIDES, BACTERIAL; STREPTOCOCCUS;

STREPTOCOCCUS MACEDONICUS;

EID: 39049110124     PISSN: 02820080     EISSN: 15734986     Source Type: Journal    
DOI: 10.1007/s10719-007-9056-x     Document Type: Article

References (34)

1. Fuller, R.: Probiotics in man and animals. J. Appl. Bacteriol. 66, 365-378 (1989)
2. Maldonado, Galdeano C. Perdigon, G.: Role of viability of probiotic strains in their persistence in the gut and in mucosal immune stimulation. J. Appl. Microbiol. 97, 673-681 (2004)
3. Mater, D.G., Bretigny, L., Firmesse, O., Flores, M.J., Mogenet, A., Bresson, J.L., Corthier, G.: Streptococcus thermophilus and Lactobacillus delbrueckii subsp. bulgaricus survive gastrointestinal transit of healthy volunteers consuming yogurt. FEMS Microbiol. Lett. 250, 185-187 (2005)
4. Sutherland, I.W.: Bacterial exopolysaccharides. Adv. Microbiol. Physiol. 8, 143-213 (1972)
5. Sutherland, I.W.: Novel and established applications of microbial polysaccharides. Trends Biotechnol. 16, 41-46 (1998)
6. Cerning, J.: Exocellular polysaccharides produced by lactic acid bacteria. FEMS Microbiol. Rev. 87, 113-130 (1990)
7. Whitfield, C., Keenleyside, W.J.: Regulation of expression of group IA capsular polysaccharides in Escherichia coli and related extracellular polysaccharides in other bacteria. J. Ind. Microbiol. 15, 361-371 (1995)
8. Roberts, I.S.: Bacterial polysaccharides in sickness and in health. The 1995 Fleming Lecture. Microbiology 141, 2023-2031 (1995)
9. Kitazawa, H., Watanabe, H., Shimosato, T., Kawai, Y., Itoh, T., Saito, T.: Immunostimulatory oligonucleotide, CpG-like motif exists in Lactobacillus delbrueckii ssp. bulgaricus NIAI B6. Int. J. Food Microbiol. 85, 11-21 (2003)
10. Danielson, A.D. Peo, E.R. Shahani, K.M. Lewis, A.J. Whalen, P.J. Amer, M.A.: Anticholesteremic property of Lactobacillus acidophilus yogurt fed to mature boars. J. Anim. Sci. 67, 966-974 (1989)
11. Gilliland, S.E. Nelson, C.R. Maxwell, C.: Assimilation of cholesterol by Lactobacillus acidophilus. Appl. Environ. Microbiol. 49, 377-381 (1985)
12. Savaiano, D.A. Levitt, M.D.: Nutritional and therapeutic aspects of fermented dairy products. ASDC J. Dent. Child. 51, 305-308 (1984)
13. Bodana, A.R., Rao, D.R.: Antimutagenic activity of milk fermented by Streptococcus thermophilus and Lactobacillus bulgaricus. J. Dairy Sci. 73, 3379-3384 (1990)
14. Welman, A.D., Maddox, I.S.: Exopolysaccharides from lactic acid bacteria: perspectives and challenges. Trends Biotechnol. 21, 269-274 (2003)
15. Miteva, V., Ivanova, I., Budakov, I., Pantev, A., Stefanova, T., Danova, S., Moncheva, P., Mitev, V., Dousset, X., Boyaval, P.: Detection and characterization of a novel antibacterial substance produced by a Lactobacillus delbrueckii strain 1043. J. Appl. Microbiol. 85, 603-614 (1998)
16. Hassan, A.N., Frank, J.F., Shalabi, S.I.: Factors affecting capsule size and production by lactic acid bacteria used as dairy starter cultures. Int. J. Food Microbiol. 64, 199-203 (2001)
17. Vincent, S.J.F., Faber, E.J., Neeser, J.R., Stingele, F., Kamerling, J.P.: Structure and properties of the exopolysaccharide produced by Streptococcus macedonicus Sc136. Glycobiology. 2, 131-139 (2001)
18. Tomoo, T., Kondo, T., Abe, H., Tsukamoto, S., Isobe, M., Goto, T.: An efficient short-step total synthesis of ganglioside GM3: effective usage of the neighbouring group participation strategy. Carbohydr. Res. 284, 207-222 (1996)
19. Sarkar, K., Mukherjee, I., Roy, N.: Synthesis of the trisaccharide repeating unit of the O-antigen related to the enterohemorrhagic Escherichia coli type O26:H. J. Carbohydr. Chem. 22, 95-107 (2003)
20. Kihlberg, J.O., Leigh, D.A., Bundle, D.R.: The in situ activation of thioglycosides with bromine: an improved glycosylation method. J. Org. Chem. 55, 2860-2863 (1990)
21. Dasgupta, F., Garegg, P.J.: Synthesis of ethyl and phenyl 1-thio-1,2-trans-d-d-glucopyranosides from the corresponding per-O-acetylated glycopyranoses having a 1,2-trans configuration using ferric chloride as a promoter. Acta Chem Scand. 43, 471-475 (1989)
22. 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. 253, 167-183 (1994)
23. Ferrieres, V., Roussel, M., Gelin, M., Plusquellec, D.: A new approach to a disaccharidic hapten containing a galactofuranosyl entity. J. Carbohydr. Chem. 9, 855-865 (2001)
24. Mallet, J.M., Meyer, G., Yvelin, F., Jutand, A., Amatore, C., Sinaÿ, P.: Electrosyntheses of disaccharides from phenyl or ethyl 1-thioglycosides Carbohydr.Res. 244, 237-246 (1993)
25. Ohlsson, J., Magnusson, G.: Galabiosyl donors; efficient synthesis from 1,2,3,4,6-penta-O-acetyl-β-d-galactopyranose. Carbohydr. Res. 329, 49-55 (2000)
26. Bergonzi, M.C., Catelani, G.D., Andrea, F., De Rensis, F.: The acetonation of methyl 5-C-methoxy-β-d-galactopyranoside with 2,2-dimethoxypropane. Carbohydr. Res. 311, 231-234 (1998)
27. Madhusudan, S.K., Agnihotri, G., Negi, D.S., Misra, A.K.: Direct one-pot conversion of acylated carbohydrates into their alkylated derivatives under heterogeneous reaction conditions using solid NaOH and a phase transfer catalyst. Carbohydr. Res. 340, 1373-1377 (2005)
28. Lewbart, M.L., Schneider, J.J.: Preparation and properties of steroidal 17,20- and 20,21-acetonides epimeric at C-20. I. Derivatives of 5.beta.-pregnan-3.alpha.-ol. J. Org. Chem. 34, 3505-3512 (1969)
29. 1H NMR characterization of the six isomeric mono-O-sulfates of 8-methoxycarbonyloct-1-yl O-β-d-galactopyranosyl-(1→4)-2-acetamido-2- deoxy-β-d-glucopyranoside. Carbohydr. Res. 276, 347-363 (1995)
30. 2 and direct conversion of acetals to acetates. Tetrahedron Lett. 47, 3653-3658 (2006)
31. Lee, H.-H., Schwartz, D.A., Harris, J.F., Carver, J.P., Krepinsky, J.J.: Syntheses of model oligosaccharides of biological significance. 7. Synthesis of a fucosylated N,N′-diacetylchitobioside linked to bovine serum albumin and immunochemical characterization of rabbit antisera to this structure. Can. J. Chem. 64, 1912-1918 (1986)
32. Perlman, W.M.: Noble metal hydroxides on carbon nonpyrophoric dry catalysts. Tetrahedron Lett. 8, 1663-1664 (1967)
33. 13C-enriched compounds. Carbohydr. Res. 100, 87-101 (1982)
34. Gibson, G.R., Roberfroid, M.B.: Dietary modulation of the human colonic microbiota: Introducing the concept of prebiotics. J. Nutr. 125, 1401-1412 (1995)