Synthesis of a trisaccharide and a tetrasaccharide from the cell-wall lipopolysaccharides of Azospirillum brasilense S17

Synthesis

Volumn , Issue 15, 2009, Pages 2584-2590

  Pandey, Shashi ^a   Ghosh, Samir ^b   Misra, Anup Kumar ^b  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

^b BOSE INSTITUTE   (India)

Author keywords

Azospirillum brasilense; D mannosamine; Glycosylations; Oligosaccharides; Rhizobacteria

Indexed keywords

AZOSPIRILLUM BRASILENSE; CELL WALLS; D-MANNOSAMINE; GLYCOSYLATIONS; GROUP MANIPULATIONS; KEY FEATURE; LIPOPOLYSACCHARIDES; MANNOSAMINE; RHIZOBACTERIA; STEREO-SELECTIVE; SYNTHETIC STRATEGIES; TETRASACCHARIDES;

CELL MEMBRANES; OLIGOSACCHARIDES; POLYSACCHARIDES;

SYNTHESIS (CHEMICAL);

ETHYL 3,4 DI O BENZYL 2 O METHYL 1 THIO ALPHA RHAMNOPYRANOSIDE; LIPOPOLYSACCHARIDE; MANNOSAMINE; METHYL (2 ACETAMIDO 2 DEOXY BETA D GLUCOPYRANOSYL) (1 4) [(2 O METHYL ALPHA RHAMNOPYRANOSYL) (1 3)] 2 ACETAMIDO 2 DEOXY ALPHA MANNOPYRANOSIDE; METHYL (2 ACETAMIDO 3,4,6 TRI O ACETYL 2 DEOXY BETA D GLUCOPYRANOSYL) (1 4) [(3,4 DI O BENZYL 2 O METHYL ALPHA RHAMNOPYRANOSYL) (1 3)] 2 ACETAMIDO 6 O ACETYL 2 DEOXY ALPHA MANNOPYRANOSIDE; METHYL (2,3,4 TRI O ACETYL ALPHA RHAMNOPYRANOSYL) (1 3) (2 O ALLYL 4 O BENZYL ALPHA RHAMNOPYRANOSYL) (1 3) 2,4 DI O BENZYL ALPHA RHAMNOPYRANOSIDE; METHYL (2,3,4 TRI O ACETYL ALPHA RHAMNOPYRANOSYL) (1 3) (4 O BENZYL ALPHA RHAMNOPYRANOSYL) (1 3) 2,4 DI O BENZYL ALPHA RHAMNOPYRANOSIDE; METHYL (2,3,4 TRI O ACETYL ALPHA RHAMNOPYRANOSYL) (1 3) [(2,3,4,6 TETRA O ACETYL BETA D GLUCOPYRANOSYL) (1 2)] (4 O BENZYL ALPHA RHAMNOPYRANOSYL) (1 3) 2,4 DI O BENZYL ALPHA RHAMNOPYRANOSIDE; METHYL (ALPHA RHAMNOPYRANOSYL) (1 3) [(BETA GLUCOPYRANOSYL) (1 2)] (ALPHA RHAMNOPYRANOSYL) (1 3) ALPHA RHAMNOPYRANOSIDE; METHYL 2 AZIDO 3 O BENZYL 4,6 O BENZYLIDENE 2 DEOXY ALPHA D MANNOPYRANOSIDE; METHYL 2 AZIDO 6 O BENZOYL 3 O BENZYL 2 DEOXY ALPHA D MANNOPYRANOSIDE; METHYL 3 (2 O ALLYL 4 O BENZYL ALPHA RHAMNOPYRANOSYL) 2,4 DI O BENZYL ALPHA RHAMNOPYRANOSIDE; METHYL 3 (2,3 DI O ACETYL 4 O BENZYL ALPHA RHAMNOPYRANOSYL) 2,4 DI O BENZYL ALPHA RHAMNOPYRANOSIDE; METHYL 4 (2 ACETAMIDO 3,4,6 TRI O ACETYL 2 DEOXY BETA D GLUCOPYRANOSYL) 2 ACETAMIDO 6 O ACETYL 2 DEOXY ALPHA D MANNOPYRANOSIDE; TETRASACCHARIDE; TRISACCHARIDE; UNCLASSIFIED DRUG;

ARTICLE; AZOSPIRILLUM BRASILENSE; CELL WALL; CHEMICAL REACTION; CHEMICAL STRUCTURE; GLYCOSYLATION; NONHUMAN; STEREOCHEMISTRY; SYNTHESIS;

EID: 69849091829     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1217401     Document Type: Article

References (24)

1. (a) Okon, Y.; Vanderleyden, J. ASM News 1997, 63, 366.
2. (b) Fedonenko, Y. P.; Konnova, O. N.; Zatonsky, G. V.; Konnova, S. A.; Kocharova, N. A.; Zdorovenko, E. L.; Ignatov, V. V. Carbohydr. Res. 2005, 340, 1259.
3. (c) Fedonenko, Y. P.; Konnova, O. N.; Zatonsky, G. V.; Shashkov, A. S.; Konnova, S. A.; Zdorovenko, E. L.; Ignatov, V. V.; Knirel, Y. A. Carbohydr. Res. 2004, 339, 1813.
4. (d) Fedonenko, Y. P.; Zatonsky, G. V.; Konnova, S. A.; Zdorovenko, E. L.; Ignatov, V. V. Carbohydr. Res. 2002, 337, 869.
5. Bashan, Y.; Holgium, G. Can. J. Microbiol. 1997, 43, 103.
6. Tien, T. M.; Gaskins, M. H.; Hubbell, D. H. Appl. Environ. Microbiol. 1979, 37, 1016.
7. (a) Jofré, E.; Lagares, A.; Mori, G. FEMS Microbiol. Lett. 2004, 231, 267.
8. (b) Burdman, S.; Okon, Y.; Jurkevitch, E. Crit. Rev. Microbiol. 2000, 26, 91.
9. (c) De Troch, P.; Vanderleyden, J. Microbiol. Ecol. 1996, 32, 149.
10. (d) Konnova, S. A.; Makarov, O. E.; Skvortsov, I. M.; Ignatov, V. V. FEMS Microbiol. Lett. 1994, 118, 93.
11. Fedonenko, Y. P.; Konnova, O. N.; Zdorovenko, E. L.; Konnova, S. A.; Zatonsky, G. V.; Shashkov, A. S.; Ignatov, V. V.; Knirel, Y. A. Carbohydr. Res. 2008, 343, 810.
12. Hall, D. M. Carbohydr. Res. 1980, 86, 158.
13. Boken, H. B.; Ekborg, G.; Lonngren, J. Acta Chem. Scand., Ser. B. 1975, 29, 1085.
14. Zuurmond, H. M.; van der Klein, P. A. M.; van der Marel, G. A.; van Boom, J. H. Tetrahedron 1993, 49, 6501.
15. Sajtos, F.; Hajkó, J.; Kövér, K. E.; Lipták, A. Carbohydr. Res. 2001, 334, 253.
16. Sarkar, K.; Mukherjee, I.; Roy, N. J. Carbohydr. Chem. 2003, 22, 95.
17. Garegg, P. J.; Hultberg, H.; Wallin, S. Carbohydr. Res. 1982, 108, 97.
18. Veeneman, G. H.; Van Leeuwen, S. H.; Zuurmond, H.; van Boom, J. H. J. Carbohydr. Chem. 1990, 9, 783.
19. Veeneman, G. H.; Gomes, L. J. F.; van Boom, J. H. Tetrahedron 1989, 45, 7433.
20. Das, S. K.; Roy, N. Carbohydr. Res. 1996, 296, 275.
21. (a) Veeneman, G. H.; van Leeuwen, S. H.; van Boom, J. H. Tetrahedron Lett. 1990, 31, 1331.
22. (b) Konradsson, P.; Udodong, U. E.; Fraser-Reid, B. Tetrahedron Lett. 1990, 31, 4313.
23. Mandal, P. K.; McMurray, J. S. J. Org. Chem. 2007, 72, 6599.
24. Pearlman, W. M. Tetrahedron Lett. 1967, 8, 1663.