Synthesis of β-D-Glcp-(1→2)-[β-D-Ribf-(1→3)-]α-L-Rhap- (1→3)-α-L-Rhap-(1→2)-α-L-Rhap, the repeating unit of the lipopolysaccharide of Acetobacter diazotrophicus PAL 5

Journal of Carbohydrate Chemistry

Volumn 21, Issue 6, 2002, Pages 579-589

  Zhang, Jianjun ^a   Kong, Fanzuo ^a  

^a RESEARCH CENTER FOR ECO ENVIRONMENTAL SCIENCES   (China)

Author keywords

Regio and stereoselective synthesis; Rhamnan; Trichloroacetimidate

Indexed keywords

CARBOHYDRATE DERIVATIVE; DISACCHARIDE; GLUCOSE DERIVATIVE; GLYCOSIDE; LIPOPOLYSACCHARIDE; PENTASACCHARIDE; PYRANOSIDE; TRICHLOROACETIMIDIC ACID; TRISACCHARIDE;

ACETOBACTER DIAZOTROPHICUS; ACETYLATION; ARTICLE; BENZOYLATION; CARBOHYDRATE SYNTHESIS; CHEMICAL REACTION; CONTROLLED STUDY; DEACETYLATION; DEALLYLATION; DEPROTECTION REACTION; GLYCOSYLATION; NONHUMAN; POLYMERIZATION; STEREOCHEMISTRY;

ACETOBACTER; BACTERIA (MICROORGANISMS); GLUCONACETOBACTER DIAZOTROPHICUS;

EID: 0036925442     PISSN: 07328303     EISSN: None     Source Type: Journal    
DOI: 10.1081/CAR-120016856     Document Type: Article

References (10)

1. Previato, J.O.; Jones, C.; Stephan, M.P.; Almeida, L.P.A.; Mendonca-Previato, L. Structures of the repeating oligosaccharide from the lipopolysaccharide of the nitrogen-fixing bacterium Acetobacter diazotrophicus strain PAL 5. Carbohydr. Res. 1997, 298, 311-318.
2. Lima, E.; Boddey, R.M.; Döbereiner, J. Quantification of biological nitrogen fixation associated with sugar cane using a nitrogen-15 aided nitrogen balance. Soil Biol. Biochem. 1987, 19, 165-170.
3. Battisti, L.; Lara, J.C.; Leigh, J.A. Specific succinoglycan plays an important role in root nodulation development. Proc. Natl. Acad. Sci. U. S. A. 1992, 89, 5625-5629.
4. Marino-Albernas, J.; Harris, S.L.; Varma, V.; Pinto, B.M. Convergent synthesis of an elusive hexasaccharide corresponding to the cell-wall polysaccharide of the β-hemolytic Streptococcus Group A. Carbohydr. Res. 1993, 298, 245-257.
5. Wang, W.; Kong, F. Highly regio- and steroselective synthesis of mannose-containing oligosaccharides with acetobromo sugars as the donors and partially protected mannose derivatives as the acceptors via sugar orthoester intermediates. Angew. Chem., Int. Ed. 1999, 38, 1247-1250.
6. Wang, W.; Kong, F. New synthetic methodology for regio-and stereoselective synthesis of oligosaccharides via sugar orthoester intermediates. J. Org. Chem. 1998, 63, 5744-5755.
7. Du, Y.; Kong, F. Regio- and stereoselective synthesis of rhamnose-containing oligosaccharides via sugar-sugar orthoester formation and rearrangement. J. Carbohydr. Chem. 1999, 18 655-664.
8. Zhu, Y.; Kong, F. Synthesis of α-(1→6)-linked mannose dodecasaccharide and β-(1→6)-linked glucooctaose using sugar trichloroacetimidates as the donor and unprotected and partially protected glycosides as the acceptors. Synlett 2000, 663-669.
9. Chiu-Machado, I.; Castro-Palomino, J.C.; Madrazo-Aloso, O.; Loipeteguipalucious, C.; Verez-Bencomo, V. Synthesis of ribofuranosides by catalysis with Lewis acids. Glycosidation versus transacetylation. J. Carbohydr. Chem. 1995, 14, 551-561.
10. Schmidt, R.R.; Kinzy, W. Anomeric-oxygen activation for glycoside synthesis: The trichloroacetimidate method. Adv. Carbohydr. Chem. Biochem. 1994, 50, 21-125.