Efficient Routes Toward the Synthesis of the D-rhamno-trisaccharide Related to the A-band Polysaccharide of Pseudomonas Aeruginosa

Overview

Journal Beilstein J Org Chem

Specialty Chemistry

Date 2014 Aug 28

PMID 25161705

Citations 3

Authors

Aritra Chaudhury

Sajal K Maity

Rina Ghosh

Affiliations

Soon will be listed here.

Abstract

The present work describes efficient avenues for the synthesis of the trisaccharide repeating unit [α-D-Rhap-(1→3)-α-D-Rhap-(1→3)-α-D-Rhap] associated with the A-band polysaccharide of Pseudomonas aeruginosa. One of the key steps involved 6-O-deoxygenation of either partially or fully acylated 4,6-O-benzylidene-1-thiomannopyranoside by radical-mediated redox rearrangement in high yields and regioselectivity. The D-rhamno-thioglycosides so obtained allowed efficient access to the trisaccharide target via stepwise glycosylation as well as a one-pot glycosylation protocol. In a different approach, a 4,6-O-benzylidene D-manno-trisaccharide derivative was synthesized, which upon global 6-O-deoxygenation followed by deprotection generated the target D-rhamno-trisaccharide. The application of the reported regioselective radical-mediated deoxygenation on 4,6-O-benzylidene D-manno thioglycoside (hitherto unexplored) has potential for ramification in the field of synthesis of oligosaccharides based on 6-deoxy hexoses.

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References

Crich D, Bowers A . 4,6-O-[1-cyano-2-(2-iodophenyl)ethylidene] acetals. improved second-generation acetals for the stereoselective formation of beta-D-mannopyranosides and regioselective reductive radical fragmentation to beta-D-rhamnopyranosides. scope and limitations. J Org Chem. 2006; 71(9):3452-63. PMC: 4664482. DOI: 10.1021/jo0526688. View

Shivatare S, Chang S, Tsai T, Ren C, Chuang H, Hsu L . Efficient convergent synthesis of bi-, tri-, and tetra-antennary complex type N-glycans and their HIV-1 antigenicity. J Am Chem Soc. 2013; 135(41):15382-91. DOI: 10.1021/ja409097c. View

Yokota S, Kaya S, Sawada S, Kawamura T, Araki Y, Ito E . Characterization of a polysaccharide component of lipopolysaccharide from Pseudomonas aeruginosa IID 1008 (ATCC 27584) as D-rhamnan. Eur J Biochem. 1987; 167(2):203-9. DOI: 10.1111/j.1432-1033.1987.tb13324.x. View

Bedini E, Carabellese A, Barone G, Parrilli M . First synthesis of the beta-D-rhamnosylated trisaccharide repeating unit of the O-antigen from Xanthomonas campestris pv. campestris 8004. J Org Chem. 2005; 70(20):8064-70. DOI: 10.1021/jo051153d. View

Kocharova N, Borisova S, Zatonsky G, Shashkov A, Knirel Y, KHOLODKOVA E . Structure of the O-specific polysaccharide of Citrobacter freundii O3a,3b,1c. Carbohydr Res. 1998; 306(1-2):331-3. DOI: 10.1016/s0008-6215(97)10049-0. View

Basu N, Maity S, Chaudhury A, Ghosh R . Trichloroisocyanuric acid (TCCA): an efficient green reagent for activation of thioglycosides toward hydrolysis. Carbohydr Res. 2013; 369:10-3. DOI: 10.1016/j.carres.2013.01.001. View

Hsu C, Hung S, Wu C, Wong C . Toward automated oligosaccharide synthesis. Angew Chem Int Ed Engl. 2011; 50(50):11872-923. DOI: 10.1002/anie.201100125. View

Crich D, Li L . Stereocontrolled synthesis of D- and L-beta-rhamnopyranosides with 4-O-6-S-alpha-cyanobenzylidene-protected 6-thiorhamnopyranosyl thioglycosides. J Org Chem. 2009; 74(2):773-81. PMC: 2696688. DOI: 10.1021/jo8022439. View

Hullar T, Siskin S . The facile bromination by N-bromosuccinimide of benzylidene acetals of carbohydrates. Application to the synthesis of 2,6-imino carbohydrates (substituted 2,5-oxazabicyclo[2.2.2]octanes). J Org Chem. 1970; 35(1):225-8. DOI: 10.1021/jo00826a046. View

10.

Tsvetkov Y, Backinowsky L, Kochetkov N . Synthesis of a common polysaccharide antigen of Pseudomonas aeruginosa as the 6-aminohexyl glycoside. Carbohydr Res. 1989; 193:75-90. DOI: 10.1016/0008-6215(89)85108-0. View

11.

Herasimenka Y, Cescutti P, Impallomeni G, Campana S, Taccetti G, Ravenni N . Exopolysaccharides produced by clinical strains belonging to the Burkholderia cepacia complex. J Cyst Fibros. 2006; 6(2):145-52. DOI: 10.1016/j.jcf.2006.06.004. View

12.

Picard S, Crich D . Synthesis of the beta-rhamnopyranosides and the 6-deoxy-beta-mannoheptopyranosides. Chimia (Aarau). 2011; 65(1-2):59-64. DOI: 10.2533/chimia.2011.59. View

13.

Senchenkova S, Shashkov A, Knirel Y, McGOVERN J, Moran A . The O-specific polysaccharide chain of Campylobacter fetus serotype B lipopolysaccharide is a D-rhamnan terminated with 3-O-methyl-D-rhamnose (D-acofriose). Eur J Biochem. 1996; 239(2):434-8. DOI: 10.1111/j.1432-1033.1996.0434u.x. View

14.

Varki A . Biological roles of oligosaccharides: all of the theories are correct. Glycobiology. 1993; 3(2):97-130. PMC: 7108619. DOI: 10.1093/glycob/3.2.97. View

15.

Fuster M, Esko J . The sweet and sour of cancer: glycans as novel therapeutic targets. Nat Rev Cancer. 2005; 5(7):526-42. DOI: 10.1038/nrc1649. View

16.

Faure R, Shiao T, Lagnoux D, Giguere D, Roy R . En route to a carbohydrate-based vaccine against Burkholderia cepacia. Org Biomol Chem. 2007; 5(16):2704-8. DOI: 10.1039/b708365c. View

17.

Crich D, Bowers A . Synthesis of a beta-(1-->3)-D-rhamnotetraose by a one-pot, multiple radical fragmentation. Org Lett. 2006; 8(19):4327-30. PMC: 2617736. DOI: 10.1021/ol061706m. View

18.

Nicolaou K, Mitchell H . Adventures in Carbohydrate Chemistry: New Synthetic Technologies, Chemical Synthesis, Molecular Design, and Chemical Biology A list of abbreviations can be found at the end of this article. Telemachos Charalambous was an inspiring teacher at the.... Angew Chem Int Ed Engl. 2001; 40(9):1576-1624. View

19.

Crich D, Yao Q . Benzylidene acetal fragmentation route to 6-deoxy sugars: direct reductive cleavage in the presence of ether protecting groups, permitting the efficient, highly stereocontrolled synthesis of beta-D-rhamnosides from D-mannosyl glycosyl donors. Total.... J Am Chem Soc. 2004; 126(26):8232-6. DOI: 10.1021/ja048070j. View

20.

Winn A, Wilkinson S . Structure of the O20 antigen of Stenotrophomonas (Xanthomonas or Pseudomonas) maltophilia. Carbohydr Res. 1996; 294:109-15. DOI: 10.1016/s0008-6215(96)90623-0. View