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Synthesis 2009(15): 2584-2590
DOI: 10.1055/s-0029-1217401
DOI: 10.1055/s-0029-1217401
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of a Trisaccharide and a Tetrasaccharide from the Cell-Wall Lipopolysaccharides of Azospirillum brasilense S17
Further Information
Received
11 March 2009
Publication Date:
22 June 2009 (online)
Publication History
Publication Date:
22 June 2009 (online)
![](https://www.thieme-connect.de/media/synthesis/200915/lookinside/thumbnails/10.1055-s-0029-1217401-1.jpg)
Abstract
A trisaccharide containing a d-mannosamine moiety and a tetrasaccharide containing an l-rhamnan chain that are found in the cell walls of Azospirillum brasilense S17 were synthesized concisely and in excellent yields. The key features of the synthetic strategy were stereoselective glycosylations and a minimum number of protecting-group manipulations.
Key words
oligosaccharides - glycosylations - d-mannosamine - Azospirillum brasilense - rhizobacteria
-
1a
Okon Y.Vanderleyden J. ASM News 1997, 63: 366 -
1b
Fedonenko YP.Konnova ON.Zatonsky GV.Konnova SA.Kocharova NA.Zdorovenko EL.Ignatov VV. Carbohydr. Res. 2005, 340: 1259 -
1c
Fedonenko YP.Konnova ON.Zatonsky GV.Shashkov AS.Konnova SA.Zdorovenko EL.Ignatov VV.Knirel YA. Carbohydr. Res. 2004, 339: 1813 -
1d
Fedonenko YP.Zatonsky GV.Konnova SA.Zdorovenko EL.Ignatov VV. Carbohydr. Res. 2002, 337: 869 - 2
Bashan Y.Holgium G. Can. J. Microbiol. 1997, 43: 103 - 3
Tien TM.Gaskins MH.Hubbell DH. Appl. Environ. Microbiol. 1979, 37: 1016 -
4a
Jofré E.Lagares A.Mori G. FEMS Microbiol. Lett. 2004, 231: 267 -
4b
Burdman S.Okon Y.Jurkevitch E. Crit. Rev. Microbiol. 2000, 26: 91 -
4c
De Troch P.Vanderleyden J. Microbiol. Ecol. 1996, 32: 149 -
4d
Konnova SA.Makarov OE.Skvortsov IM.Ignatov VV. FEMS Microbiol. Lett. 1994, 118: 93 - 5
Fedonenko YP.Konnova ON.Zdorovenko EL.Konnova SA.Zatonsky GV.Shashkov AS.Ignatov VV.Knirel YA. Carbohydr. Res. 2008, 343: 810 - 6
Hall DM. Carbohydr. Res. 1980, 86: 158 - 7
Boken HB.Ekborg G.Lonngren J. Acta Chem. Scand., Ser. B. 1975, 29: 1085 - 8
Zuurmond HM.van der Klein PAM.van der Marel GA.van Boom JH. Tetrahedron 1993, 49: 6501 - 9
Sajtos F.Hajkó J.Kövér KE.Lipták A. Carbohydr. Res. 2001, 334: 253 - 10
Sarkar K.Mukherjee I.Roy N. J. Carbohydr. Chem. 2003, 22: 95 - 11
Garegg PJ.Hultberg H.Wallin S. Carbohydr. Res. 1982, 108: 97 - 12
Veeneman GH.Van Leeuwen SH.Zuurmond H.van Boom JH. J. Carbohydr. Chem. 1990, 9: 783 - 13
Veeneman GH.Gomes LJF.van Boom JH. Tetrahedron 1989, 45: 7433 - 14
Das SK.Roy N. Carbohydr. Res. 1996, 296: 275 -
15a
Veeneman GH.van Leeuwen SH.van Boom JH. Tetrahedron Lett. 1990, 31: 1331 -
15b
Konradsson P.Udodong UE.Fraser-Reid B. Tetrahedron Lett. 1990, 31: 4313 - 16
Mandal PK.McMurray JS. J. Org. Chem. 2007, 72: 6599 - 17
Pearlman WM. Tetrahedron Lett. 1967, 8: 1663