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Synthesis 2014; 46(14): 1947-1953
DOI: 10.1055/s-0033-1341256
DOI: 10.1055/s-0033-1341256
paper
Concise Synthesis of the Repeating Units of the Cell Wall Lipopolysaccharide of Azospirillum brasilense SR80
Further Information
Publication History
Received: 08 November 2013
Accepted after revision: 31 March 2014
Publication Date:
13 May 2014 (online)
Abstract
Syntheses of trisaccharide and tetrasaccharide repeating units of the cell wall lipopolysaccharide of Azospirillum brasilense SR80 as their 4-methoxyphenyl (PMP) glycosides have been achieved following a sequential glycosylation strategy in good yield. All intermediate steps are high-yielding and the glycosylation steps are highly stereoselective.
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References
- 1a Bekri MA, Desair J, Proost P, Leeuwen MS.-V, Vanderleyden J, Vande Broek A. J. Bacteriol. 1999; 182: 2440
- 1b Okon Y. Trends Biotechnol. 1985; 3: 223
- 1c Steenhoudt O, Vanderleyden J. FEMS Microbiol. Rev. 2000; 24: 487
- 2a Das AJ, Kumar M, Kumar R. Res. J. Agriculture Forestry Sci. 2013; 1: 21
- 2b Kannahi M, Kowsalya M. J. Chem. Pharm. Res. 2013; 5: 46
- 2c Rajasekar S, Elango R. Curr. Botany 2011; 2: 27
- 2d Bloemberg GV, Lugtenberg BJ. J. Curr. Opin. Plant Biol. 2001; 4: 343
- 3a Jofre E, Lagares A, Mori G. FEMS Microbiol. Lett. 2004; 231: 267
- 3b Burdman S, Okon Y, Jurkevitch E. Crit. Rev. Microbiol. 2000; 26: 91
- 3c Egorenkova IV, Konnova SA, Sachuk VN, Ignatov VV. Plant Soil 2001; 231: 275
- 4a Weller DM. Annu. Rev. Phytopathol. 1988; 26: 379
- 4b Guo YB, Li J, Li L, Chen F, Wu W, Wang J, Wang H. Appl. Environ. Microbiol. 2009; 75: 6792
- 4c Bashan Y, de-Bashan LE. Adv. Agron. 2010; 108: 77
- 5a Bashan Y, de-Bashan LE. Appl. Environ. Microbiol. 2002; 68: 2637
- 5b Bashan Y, de-Bashan LE. Eur. J. Plant Pathol. 2002; 108: 821
- 5c Romero AM, Correa O, Moccia S, Rivas JG. J. Appl. Microbiol. 2003; 95: 832
- 6a Figueiredo MV. B, Seldin L, de Araujo FF, de Lima Ramos Mariano R In Plant Growth and Health Promoting Bacteria . Maheshwari DK. Springer; Berlin: 2011: 21-43
- 6b Ptacek SD, Gysegom P, Srinivasan M, Vanderleyden J. Appl. Environ. Microbiol. 2005; 71: 1803
- 7 Sigida EN, Fedonenko YP, Zdorovenko EL, Konnova SA, Shashkov AS, Ignatov VV, Knirel YA. Carbohydr. Res. 2013; 371: 40
- 8a Mandal PK, Misra AK. Bioorg. Chem. 2010; 38: 56
- 8b Mandal PK, Misra AK. Glycoconjugate J. 2008; 25: 713
- 8c Mandal PK, Misra AK. Tetrahedron 2008; 64: 8685
- 8d Agnihotri G, Mandal PK, Misra AK. Tetrahedron 2007; 63: 7240
- 8e Mandal PK, Misra AK. Synthesis 2007; 2660
- 8f Mandal PK, Branson TR, Hayes ED, Ross JF, Gavín JA, Daranas AH, Turnbull WB. Angew. Chem. Int. Ed. 2012; 51: 5143
- 9 Liptak A, Imre J, Nanasi P. Carbohydr. Res. 1981; 92: 154
- 10 Madhusudan SK, Agnihotri G, Negi DS, Misra AK. Carbohydr. Res. 2005; 340: 1373
- 11 Bouchra M, Calinaud P, Gelas J. Carbohydr. Res. 1995; 267: 227
- 12 Dinkelaar J, de Jong AR, Van Meer R, Somers M, Lodder G, Overkleeft HS, Codee JD. C, Van der Marel GA. J. Org. Chem. 2009; 74: 4982
- 13a Veeneman GH, van Leeuwen SH, van Boom JH. Tetrahedron Lett. 1990; 31: 1331
- 13b Konradsson P, Udodong UE, Fraser-Reid B. Tetrahedron Lett. 1990; 31: 4313
- 14 Bock K, Lundt I, Pedersen C. Tetrahedron Lett. 1973; 14: 1037
- 15 Paulsen H, Brenken M. Liebigs Ann. Chem. 1988; 649
- 16 Pearlman WM. Tetrahedron Lett. 1967; 8: 1663
- 17 Ichikawa Y, Matsukawa Y, Tamura M, Ohara F, Isobe M, Kotasuki H. Chem. Asian J. 2006; 1: 717
- 18 Jacquinet J.-C. Carbohydr. Res. 2004; 339: 349
- 19 Lönn H. Carbohydr. Res. 1985; 139: 105
- 20 Kumar R, Maulik PR, Misra AK. Glycoconjugate J. 2008; 25: 511
- 21 Vic G, Hasting JJ, Howarth OW, Crout DH. G. Tetrahedron: Asymmetry 1996; 7: 709
- 22 Kanie O, Crawley SC, Palcic MM, Hindsgaul O. Carbohydr. Res. 1993; 243: 139