Concise Synthesis of the Repeating Units of the Cell Wall Lipopolysaccharide of Azospirillum brasilense SR80

Pintu Kumar Mandal; Debashis Dhara; Anup Kumar Misra

doi:10.1055/s-0033-1341256

Synthesis, Inhaltsverzeichnis

Synthesis 2014; 46(14): 1947-1953
DOI: 10.1055/s-0033-1341256

paper

Concise Synthesis of the Repeating Units of the Cell Wall Lipopolysaccharide of Azospirillum brasilense SR80

Pintu Kumar Mandal*

^aMedicinal and Process Chemistry Division, CSIR-Central Drug Research Institute, BS-10/1, Sector 10, Jankipuram Extension, Sitapur Road, Lucknow-226 031, India Fax: +91(522)2623405 eMail: pintuchem06@gmail.com

,

Debashis Dhara

^bBose Institute, Division of Molecular Medicine, P-1/12, C.I.T. Scheme VII-M, Kolkata-700054 India

,

Anup Kumar Misra

^bBose Institute, Division of Molecular Medicine, P-1/12, C.I.T. Scheme VII-M, Kolkata-700054 India

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

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.

Key words

Azospirillum brasilense - tetrasaccharide - trisaccharide - lipopolysaccharide - plant-growth-promoting bacteria

Volltext

Referenzen

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