Concise Chemical Synthesis of the Tetrasaccharide Repeating Unit of the O-Antigen from Bovine Mastitis Isolate E. coli Serotype O174:H28

Abstract

A concise strategy for the chemical synthesis of the tetrasaccharide repeating unit of the O-antigen from E. coli O174:H28 is reported. Synthesis of the target structure is accomplished by sequential glycosylation of rationally protected monosaccharide synthons derived from commercially available sugars. Glycosylation reactions were achieved by the activation of the thioglycosides using N-iodosuccinimide in the presence of H₂SO₄–silica. The carboxylic acid moiety of the glucuronic acid unit was successfully installed by a late TEMPO-mediated oxidation of the primary hydroxy group. Phthalimido groups were successfully used as the precursors of the required acetamido functionalities for 1,2-trans-glycosylations.

Key words

bacterial O-antigen - acetamido sugars - H₂SO₄–silica

• Reference

• 1 Weintraub A. Carbohydr. Res. 2003; 338: 2539
• 2 Roy R. Drug Discovery Today: Technol. 2004; 1: 327
• 3 Doores KJ, Gamblin DP, Davis BG. Chem. Eur. J. 2006; 12: 656
• 4 Kuberan B, Linhardt RJ. Curr. Org. Chem. 2000; 4: 653
• 5 Duda KA, Fruth A, Holst O. Carbohydr. Res. 2013; 373: 18
• 6 Verma P, Mukhopadhyay B. Carbohydr. Res. 2011; 346: 2342
• 7 Balavoine G, Berteina S, Gref A, Fischer J.-C, Lubineau A. J. Carbohydr. Chem. 1995; 14: 1217
• 8 Pal KB, Mukhopadhyay B. Carbohydr. Res. 2014; 400: 9
• 9 Das R, Mahanti M, Mukhopadhyay B. Carbohydr. Res. 2014; 399: 15
• 10 Das R, Mukhopadhyay B. Carbohydr. Res. 2013; 376: 1
• 11 Pal KB, Mukhopadhyay B. Carbohydr. Res. 2013; 379: 26
• 12 Verma PR, Mukhopadhyay B. RSC Adv. 2013; 3: 201
• 13 Debenham SD, Toone EJ. Tetrahedron: Asymmetry 2000; 11: 385
• 14 Lee JC, Greemberg WA, Wong CH. Nat. Protoc. 2006; 1: 3143
• 15 Bertolini MJ, Glaudemans CP. J. Carbohydr. Res. 1970; 15: 263
• 16 Takeo K, Maki K, Wada Y, Kitamura S. Carbohydr. Res. 1993; 245: 81
• 17 Mukhopadhyay B, Kartha KP. R, Russell DA, Field RA. J. Org. Chem. 2004; 69: 7758
• 18 Gent PA, Gigg R. J. Chem. Soc., Perkin Trans. 1 1974; 1446
• 19 Kanie O, Crawley SC, Palcic MM, Hindsgaul O. Carbohydr. Res. 1993; 243: 139
• 20 Van den Bos LJ, Codee JD. C, van der Toorn JC, Boltje TJ, van Boom JH, Overkleeft HS, van der Marel GA. Org. Lett. 2004; 6: 2165
• 21 Zemplen G. Ber. Dtsch. Chem. Ges. 1926; 59: 1254
• 22 Perrin DD, Amarego WL, Perrin DR. Purification of Laboratory Chemicals . Pergamon; London: 1996
• 23 Mukhopadhyay B. Tetrahedron Lett. 2006; 47: 4337