Convenient Synthesis of the Branched Hexasaccharide Repeating Unit of the Cell Wall O-Antigen of Escherichia coli O80 Strain

Abstract

Chemical synthesis of a branched hexasaccharide corresponding to the cell wall O-antigen of Escherichia coli (E. coli) O80 strain has been achieved in very good yield with satisfactory stereochemical outcome around the glycosidic linkages by applying a regio- and stereoselective [4+2] block glycosylation strategy. The tetrasaccharide diol derivative was synthesized from suitably functionalized monosaccharide intermediates using sequential stereoselective glycosylations and the disaccharide thioglycoside donor was obtained applying a regio- and stereoselective orthogonal armed-disarmed glycosylation strategy using protected thioglycoside derivatives. A late-stage TEMPO and bis(acetoxy)iodobenzene (BAIB) mediated regioselective oxidation of the primary hydroxyl group of the protected hexasaccharide derivative to the carboxylic acid was achieved leaving secondary hydroxyl groups unaffected.

Key words

carbohydrates - glycosylation - glycoside - oligosaccharide - synthesis - Escherichia coli

Publication History

Received: 11 October 2023

Accepted after revision: 16 November 2023

Article published online:
11 December 2023

• References

• 1 Kaper JB, Nataro JP, Mobley HL. T. Nat. Rev. Microbiol. 2004; 2: 123
• 2a Stecher B, Hardt WD. Trends Microbiol. 2008; 16: 107
• 2b Foster JW. Nat. Rev. Microbiol. 2004; 2: 898
• 3 Nataro JP, Kaper JB. Clin. Microbiol. Rev. 1998; 11: 142
• 4 Johnson JR, Gajewski A, Lesse AJ, Russo TA. J. Clin. Microbiol. 2003; 41: 5798
• 5 Liu B, Furevi A, Perepelov AV, Guo X, Cao H, Wang Q, Reeves PR, Knirel YA, Wang L, Widmalm G. FEMS Microbiol. Rev. 2020; 44: 655
• 6a Lerouge I, Vanderleyden J. FEMS Microbiol. Rev. 2002; 26: 17
• 6b Sampath VP. Agric. Nat. Res. 2018; 52: 115
• 7 Iguchi A, Iyoda S, Seto K, Morita-Ishihara T, Scheutz F, Ohnishi M. J. Clin. Microbiol. 2015; 53: 2427
• 8a Nikaido H. Annu. Rev. Biochem. 2009; 78: 119
• 8b Terreni M, Taccani M, Pregnolato M. Molecules 2021; 26: 2671
• 9a Rohokale R, Guo Z. ACS Infect. Dis. 2023; 9: 178
• 9b Mettu R, Chen C.-Y, Wu C.-Y. J. Biomed. Sci. 2020; 27: 9
• 10 Soysal N, Mariani-Kurkdjian P, Smail Y, Liguori S, Gouali M, Loukiadis E, Fach P, Bruyand M, Blanco J, Bidet P, Bonacorsi S. Emerging Infect. Dis. 2016; 22: 1604
• 11 Senchenkova SN, Guo X, Filatov AV, Perepelov AV, Liu B, Shashkov AS, Knirel YA. Carbohydr. Res. 2016; 432: 83
• 12 Borbás A, Szabó ZB, Szilágyi L, Bényei A, Lipták A. Tetrahedron 2002; 58: 5723
• 13 Andersen SM, Ling C.-C, Zhang P, Townson K, Willison HJ, Bundle DR. Org. Biomol. Chem. 2004; 2: 1199
• 14 Misra AK, Roy N. J. Carbohydr. Chem. 1998; 17: 1047
• 15 van der Ven JG, Kerékgyártó J, Kamerling JP, Lipták A, Vliegenthart JF. Carbohydr. Res. 1994; 264: 45
• 16 Mandal PK, Misra AK. Glycoconj. J. 2008; 25: 713
• 17 Freser-Reid B, López JC. Top. Curr. Chem. 2011; 301: 1
• 18 Jana SK, Sahaji S, Shit P, Misra AK. Synthesis 2023; 55: 1553
• 19 Nyffeler PT, Liang C.-H, Koeller KM, Wong C.-H. J. Am. Chem. Soc. 2002; 124: 10773
• 20 van den Bos LJ, Litjens R, van den Berg R, Overkleeft HS, van der Marel GA. Org. Lett. 2005; 7: 2007
• 21 Tamborrini M, Werz DB, Frey J, Pluschke G, Seeberger PH. Angew. Chem. Int. Ed. 2006; 45: 6581
• 22 Norberg T, Ritzen H. Glycoconj. J. 1986; 3: 135
• 23a Veeneman GH, van Leeuwen SH, van Boom JH. Tetrahedron Lett. 1990; 31: 1331
• 23b Konradsson P, Udodong UE, Fraser-Reid B. Tetrahedron Lett. 1990; 31: 4313
• 24 Lee H.-H, Schwartz DA, Harris JF, Carver JP, Krepinsky JJ. Can. J. Chem. 1986; 64: 1912
• 25 Lewbart ML, Schneider JJ. J. Org. Chem. 1969; 34: 3505
• 26 Smith M, Rammler DH, Goldberg IH, Khorana HG. J. Am. Chem. Soc. 1962; 84: 430
• 27a Mandal PK, Misra AK. Tetrahedron 2008; 64: 8685
• 27b Dhara D, Kar RK, Bhunia A, Misra AK. Eur. J. Org. Chem. 2014; 4577
• 28 Shangguan N, Katukojvala S, Greenberg R, Williams LJ. J. Am. Chem. Soc. 2003; 125: 7754
• 29 Pearlman WM. Tetrahedron Lett. 1967; 8: 1663