Synthesis, Table of Contents Synthesis 2024; 56(03): 487-495DOI: 10.1055/s-0043-1763649 paper Convenient Synthesis of the Branched Hexasaccharide Repeating Unit of the Cell Wall O-Antigen of Escherichia coli O80 Strain Authors Samim Sahaji Anup Kumar Misra∗ Recommend Article Abstract Buy Article(opens in new window) All articles of this category(opens in new window) 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 Key wordscarbohydrates - glycosylation - glycoside - oligosaccharide - synthesis - Escherichia coli Full Text References 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 Supplementary Material Supplementary Material Supporting Information (PDF)