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Synthesis
DOI: 10.1055/a-2642-4514
DOI: 10.1055/a-2642-4514
Paper
Straightforward Synthesis of Functionalized l-Quinovosamine Thioglycoside Derivatives and Their Direct Use in the Synthesis of the Tetrasaccharide Corresponding to the Cell Wall of Escherichia coli O98
Abstract
Synthesis of functionalized l-quinovosamine thioglycoside was achieved in very good yield using simple functional group manipulation of l-rhamnose. l-quinovosamine thioglycoside derivatives have been successfully used in the total synthesis of the tetrasaccharide repeating unit of the cell wall O-antigen of Escherichia coli O98 strain. Two units of l-quinovosamine thioglycoside were stereoselectively glycosylated during the synthesis of the tetrasaccharide. In addition, direct conversion of azido groups into acetamido functionality and TEMPO-mediated (diacetoxyiodo)benzene (DAIB) oxidation of a primary hydroxyl group to a carboxylic group are noteworthy features of the synthetic strategy.
Publication History
Received: 29 April 2025
Accepted after revision: 24 June 2025
Article published online:
08 August 2025
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References
- 1 Mokomane M, Kasvosve I, de Melo E, Pernica JM, Goldfarb DM. Ther Adv Infect Dis 2017; 5: 29-43
- 2 Waterer G, Wunderink R. Respirology 2009; 14: 651-655
- 3 Barber AE, Norton JP, Spivak AM, Mulvey MA. Clin Infect Dis 2013; 57: 719-724
- 4 Khan HA, Ahmad A, Mehboob R. Asian Pac J Trop Biomed 2015; 5: 509-514
- 5 Mancuso G, Midiri A, Gerace E, Biondo C. Pathogens 2021; 10: 1310
- 6 Bharadwaj A, Rastogi A, Pandey S, Gupta S, Sohal JS. Biomed Res Int 2022; 2022: 5419874
- 7 Hudak JE, Bertozzi CR. Chem Biol 2014; 21: 16-37
- 8a Valverde P, Ardá A, Reichardt N-C, Jiménez-Barbero J, Gimeno A. Med Chem Commun 2019; 10: 1678-1691
- 8b Astronomo RD, Burton DR. Nat Rev Drug Discovery 2010; 9: 308-324
- 9a Micoli F, Costantino P, Adamo R. FEMS Microbiol Rev 2018; 42: 388-423
- 9b Rohokale R, Guo Z. ACS Infect Dis 2023; 9: 178-212
- 9c Khatun F, Stephenson RJ, Toth I. Chem Eur J 2016; 23: 4233-4254
- 9d Sorieul C, Dolce M, Romano MR, Codée JCD, Adamo R. Expert Rev Vaccine 2023; 22: 1055-1078
- 9e Kong L, Vijayakrishnan B, Kowarik M. et al. Nat Chem 2016; 8: 242-249
- 10a Crawford CJ, Seeberger PH. Chem Soc Rev 2023; 52: 7773-7801
- 10b Kinnaert C, Daugaard M, Nami F, Clausen MH. Chem Rev 2017; 117: 11337-11405
- 10c Seeberger PH, Werz DB. Nature 2007; 446: 1046-1051
- 10d Li B-H, Ye X-S. Curr Opin Chem Biol 2020; 58: 20-27
- 11a Shit P, Misra AK. Tetrahedron 2022; 122: 132948
- 11b Manna T, Misra AK. Carbohydr Res 2022; 521: 108668
- 11c Sahaji S, Misra AK. Synthesis 2024; 56: 487-495
- 11d Jana SK, Shit P, Misra AK. Synthesis 2023; 55: 773-778
- 11e Kundu M, Gucchait A, Misra AK. Tetrahedron 2021; 91: 132245
- 12 Marsden BJ, Bundle DR, Perry MB. Biochem Cell Biol 1994; 72: 163-168
- 13a Kaper JB, Nataro JP, Mobley HLT. Nat Rev Microbiol 2004; 2: 123-140
- 13b Nguyen Y, Sperandio V. Front Cell Infect Microbiol 2012; 2: 90
- 14 Laura B, Federica G, Francesca V. et al. Acta Biomed 2018; 89: 153-157
- 15a Behera A, Kulkarni SS. Molecules 2018; 23: 1997
- 15b Luong P, Ghosh A, Moulton KD, Kulkarni SS, Dube DH. ACS Infect Dis 2022; 8: 889-900
- 15c Sanapala SR, Kulkarni SS. J Am Chem Soc 2016; 138: 4938-4947
- 15d Chaudhury A, Ghosh R. Org Biomol Chem 2017; 15: 1444-1452
- 15e Sangwan R, Khanam A, Mandal PK. Eur J Org Chem 2020; 2020: 5949-5977
- 15f Lawton BT, Szarek WA, Jones JKN. Carbohydr Res 1970; 15: 397-402
- 15g Zhou Y, Liao K-S, Li S-T, Wu C-Y. Front Chem 2022; 10: 865026
- 15h Emmadi M, Kulkarni SS. Org Biomol Chem 2013; 11: 3098-3102
- 15i Emmadi M, Kulkarni SS. Nat Prod Rep 2014; 31: 870-879
- 15j Yang J, Xie D, Ma X. Molecules 2023; 28: 4724
- 16a Bhaumik I, Misra AK. ChemistrySelect 2017; 2: 3065-3067
- 16b Ghosh A, Kulkarni SS. Org Lett 2023; 25: 7242-7246
- 17 Ghoneim AA. Chem Cent J 2011; 5: 7
- 18 Cumpstey I, Fairbanks AJ, Redgrave AL. Tetrahedron 2004; 60: 9061-9074
- 19 Lipták A, Imre J, Nanási P. Carbohydr Res 1981; 92: 154-156
- 20 Madhusudan SK, Agnihotri G, Negi DS, Misra AK. Carbohydr Res 2005; 340: 1373-1377
- 21 Kováč P. Carbohydr Res 1993; 245: 219-231
- 22 Paul A, Rai D, Pradhan K, Balhara P, Mishra AK, Kulkarni SS. Org Lett 2023; 25: 6413-6418
- 23 Mukherjee C, Misra AK. Tetrahedron: Asymmetry 2008; 19: 2746-2751
- 24 Kihlberg JO, Leigh DA, Bundle DR. J Org Chem 1990; 55: 2860-2863
- 25 Shangguan N, Katukojvala S, Greenberg R, Williams LJ. J Am Chem Soc 2003; 125: 7754-7755
- 26 van den Bos LJ, Litjens R, van den Berg R, Overkleeft HS, van der Marel GA. Org Lett 2005; 7: 2007-2010
- 27 Brimacombe JS. Methods Carbohydr Chem 1972; 6: 376-378
- 28 Debenham SD, Toone EJ. Tetrahedron: Asymmetry 2000; 11: 385-387
- 29 Veeneman GH, van Leeuwen SH, van Boom JH. Tetrahedron Lett 1990; 31: 1331
- 30 Konradsson P, Udodong UE, Fraser-Reid B. Tetrahedron Lett 1990; 31: 4313-4316
- 31 Demchenko AV. ed Handbook of Chemical Glycosylation. Weinheim: Wiley-VCH; 2008
- 32 Lee H-H, Schwartz DA, Harris JF, Carver JP, Krepinsky JJ. Can J Chem 1986; 64: 1912-1918
- 33 Pearlman WM. Tetrahedron Lett 1967; 8: 1663-1664
- 34 Misra AK, Ding Y, Lowe JB, Hindsgaul O. Bioorg Med Chem Lett 2000; 10: 1505-1509
- 35 Chida N, Ohtsuka M, Nakazawa K, Ogawa S. J Org Chem 1991; 56: 2976-2983