Synthesis 2021; 53(19): 3613-3620
DOI: 10.1055/s-0037-1610777
paper

Synthesis of Pentasaccharide Repeating Unit Corresponding to the Cell Wall O-Polysaccharide of Salmonella enterica O55 Strain Containing a Rare Sugar 3-Acetamido-3-deoxy-d-fucose

Arin Gucchait
,
Monalisa Kundu
,
Anup Kumar Misra∗
A.G. and M.K. thank Council of Scientific and Industrial Research, New Delhi, India (CSIR) for providing senior research fellowships. This work was supported by Science and Engineering Research Board (SERB), New Delhi (Project No. CRG/2019/000352 dated 23.01.2020) (A.K.M.).
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Abstract

A pentasaccharide repeating unit corresponding to the cell wall O-antigen of Salmonella enterica O55 containing a rare sugar, 3-acetamido-3-deoxy-d-fucose has been synthesized as its p-methoxyphenyl glycoside using a sequential stereoselective glycosylation strategy. A suitably functionalized 3-azido-3-deoxy-d-fucose thioglycoside derivative was prepared in very good yield and used in the stereoselective glycosylation reaction. Functionalized monosaccharide intermediates were prepared judiciously and stereoselectively assembled to get the desired pentasaccharide derivative in excellent yield.

Key words

pentasaccharide - glycosylation - 3-acetamido-3-deoxy-d-fucose - Salmonella enterica - stereoselective

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610777. Copies of 1D and 2D NMR spectra of compounds 1 and 8–17 are provided.
  • Supporting Information


Publication History

Received: 24 April 2021

Accepted after revision: 31 May 2021

Article published online:
24 June 2021

© 2021. Thieme. All rights reserved

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  • References

    • 1a Mandeville KL, Krabshuis J, Ladep NG, Mulder CJ. J, Quigley EM. M, Khan SA. World J. Gastroenterol. 2009; 15: 2839
      CrossrefPubMed
    • 1b Milivojevic V, Milosavljevic T. Curr. Treat. Options Gastroenterol. 2020; 18: 148
      CrossrefPubMed
    • 1c Dumic I, Nordin T, Jecmenica M, Lalosevic MS, Milosavljevic T, Milovanovic T. Can. J. Gastroenterol. Hepatol. 2019; 2019: 6757524 , DOI: 10.1155/2019/6757524
      CrossrefPubMed
    • 2a Fletcher SM, Mclaws M.-L, Ellis JT. J. Public Health Res. 2013; 2: 42
      PubMed
    • 2b Williams J, Roberts S, Ali F, Cheung W, Cohen D, Demery G, Edwards A, Greer M, Hellier M, Hutchings H, Ip B, Longo M, Russell I, Snooks H, Williams J. Gut 2007; 56 (Suppl. 01) : 1
      PubMed
    • 2c Guerrant RL, Hughes JM, Lima NL, Crane J. Rev. Infect. Dis. 1990; 12: S41
      CrossrefPubMed
    • 3a Oloruntoba EO, Folarin TB, Idowu-Ayede A. Afr. Health Sci. 2014; 14: 1001
    • 3b Huttly SR, Morris SS, Pisani V. Bull. W. H. O. 1997; 75: 163
      CrossrefPubMed
    • 3c Florez ID, Niño-Serna LF, Beltrá-Arroyave CP. Curr. Infect. Dis. Rep. 2020; 22: 4 DOI: 10.1007/s11908-020-0713-6.
      CrossrefPubMed
    • 5a Beatty ME, Adcock PM, Smith SW, Quinlan K, Kamimoto LA, Rowe SY, Scott K, Conover C, Varchmin T, Bopp CA, Greene KD, Bibb B, Slutsker L, Mintz ED. Clin. Infect. Dis. 2006; 42: 329
      CrossrefPubMed
    • 5b Gomes TA. T, Elias WP, Scaletsky IC. A, Guth BE. C, Rodrigues JF, Piazza RM. F, Ferreira LC. S, Martinez MB. Braz. J. Microbiol. 2016; 47: 3
      CrossrefPubMed
  • 6 Baker S, The HC. Curr. Opin. Infect. Dis. 2018; 31: 449
    CrossrefPubMed
  • 7 Davies HG, Bowman C, Luby SP. J. Infect. 2017; 74 (Suppl. 01) : S66
    CrossrefPubMed
  • 8 Hamilton AL, Kamm MA, Ng SC, Morrison M. Clin. Microbiol. Rev. 2018; 31: e00085 DOI: 10.1128/CMR.00085-17.
    CrossrefPubMed
    • 9a Aljoudi AS, Al-Mazam A, Choudhry AJ. J. Family Community Med. 2010; 17: 29
      CrossrefPubMed
    • 9b Lu X, Zeng M, Xu J, Zhou H, Gu B, Li Z, Jin H, Wang X, Zhang W, Hu Y, Xiao W, Zhu B, Xu X, Kan B. EbioMedicine 2019; 42: 133
      CrossrefPubMed
    • 11a Stoycheva MV, Murdjeva MA. Folia Med. (Sofia, Bulg.) 2006; 48: 5
    • 11b Ray KA, Warnick LD, Mitchell RM, Kaneene JB, Ruegg PL, Wells SJ, Fossler CP, Halberd LW, May K. J. Dairy Sci. 2006; 89: 2038
      CrossrefPubMed
    • 11c Mu H, Bai H, Sun F, Liu Y, Lu C, Qiu Y, Chen P, Yang Y, Kong L, Duan J. Nat. Commun. 2019; 10: 4039
      CrossrefPubMed
    • 11d Hirose K, Tamura K, Sagara H, Watanabe H. Antimicrob. Agents Chemother. 2001; 45: 956
      CrossrefPubMed
    • 12a Jajere SM. Vet. World 2019; 12: 504
      CrossrefPubMed
    • 12b Eng S.-K, Pusparajah P, Ab Mutalib N.-S, Ser H.-L, Chan K.-G, Lee L.-H. Front. Life Sci. 2015; 8: 284
      Crossref
    • 13a Fair RJ, Tor Y. Perspect. Med. Chem. 2014; 6: 25
    • 13b Appelbaum PC. J. Antimicrob. Chemother. 2012; 67: 2062
      CrossrefPubMed
    • 13c Sipahi OR. Expert Rev. Anti-Infect. Ther. 2008; 6: 523
      CrossrefPubMed
    • 14a Moxon ER, Kroll JS. Curr. Top. Microbiol. Immunol. 1990; 150: 65
      PubMed
    • 14b Taylor CM, Roberts IS. Contrib. Microbiol. 2005; 12: 55
      PubMed
  • 15 Liu B, Perepelov AV, Svensson MV, Shevelev SD, Guo D, Senchenkova SN, Shashkov AS, Weintraub A, Feng L, Widmalm G, Knirel YA, Wang L. Glycobiology 2010; 20: 679
    CrossrefPubMed
  • 16 Gilchrist SA. N, Nanni A, Levine O. Am. J. Public Health 2012; 102: 596
    CrossrefPubMed
    • 17a Thindwa D, Quesada MG, Liu Y, Bennett J, Cohen C, Knoll MD, von Gottberg A, Hayford K, Flasche S. Vaccine 2020; 38: 5398
      CrossrefPubMed
    • 17b Nichol KL. Vaccine 1999; 17: S91
      CrossrefPubMed
    • 19a Gucchait A, Shit P, Misra AK. Tetrahedron 2020; 76: 131412
      Crossref
    • 19b Dhara D, Baliban SM, Huo CX, Rashidijahanabad Z, Sears KT, Nick ST, Misra AK, Tennant SM, Huang X. Chem. Eur. J. 2020; 26: 15953
      CrossrefPubMed
    • 19c Huo C.-X, Dhara D, Baliban SM, Nick ST, Tan Z, Simon S, Misra AK, Huang X. Chem. Commun. 2019; 55: 4519
      CrossrefPubMed
    • 19d Bhaumik I, Misra AK. ChemistrySelect 2017; 2: 3065
      Crossref
    • 19e Bhaumik I, Misra AK. ChemistrySelect 2017; 2: 937
      Crossref
    • 19f Dhara D, Misra AK. ChemistryOpen 2015; 4: 768
      CrossrefPubMed
    • 19g Dhara D, Mandal PK, Misra AK. Tetrahedron: Asymmetry 2014; 25: 263
      Crossref
    • 19h Ghosh T, Santra A, Misra AK. Tetrahedron: Asymmetry 2013; 24: 606
      Crossref
    • 19i Sau A, Panchadhayee R, Ghosh D, Misra AK. Carbohydr. Res. 2012; 352: 18
      CrossrefPubMed
  • 20 Nicolaou KC, Bockovich NJ, Carcanague DR, Hummel CW, Even LF. J. Am. Chem. Soc. 1992; 114: 8701
    CrossrefPubMed
  • 21 Kalikanda J, Li Z. J. Org. Chem. 2011; 76: 5207
    CrossrefPubMed
  • 22 Hsu Y, Lu X.-A, Zulueta ML, Tsai C.-M, Lin K.-I, Hung S.-C, Wong C.-H. J. Am. Chem. Soc. 2012; 134: 4549
    CrossrefPubMed
  • 23 Huang T.-Y, Zulueta MM. L, Hung S.-C. Org. Biomol. Chem. 2014; 12: 376
    CrossrefPubMed
    • 24a Mukherjee C, Misra AK. Synthesis 2007; 683
    • 24b Manna T, Gucchait A, Misra AK. Beilstein J. Org. Chem. 2020; 16: 106
      CrossrefPubMed
    • 24c Shit P, Misra AK. Glycoconjugate J. 2020; 37: 647
      CrossrefPubMed
    • 24d Kundu M, Gucchait A, Misra AK. Tetrahedron 2020; 76: 130952
      Crossref
    • 24e Manna T, Misra AK. Carbohydr. Res. 2021; 502: 108294
      CrossrefPubMed
    • 24f Kundu M, Misra AK. Carbohydr. Res. 2019; 486: 107830
      CrossrefPubMed
    • 24g Shit P, Gucchait A, Misra AK. Tetrahedron 2019; 75: 130697
      Crossref
  • 25 Chakraborti AK, Gulhane R. Chem. Commun. 2003; 1896
    PubMed
    • 26a Khatik GL, Sharma G, Kumar R, Chakraborti AK. Tetrahedron 2007; 63: 1200
      Crossref
    • 26b Kumar D, Kommi DN, Chebolu R, Garg SK, Kumar R, Chakraborti AK. RSC Adv. 2013; 3: 91
      Crossref
    • 26c Kumar D, Sonawane M, Pujala B, Jain VK, Bhagat S, Chakraborti AK. Green Chem. 2013; 15: 2872
      Crossref
    • 26d Rudrawar S, Besra RC, Chakraborti AK. Synthesis 2006; 2767
    • 26e Kumar R, Kumar D, Chakraborti AK. Synthesis 2007; 299
    • 26f Chakraborti AK, Sunay V, Chankeshwara SV. Org. Biomol. Chem. 2006; 4: 2769
      CrossrefPubMed
    • 26g Agarwal A, Rani S, Vankar YD. J. Org. Chem. 2004; 69: 6137
      CrossrefPubMed
    • 26h Misra AK, Tiwari P, Madhusudan SK. Carbohydr. Res. 2005; 340: 325
      CrossrefPubMed
    • 26i Misra AK, Tiwari P, Agnihotri G. Synthesis 2005; 260
    • 26j Khan AT, Choudhury LH, Ghosh S. J. Mol. Catal. A: Chem. 2006; 255: 230
      Crossref
    • 26k Ansari MI, Hussain MK, Yadav N, Gupta PK, Hajela K. Tetrahedron Lett. 2012; 53: 2063
      Crossref
    • 27a Das R, Mukhopadhyay B. ChemistryOpen 2016; 5: 401
      CrossrefPubMed
    • 27b Lian G, Zhang X, Yu B. Carbohydr. Res. 2015; 403: 13
      CrossrefPubMed
    • 27c Codée JD. C, Litjens RE. J. N, van den Bos LJ, Overkleeft HS, van der Marel GA. Chem. Soc. Rev. 2005; 34: 769
      CrossrefPubMed
  • 28 Adak A, Mukhopadhyay B. Carbohydr. Res. 2019; 476: 1
    CrossrefPubMed
  • 29 Kiyoi T, Nakai Y, Kondo H, Ishida H, Kiso M, Hasegawa A. Bioorg. Med. Chem. 1996; 4: 1167
    CrossrefPubMed
  • 30 Brimacombe JS. Methods Carbohydr. Chem. 1972; 6: 376
  • 31 Wuts PG. M. In Handbook of Reagents for Organic Synthesis: Reagents for Glycoside, Nucleotide, and Peptide Synthesis. Crich D. Wiley; Chichester: 2005: 425
    Google Scholar
  • 32 Dong H, Rahm M, Thota N, Deng L, Brinck T, Ramström O. Org. Biomol. Chem. 2013; 11: 648
    CrossrefPubMed
  • 33 Augé C, David S, Veyrières A. J. Chem. Soc., Chem. Commun. 1976; 375
  • 34 Dhakal B, Bohé L, Crich D. J. Org. Chem. 2017; 82: 9263
    CrossrefPubMed
  • 35 Lloyd D, Bylsma M, Bright DK, Chen X, Bennett CS. J. Org. Chem. 2017; 82: 3926
    CrossrefPubMed
  • 36 Lee H.-H, Schwartz DA, Harris JF, Carver JP, Krepinsky JJ. Can. J. Chem. 1986; 64: 1912
    Crossref
  • 37 Shangguan N, Katukojvala S, Greenberg R, Williams LJ. J. Am. Chem. Soc. 2003; 125: 7754
    CrossrefPubMed
  • 38 Pearlman WM. Tetrahedron Lett. 1967; 8: 1663
    Crossref