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Synthesis 2018; 50(21): 4270-4282
DOI: 10.1055/s-0037-1609719
paper
© Georg Thieme Verlag Stuttgart · New York

Zwitterionic Polysaccharides of Shigella sonnei: Synthetic Study toward a Ready-for-Oligomerization Building Block Made of Two Rare Amino Sugars

Hélène B. Pfister
a   Institut Pasteur, Unité de Chimie des Biomolécules, 28 rue du Dr Roux, 75724 Paris Cedex 15, France   Email: laurence.mulard@pasteur.fr
b   CNRS UMR3523, Institut Pasteur, 28 rue du Dr Roux, 75015 Paris, France
c   Université Paris Descartes Sorbonne Paris Cité, Institut Pasteur, 28 rue du Dr Roux, 75015 Paris, France
,
Julie Paoletti
a   Institut Pasteur, Unité de Chimie des Biomolécules, 28 rue du Dr Roux, 75724 Paris Cedex 15, France   Email: laurence.mulard@pasteur.fr
b   CNRS UMR3523, Institut Pasteur, 28 rue du Dr Roux, 75015 Paris, France
,
Ana Poveda
d   Molecular Recognition & Host-Pathogen Interactions Program, CIC bioGUNE, Bizkaia Technological Park, Bldg 801A, 48160 Derio, Spain
e   Ikerbasque, Basque Foundation for Science, Maria Lopez de Haro 3, 48013 Bilbao, Spain
,
Jesus Jimenez-Barbero
d   Molecular Recognition & Host-Pathogen Interactions Program, CIC bioGUNE, Bizkaia Technological Park, Bldg 801A, 48160 Derio, Spain
e   Ikerbasque, Basque Foundation for Science, Maria Lopez de Haro 3, 48013 Bilbao, Spain
,
Laurence A. Mulard*
a   Institut Pasteur, Unité de Chimie des Biomolécules, 28 rue du Dr Roux, 75724 Paris Cedex 15, France   Email: laurence.mulard@pasteur.fr
b   CNRS UMR3523, Institut Pasteur, 28 rue du Dr Roux, 75015 Paris, France
› Author AffiliationsThis work has received funding from the Institut Pasteur, the MENESR, France (ENS Cachan, PhD fellowship to H. P.) and the European Commission Seventh Framework Program (FP7/2007–2013) under Grant agreement No. 261472-STOPENTERICS, which included a fellowship to J.P.
Further Information

Publication History

Received: 22 February 2018

Accepted after revision: 09 April 2018

Publication Date:
05 October 2018 (online)

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Published as part of the Special Section on the 26th French–Japanese Symposium on Medicinal and Fine Chemistry.

Abstract

Shigellosis is an endemic diarrheal disease caused by Gram negative bacteria named Shigella. The most exposed polysaccharides of Shigella sonnei display a zwitterionic disaccharide repeating unit (AB) made of two rare amino sugars: [4)-α-l-AltpNAcA-(1→3)-β-d-FucpNAc4N-(1→]. An original synthesis of a ready-for-oligomerization AB disaccharide is reported. The targeted orthogonally protected disaccharide was synthesized from l-glucose and tetra-O-acetyl-β-d-glucosamine. The challenging introduction of the 4B-azido group masking the amino moiety of the AAT residue was performed at the disaccharide stage by a two-step procedure (triflation followed by nucleo­philic displacement with NaN3). A post-glycosylation oxidation strategy was employed to access the altruronate moiety.

Key words

amino sugars - glycosylation - oligosaccharide synthesis - shigellosis - vaccine

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1609719.
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  • References

  • 1 Current address: Section on Carbohydrates, LBC, NIDDK, NIH, 8 Center Drive, Bethesda, MD 20892-0815, USA.
  • 2 Current address: Minakem Dunkerque Production, 224 avenue de la Dordogne, 59640 Dunkerque, France.
  • 3 Troeger C. Forouzanfar M. Rao PC. Khalil I. Brown A. Reiner RC. Jr. Fullman N. Thompson RL. Abajobir A. Ahmed M. Alemayohu MA. Alvis-Guzman N. Amare AT. Antonio CA. Asayesh H. Avokpaho E. Awasthi A. Bacha U. Barac A. Betsue BD. Beyene AS. Boneya DJ. Malta DC. Dandona L. Dandona R. Dubey M. Eshrati B. Fitchett JR. A. Gebrehiwot TT. Hailu GB. Horino M. Hotez PJ. Jibat T. Jonas JB. Kasaeian A. Kissoon N. Kotloff K. Koyanagi A. Kumar GA. Rai RK. Lal A. El Razek HM. A. Mengistie MA. Moe C. Patton G. Platts-Mills JA. Qorbani M. Ram U. Roba HS. Sanabria J. Sartorius B. Sawhney M. Shigematsu M. Sreeramareddy C. Swaminathan S. Tedla BA. Jagiellonian RT.-M. Ukwaja K. Werdecker A. Widdowson M.-A. Yonemoto N. El Sayed Zaki M. Lim SS. Naghavi M. Vos T. Hay SI. Murray CJ. L. Mokdad AH. Lancet Infect. Dis. 2017; 17: 909
    CrossrefPubMed
  • 4 Liu J. Platts-Mills JA. Juma J. Kabir F. Nkeze J. Okoi C. Operario DJ. Uddin J. Ahmed S. Alonso PL. Antonio M. Becker SM. Blackwelder WC. Breiman RF. Faruque AS. G. Fields B. Gratz J. Haque R. Hossain A. Hossain MJ. Jarju S. Qamar F. Iqbal NT. Kwambana B. Mandomando I. McMurry TL. Ochieng C. Ochieng JB. Ochieng M. Onyango C. Panchalingam S. Kalam A. Aziz F. Qureshi S. Ramamurthy T. Roberts JH. Saha D. Sow SO. Stroup SE. Sur D. Tamboura B. Taniuchi M. Tennant SM. Toema D. Wu Y. Zaidi A. Nataro JP. Kotloff KL. Levine MM. Houpt ER. Lancet 2016; 388: 1291
    CrossrefPubMed
  • 5 Puzari M. Sharma M. Chetia P. J. Infect. Public Health 2018; 11: 451
    CrossrefPubMed
  • 6 Barry EM. Pasetti MF. Sztein MB. Fasano A. Kotloff KL. Levine MM. Nat. Rev. Gastroenterol. Hepatol. 2013; 10: 245
  • 7 Cohen D. Green MS. Block C. Slepon R. Ofek I. J. Clin. Microbiol. 1991; 29: 386
    CrossrefPubMed
  • 8 Passwell JH. Ashkenzi S. Banet-Levi Y. Ramon-Saraf R. Farzam N. Lerner-Geva L. Even-Nir H. Yerushalmi B. Chu C. Shiloach J. Robbins JB. Schneerson R. Vaccine 2010; 28: 2231
    CrossrefPubMed
  • 9 Phalipon A. Tanguy M. Grandjean C. Guerreiro C. Belot F. Cohen D. Sansonetti PJ. Mulard LA. J. Immunol. 2009; 182: 2241
    CrossrefPubMed
  • 10 Belot F. Guerreiro C. Baleux F. Mulard LA. Chem. Eur. J. 2005; 11: 1625
    CrossrefPubMed
    • 12a Boutet J. Blasco P. Guerreiro C. Thouron F. Dartevelle S. Nato F. Canada FJ. Arda A. Phalipon A. Jimenez-Barbero J. Mulard LA. Chem. Eur. J. 2016; 22: 10892
      CrossrefPubMed
    • 12b Hu Z. Bongat White AF. Mulard LA. Chem. Asian J. 2017; 12: 419
      CrossrefPubMed
  • 13 Kotloff KL. Winickoff JP. Ivanoff B. Clemens JD. Swerdlow DL. Sansonetti PJ. Adak GK. Levine MM. Bull. World Health Organ. 1999; 77: 651
    PubMed
  • 14 Holt KE. Baker S. Weill FX. Holmes EC. Kitchen A. Yu J. Sangal V. Brown DJ. Coia JE. Kim DW. Choi SY. Kim SH. da Silveira WD. Pickard DJ. Farrar JJ. Parkhill J. Dougan G. Thomson NR. Nat. Genet. 2012; 44: 1056
    CrossrefPubMed
  • 15 Thompson CN. Duy PT. Baker S. PLoS Negl. Trop. Dis. 2015; 9: e0003708
    CrossrefPubMed
  • 16 Caboni M. Pedron T. Rossi O. Goulding D. Pickard D. Citiulo F. MacLennan CA. Dougan G. Thomson NR. Saul A. Sansonetti PJ. Gerke C. PLoS Pathog. 2015; 11: e1004749
    CrossrefPubMed
  • 17 Kenne L. Lindberg B. Petersson K. Katzenellenbogen E. Romanowska E. Carbohydr. Res. 1980; 78: 119
    Crossref
  • 18 Pfister HB. Mulard LA. Org. Lett. 2014; 16: 4892
    CrossrefPubMed
    • 19a Christina AE. Ferrando VM. B. de Bordes F. Spruit WA. Overkleeft HS. Codee JD. C. van der Marel GA. Carbohydr. Res. 2012; 356: 282
      CrossrefPubMed
    • 19b Emmadi M. Kulkarni SS. Nat. Prod. Rep. 2014; 31: 870
      CrossrefPubMed
    • 20a Clark EL. Emmadi M. Krupp KL. Podilapu AR. Helble JD. Kulkarni SS. Dube DH. ACS Chem. Biol. 2016; 11: 3365
      CrossrefPubMed
    • 20b Podilapu AR. Kulkarni SS. Org. Lett. 2017; 19: 5466
      CrossrefPubMed
    • 21a Hullar TL. Siskin SB. J. Org. Chem. 1970; 35: 225
      CrossrefPubMed
    • 21b Hanessian S. Carbohydr. Res. 1966; 2: 86
      Crossref
    • 22a Hanessian S. Plessas NR. J. Org. Chem. 1969; 34: 1045
      Crossref
    • 22b Hou SJ. Kovac P. Carbohydr. Res. 2011; 346: 1394
      CrossrefPubMed
  • 23 Blatter G. Beau JM. Jacquinet JC. Carbohydr. Res. 1994; 260: 189
    CrossrefPubMed
  • 24 Medgyes A. Farkas E. Liptak A. Pozsgay V. Tetrahedron 1997; 53: 4159
    Crossref
  • 25 Qin ZH. Li H. Cai MS. Li ZJ. Carbohydr. Res. 2002; 337: 31
    CrossrefPubMed
    • 26a Osby JO. Martin MG. Ganem B. Tetrahedron Lett. 1984; 25: 2093
      Crossref
    • 26b Dasgupta S. Pramanik K. Mukhopadhyay B. Tetrahedron 2007; 63: 12310
      Crossref
    • 26c Shih HW. Chen KT. Cheng TJ. R. Wong CH. Cheng WC. Org. Lett. 2011; 13: 4600
      CrossrefPubMed
    • 27a Watanabe Y. Fujimoto T. Shinohara T. Ozaki S. J. Chem. Soc., Chem. Commun. 1991; 428
    • 27b Watanabe Y. Fujimoto T. Ozaki S. J. Chem. Soc., Chem. Commun. 1992; 681
  • 29 Wu XY. Cui LN. Lipinski T. Bundle DR. Chem. Eur. J. 2010; 16: 3476
    CrossrefPubMed
  • 30 Pirrung MC. Shuey SW. Lever DC. Fallon L. Bioorg. Med. Chem. Lett. 1994; 4: 1345
    Crossref
  • 31 Boutet J. Guerreiro C. Mulard LA. J. Org. Chem. 2009; 74: 2651
    CrossrefPubMed
    • 32a Braverman S. Cherkinsky M. Kedrova L. Reiselman A. Tetrahedron Lett. 1999; 40: 3235
      Crossref
    • 32b Nishikawa T. Urabe D. Tomita M. Tsujimoto T. Iwabuchi T. Isobe M. Org. Lett. 2006; 8: 3263
      CrossrefPubMed
    • 33a Werz DB. Seeberger PH. Angew. Chem. Int. Ed. 2005; 44: 6315
      CrossrefPubMed
    • 33b Cai Y. Ling CC. Bundle DR. J. Org. Chem. 2009; 74: 580
      CrossrefPubMed
    • 33c Emmadi M. Kulkarni SS. Org. Biomol. Chem. 2013; 11: 3098
      CrossrefPubMed
    • 34a Bassily RW. Elsokkary RI. Silwanis BA. Nematalla AS. Nashed MA. Carbohydr. Res. 1993; 239: 197
      CrossrefPubMed
    • 34b Oberli MA. Bindschadler P. Werz DB. Seeberger PH. Org. Lett. 2008; 10: 905
      CrossrefPubMed
  • 35 Shrestha AR. Hari Y. Yahara A. Osawa T. Obika S. J. Org. Chem. 2011; 76: 9891
    CrossrefPubMed
  • 36 Emmadi M. Kulkarni SS. Nat. Protoc. 2013; 8: 1870
    CrossrefPubMed
  • 37 Seeberger PH. Pereira CL. Govindan S. Beilstein J. Org. Chem. 2017; 13: 164
    CrossrefPubMed