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Synthesis 2011(17): 2761-2766  
DOI: 10.1055/s-0030-1260139
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

6-O-Amino-2-O-carboxymethyl Glucopyranoside as Novel Glycoaminoxy Acid Building Block for the Construction of Oligosaccharide Mimetics

Zhuo Songa, Xiao-Peng Hea,b, Guo-Rong Chen*a, Juan Xie*b
a Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, Shanghai 200237, P. R. of China
Fax: +86(21)64252758; e-Mail: mrs_guorongchen@ecust.edu.cn;
b PPSM, ENS Cachan, CNRS, 61 Ave President Wilson, 94230 Cachan, France
Fax: +33(1)47402454; e-Mail: joanne.xie@ens-cachan.fr;
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Publication History

Received 22 April 2011
Publication Date:
28 July 2011 (online)

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Abstract

The synthesis of diversely functionalized carbohydrate building blocks is of great interest towards the generation of new carbohydrate mimetics. Glycoaminoxy acids are recently developed glycoamino acid analogues with both an aminoxy and a carboxyl group connected to the sugar scaffold. These molecules could be readily used for the synthesis of various glycoconjugates through N-oxy amide or oxime bond, thus providing a potent tool for the design of novel functional carbohydrate mimetics. Here, the efficient synthesis of 2,6-functionalized pyranoid glycoaminoxy acid from commercially available methyl glucopyranoside is reported. The subsequent assembly of this glycoaminoxy acid building unit via N-acylation led successfully to the novel 2,6-linked oligosaccharide mimetics.

Key words

aminoxy acids - glycoaminoxy acids - oligosaccharide mimetics - carbohydrates - oligomers

    References

  • For reviews, see:
  • 1a Sears O. Wong CH. Angew. Chem. Int. Ed.  1999,  38:  2300 
    Search in Google Scholar
  • 1b Schweizer F. Angew. Chem. Int. Ed.  2002,  41:  230 
    Search in Google Scholar
  • 1c Gruner SAW. Locardi E. Lohof E. Kessler H. Chem. Rev.  2002,  102:  491 
    Search in Google Scholar
  • 1d Chakraborty TK. Ghosh S. Jayaprakash S. Curr. Med. Chem.  2002,  9:  421 
    Search in Google Scholar
  • 1e Gervay-Hague J. Weathers TM. J. Carbohydr. Chem.  2002,  7-9:  867 
    Search in Google Scholar
  • 1f Chakraborty TK. Srinivasu P. Tapadar S. Mohan BK. J. Chem. Sci.  2004,  116:  187 
    Search in Google Scholar
  • 1g Chakraborty TK. Srinivasu P. Tapadar S. Mohan BK. Bioconjugate J.  2005,  22:  83 
    Search in Google Scholar
  • 1h Risseeuw MDP. Overhand M. Fleet GWJ. Simone MI. Tetrahedron: Asymmetry  2007,  18:  2001 
    Search in Google Scholar
  • 1i Koester DC. Holkenbrink A. Werz DB. Synthesis  2010,  3217 
  • 2a Yang D. Ng F.-F. Li Z.-J. Wu Y.-D. Chan KWK. Wang D.-P. J. Am. Chem. Soc.  1996,  118:  9794 
    Search in Google Scholar
  • 2b Yang D. Qu J. Li B. Ng F.-F. Wang X.-C. Cheung K.-K. Wang D.-P. Wu Y.-D. J. Am. Chem. Soc.  1999,  121:  589 
    Search in Google Scholar
  • 2c Shin I. Lee M. Lee J. Jung M. Lee W. Yoon J. J. Org. Chem.  2000,  65:  7667 
    Search in Google Scholar
  • 2d Yang D. Li B. Ng F.-F. Yan Y.-L. Qu J. Wu Y.-D. J. Org. Chem.  2001,  66:  7303 
    Search in Google Scholar
  • 2e Chen F. Song K.-S. Wu Y.-D. Yang D. J. Am. Chem. Soc.  2008,  130:  743 
    Search in Google Scholar
  • 2f Li X. Wu Y.-D. Yang D. Acc. Chem. Res.  2008,  41:  1428 
    Search in Google Scholar
  • 2g Li X. Yang D. Chem. Commun.  2006,  3367 
  • 2h Yang D. Zhang D.-W. Hao Y. Wu Y.-D. Luo S.-W. Zhu N.-Y. Angew. Chem. Int. Ed.  2004,  43:  6719 
    Search in Google Scholar
  • 2i Yang D. Zhang X.-W. Zhang D.-W. Jiang Z.-F. Song K.-S. Zhang Y.-H. Zhu N.-Y. Weng L.-H. Chen M.-Q. J. Org. Chem.  2010,  75:  4796 
    Search in Google Scholar
  • 2j Zhang Y.-H. Song K. Zhu N.-Y. Yang D. Chem. Eur. J.  2010,  16:  577 
    Search in Google Scholar
  • 3 Malapelle A. Ramozzi R. Xie J. Synthesis  2009,  888 
    Thieme Connect
  • 4 Chandrasekhar S. Rao CL. Reddy MS. Sharma GD. Kiran MU. Naresh P. Chaitanya GK. Bhanuprakash K. Jagadeesh B. J. Org. Chem.  2008,  73:  9443 
    CrossrefSearch in Google Scholar
  • 5 Gong Y. Sun H. Xie J. Eur. J. Org. Chem.  2009,  6027 
  • 6a Rodriguez EC. Marcaurelle LA. Bertozzi CR. J. Org. Chem.  1998,  63:  7134 
    Search in Google Scholar
  • 6b Duléry V. Renaudet O. Philouze C. Dumy P. Carbohydr. Res.  2007,  342:  894 
    Search in Google Scholar
  • 6c Chen W. Xia C. Cai L. Wang PG. Bioorg. Med. Chem. Lett.  2010,  20:  3859 
    Search in Google Scholar
  • 7a Brask J. Jensen KJ. J. Pept. Sci.  2000,  6:  290 
    Search in Google Scholar
  • 7b Brask J. Jensen KJ. Bioorg. Med. Chem. Lett.  2001,  11:  697 
    Search in Google Scholar
  • 7c Tofteng AP. Hansen TH. Brask J. Nielsen J. Thulstrup PW. Jensen KJ. Org. Biomol. Chem.  2007,  5:  2225 
    Search in Google Scholar
  • 7d Jiménez-Castells C. de la Torre BG. Gutiérrez Gallego R. Andreu D. Bioorg. Med. Chem. Lett.  2007,  17:  5155 
    Search in Google Scholar
  • 8 Clo E. Blixt O. Jensen KJ. Eur. J. Org. Chem.  2010,  540 
  • 9 Tejler J. Salameth B. Leffler H. Nilsson UJ. Org. Biomol. Chem.  2009,  7:  3982 
    CrossrefSearch in Google Scholar
  • 10a Xie J. Eur. J. Org. Chem.  2002,  3411 
  • 10b Xie J. Carbohydr. Res.  2003,  338:  399 
    Search in Google Scholar
  • 10c Xie J. Durrat F. Valéry JM. J. Org. Chem.  2003,  68:  7896 
    Search in Google Scholar
  • 10d Durrat F. Xie J. Valéry JM. Tetrahedron Lett.  2004,  45:  1477 
    Search in Google Scholar
  • 10e Ménand M. Blais J.-C. Hamon L. Valéry J.-M. Xie J. J. Org. Chem.  2005,  70:  4423 
    Search in Google Scholar
  • 10f Ménand M. Blais J.-C. Valéry J.-M. Xie J. J. Org. Chem.  2006,  71:  3295 
    Search in Google Scholar
  • 10g Ayadi E. Czernecki S. Xie J. J. Chem. Soc., Chem. Commun.  1996,  347 
  • 11a Song S.-X. Zhang H.-L. Kim C.-K. Sheng L. He X.-P. Long Y.-T. Li J. Chen G.-R. Tetrahedron  2010,  66:  9974 
    Search in Google Scholar
  • 11b Yang JW. He X.-P. Li C. Gao L.-X. Sheng L. Xie J. Shi X.-X. Tang Y. Li J. Chen G.-R. Bioorg. Med. Chem. Lett.  2011,  21:  1092 
    Search in Google Scholar
  • 11c He X.-P. Wang X.-W. Jin X.-P. Zhou H. Shi X.-X. Chen G.-R. Long Y.-T. J. Am. Chem. Soc.  2011,  133:  3649 
    Search in Google Scholar
  • 12a Mereyala HB. Gurrala SR. Mohan SK. Tetrahedron  1999,  55:  11331 
    Search in Google Scholar
  • 12b He X.-P. Li C. Jin X.-P. Song Z. Zhang H.-L. Zhu C.-J. Shen Q. Zhang W. Shi X.-X. Tang Y. Li J. Chen G.-R. Xie J. New J. Chem.  2011,  35:  622 
    Search in Google Scholar