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Synthesis 2009(6): 888-890  
DOI: 10.1055/s-0028-1083372
SHORTPAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Glycoaminoxy Acids as Novel Sugar Building Blocks

Adeline Malapelle, Romain Ramozzi, Juan Xie*
PPSM, ENS Cachan, Institut d’Alembert, CNRS, Universud, 61 av. Président Wilson, 94230 Cachan, France
Fax: +33(1)47402454; e-Mail: joanne.xie@ens-cachan.fr;
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Publikationsverlauf

Received 13 November 2008
Publikationsdatum:
11. Februar 2009 (online)

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Abstract

Glycoaminoxy acids, a new class of sugar building blocks bearing both aminoxy and carboxylic acid functional groups on the sugar ring, have been efficiently synthesized from α-C-allyl glycosides. These compounds can be easily used for the synthesis of an N-oxy-amide-linked disaccharide and glycosyl amino acid mimetics.

Key words

glycoaminoxy acids - glycopeptides - glycomimetics - glycosides - oligosaccharides

    References

  • For reviews of sugar amino acids, see:
  • 1a Schweizer F. Angew. Chem. Int. Ed.  2002,  41:  231 
    Google Scholar
  • 1b Gervay-Hague J. Weathers TM. J. Carbohydr. Chem.  2002,  7-9:  867 
    Google Scholar
  • 1c Gruner SAW. Locardi E. Lohof E. Kessler H. Chem. Rev.  2002,  102:  491 
    Google Scholar
  • 1d Chakraborty TK. Ghosh S. Jayaprakash S. Curr. Med. Chem.  2002,  9:  421 
    Google Scholar
  • 1e Chakraborty TK. Srinivasu P. Tapadar S. Mohan BK. J. Chem. Sci.  2004,  116:  187 
    Google Scholar
  • 2a Yang D. Ng F.-F. Li Z.-J. Wu Y.-D. Chan KWK. Wang D.-P. J. Am. Chem. Soc.  1996,  118:  9794 
    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 
    Google Scholar
  • 2c Shin I. Lee M. Lee J. Jung M. Lee W. Yoon J. J. Org. Chem.  2000,  65:  7667 
    Google Scholar
  • 2d Yang D. Li B. Ng F.-F. Yan Y.-L. Qu J. Wu Y.-D. J. Org. Chem.  2001,  66:  7303 
    Google Scholar
  • 2e Chen F. Song K.-S. Wu Y.-D. Yang D. J. Am. Chem. Soc.  2008,  130:  743 
    Google Scholar
  • 2f Li X. Wu Y.-D. Yang D. Acc. Chem. Res.  2008,  41:  1428 
    Google Scholar
  • 3a Li X. Yang D. Chem. Commun.  2006,  3367 
    Google Scholar
  • 3b Yang D. Zhang D.-W. Hao Y. Wu Y.-D. Luo S.-W. Zhu N.-Y. Angew. Chem. Int. Ed.  2004,  43:  6719 
    Google Scholar
  • 4 Lee M. Lee J. Baek B. Shin I. Synlett  2003,  325 
    Artikel in Thieme ConnectGoogle Scholar
  • 5a Shin I. Lee J. Synlett  2000,  1297 
    Google Scholar
  • 5b Lee M. Lee J. Shin I. Synlett  2002,  1463 
    Google Scholar
  • 6a Peri F. Cipolla L. Rescigno M. La Ferla B. Nicotra F. Bioconjugate Chem.  2001,  12:  325 
    Google Scholar
  • 6b Cipolla L. Rescigno M. Leone A. Peri F. La Ferla B. Nicotra F. Bioorg. Med. Chem.  2002,  10:  1639 
    Google Scholar
  • 7 Niikura K. Kamitani R. Kurogochi M. Uematsu R. Shinohara Y. Nakagawa H. Deguchi K. Monde K. Kondo H. Nishimura S.-I. Chem. Eur. J.  2005,  11:  3825 
    CrossrefPubMedGoogle Scholar
  • 8 Shao J. Tam JP. J. Am. Chem. Soc.  1995,  117:  3893 
    CrossrefGoogle Scholar
  • 9 Esser-Kahn AP. Francis MB. Angew. Chem. Int. Ed.  2008,  47:  3751 
    CrossrefPubMedGoogle Scholar
  • 10 Knör S. Modlinger A. Poethko T. Schottelius M. Wester H.-J. Kessler H. Chem. Eur. J.  2007,  13:  6082 
    CrossrefPubMedGoogle Scholar
  • 11a Liu F. Stephen AG. Fisher RJ. Burke TR. Bioorg. Med. Chem. Lett.  2008,  18:  1096 
    Google Scholar
  • 11b Liu F. Stephen AG. Waheed AA. Aman MJ. Freed EO. Fisher RJ. Burke TR. ChemBioChem  2008,  9:  2000 
    Google Scholar
  • 12a Rodriguez EC. Marcaurelle LA. Bertozzi CR. J. Org. Chem.  1998,  63:  7134 
    Google Scholar
  • 12b Duléry V. Renaudet O. Philouze C. Dumy P. Carbohydr. Res.  2007,  342:  894 
    Google Scholar
  • 13a Brask J. Jensen KJ. J. Pept. Sci.  2000,  6:  290 
    Google Scholar
  • 13b Brask J. Jensen KJ. Bioorg. Med. Chem. Lett.  2001,  11:  697 
    Google Scholar
  • 13c Tofteng AP. Hansen TH. Brask J. Nielsen J. Thulstrup PW. Jensen KJ. Org. Biomol. Chem.  2007,  5:  2225 
    Google Scholar
  • 13d Jiménez-Castells C. de la Torre BG. Gutiérrez Gallego R. Andreu D. Bioorg. Med. Chem. Lett.  2007,  17:  5155 
    Google Scholar
  • 14a Xie J. Eur. J. Org. Chem.  2002,  3411 
    Google Scholar
  • 14b Xie J. Carbohydr. Res.  2003,  338:  399 
    Google Scholar
  • 14c Durrat F. Xie J. Valéry JM. Tetrahedron Lett.  2004,  45:  1477 
    Google Scholar
  • 14d Ménand M. Blais J.-C. Hamon L. Valéry J.-M. Xie J. J. Org. Chem.  2005,  70:  4423 
    Google Scholar
  • 14e Ménand M. Blais J.-C. Valéry J.-M. Xie J. J. Org. Chem.  2006,  71:  3295 
    Google Scholar