DOI QR코드

DOI QR Code

Construction of 6-Triazole-Linked Mannopyranosyl Serine and Threonine as Novel Sugar Amino Acid Mimics

  • Deng, Qiong (Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology) ;
  • Zheng, Rong-Rong (Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology) ;
  • Ding, Na-Na (Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology) ;
  • He, Xiao-Peng (Department of Pharmaceutical Engineering, School of Pharmacy, East China University of Science and Technology) ;
  • Chen, Guo-Rong (Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology)
  • Published : 2010.04.20

Abstract

Keywords

References

  1. Lohof, E.; Burkhart, F.; Born, M. A.; Planker, E.; Kessler, H.Advances in Amino Acid Mimetics and Peptidomimetics; Abell,A., Ed.; JAI Press Inc.: Stanford, Connecticut, 1999; Vol. 2, pp 263.
  2. Varski, A. Glycobiology 1993, 3, 97. https://doi.org/10.1093/glycob/3.2.97
  3. Dwek, R.-A. Chem. Rev. 1996, 96, 683. https://doi.org/10.1021/cr940283b
  4. Schweizer, F. Angew. Chem. Int. Ed. 2002, 41, 231.
  5. Gruner,S. A. W.; Locardi, E.; Lohof, E.; Kessler, H. Chem. Rev. 2002, 102,491. https://doi.org/10.1021/cr0004409
  6. Gervay-Hague, J.; Weathers, T. M., Jr. J. Carbohydr.Chem. 2002, 7-9, 867.
  7. Rostovtsev, V. V.; Green, L. G.; Fkin, V. V.; Sharpless, K. B. Angew.Chem. Int. Ed. 2002, 41, 2596. https://doi.org/10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4
  8. Dondoni, A. Chem. Asian J. 2007, 2, 700. https://doi.org/10.1002/asia.200700015
  9. Meldal, M.;Tornoe, C. W. Chem. Rev. 2008, 108, 2952. https://doi.org/10.1021/cr0783479
  10. Janaina, V. A.; Denis, S.; Sebastiao, J. M.; Rajendra, M. S.Synthesis 2007, 17, 2647.
  11. Kuijpers, B. H. M.; Groothuys, S.;Keereweer, A. R.; Quaedflieg, P. J. L. M.; Blaauw, R. H.; van Delft,F. L.; Rutjes, F. P. J. T. Org. Lett. 2004, 6, 3123. https://doi.org/10.1021/ol048841o
  12. Dondoni, A.;Giovannini, P. P.; Massi, A. Org. Lett. 2004, 6, 2929. https://doi.org/10.1021/ol048963g
  13. Polina, I. A.; Vadim, V. K.; Leonid, O. K. Carbohydr. Res. 2009,344, 240. https://doi.org/10.1016/j.carres.2008.10.027
  14. Paulsen, H. Angew. Chem. Int. Ed. 1990, 29, 823. https://doi.org/10.1002/anie.199008233
  15. Hart, G. W.; Housley, M. P.; Slawson, C. Nature 2007, 446, 1017. https://doi.org/10.1038/nature05815
  16. Kuijpers, B. H. M.; Groothuys, S.; Hawner, C.; ten Dam, J.; Quaedflieg,P. J. L. M.; Schoemaker, H. E.; van Delft, F. L.; Rutjes, F.P. J. T. Org. Process Res. Dev. 2008, 12, 503. https://doi.org/10.1021/op700249f
  17. Li, C.; Tang, J.; Xie, J. Tetrahedron 2009, 65, 7935. https://doi.org/10.1016/j.tet.2009.07.054
  18. McDevitt, P. T.; Lansbury, Jr. J. Am. Chem. Soc. 1996, 118, 3818. https://doi.org/10.1021/ja9525622
  19. Lin, L.; Shen, Q.; Chen, G. R.; Xie, J. Bioorg. Med. Chem. 2008,16, 9757. https://doi.org/10.1016/j.bmc.2008.09.066
  20. Kuijpers, B. H. M.; Groothuys, S.; Soede, A. C.;Laverman, P.; Boerman, O. C.; van Delft, F. L.; Rutjes, F. P. J. T.Bioconjugate. Chem. 2007, 18, 1847. https://doi.org/10.1021/bc700154u

Cited by

  1. -Glycoside Hybrids via Click Chemistry as Novel PTP1B Inhibitors vol.29, pp.6, 2011, https://doi.org/10.1002/cjoc.201190228
  2. Azide- and Alkyne-Derivatised α-Amino Acids vol.2012, pp.23, 2012, https://doi.org/10.1002/ejoc.201200496
  3. Microwave-Accelerated Click Chemistry: Expeditious Synthesis of Novel Triazole-linked Salicylic β-D-O-Glycosides with PTP1B Inhibitory Activity vol.31, pp.11, 2010, https://doi.org/10.5012/bkcs.2010.31.11.3359
  4. Monosaccharide as a Central Scaffold Toward the Construction of Salicylate-Based Bidentate PTP1B Inhibitors via Click Chemistry vol.32, pp.3, 2010, https://doi.org/10.5012/bkcs.2011.32.3.1000