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A Short and Simple Synthesis of Branched Mannoligosaccharides with [1-13C]-Labelled Terminal mannose Units

Identyfikatory
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
Mannosylation with 2,3,4,6-tetra-O-benzoyl-_-D-[1-13C]mannopyranosyl bromide as a glycosyl donor has been used for the synthesis of 3,6-branched mannotri- and -pentaoside bearing labelled terminal mannopyranose units. Methyl 2,4-di-O-benzoyl-_-Dmannopyranoside was used as the glycosyl acceptor for the synthesis of the trisaccharide and also converted into a disaccharide precursor for the pentasaccharide.
Rocznik
Strony
275--286
Opis fizyczny
Bibliogr. 26 poz., rys.
Twórcy
autor
  • N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prosp. 47, 119991 Moscow, Russian Federation
  • N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prosp. 47, 119991 Moscow, Russian Federation
autor
  • N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prosp. 47, 119991 Moscow, Russian Federation
autor
  • N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prosp. 47, 119991 Moscow, Russian Federation
autor
  • N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prosp. 47, 119991 Moscow, Russian Federation
Bibliografia
  • 1.Audette G.F., Delbaere L.T.J. and Xiang J., Curr: Prat. Pept. Sci., 4, 11 (2003).
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  • 4. Meyer B. and Peters T., Angew. Chem. Int. Ed., 42, 864 (2003).
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  • 6. Shimizu H., 1700, 15,221 (2003).
  • 7. Homans S.W., Biachem. Soc. Trans., 26, 551 (1998).
  • 8. Bush C.A., Martin-Pastor M. and lmberty A., Ann. Rev. Biophys. Biomol. Struct., 28, 269 (1999).
  • 9. Kilpatrick D.C., Biochim. Biophys. Acta, 1572, 401 (2002).
  • 10. Tanaka H., Nishida Y. and Kobayashi K., .J. Carbohydr: Chem., 19, 413 (2000).
  • 11.Du Y., Zhang M. and Kong F., Tetrahedron, 57, 1757 (2001).
  • 12. Backinowsky L.V., Abronina P.I., Shashkov A.S., Grachev A.A., Kochetkov N.K., Nepogodiev S.A. and Stoddart J .F., Chem. Eur: J., 8, 4412 (2002) and references cited therein.
  • 13. Smiljanic N., Halila S., Moreau V. and Djedatni-Pilard F., Tetrahedron Lett., 44, 8999 (2003).
  • 14. Watt G.M. and Boons G.-.J., Carbohydr: Res., 339, 181 (2004).
  • 15. Winnik F.M., Carver J.P. and Krepinsky J.J., .J. Labelled Compds, 20, 983 (1983).
  • 16. Carver J.P., MacKenzie A.E. and Hardman K.D., Biopolymerr, 24, 49 (1985).
  • 17. Dime D.S., Rachaman E., Dime C.E., Grey A.A., Carver J.P. and Krepinsky J.J., J. Labelled Compds, 24, 725 (1986).
  • 18. Oscanon S. and Tidén A.-K., Carbohydr. Res., 247, 323 (1993).
  • 19.Yu H.N., Ling C.C. and Bundle D.R., J. Chem. Sac. Perkin Trans. 1 , 832 (2001).
  • 20. Yockot D., Moreau V., Demailly G. and Djedami-Pilard F., Org. Biomol. Chem., 1, 1810 (2003).
  • 21. Byramova N.E., Ovchinnikov M.V., Backinowsky L.V. and Kochetkov N.K., Carbohydt Res., 124, c8 (1983).
  • 22.Backinowsky L.V., Abronina P.I., Nepogodiev S.A., Grachev A.A. and Kochetkov N.K., Polish J. Chem., 73, 955 (1999).
  • 23. Ogawa T. and Sasajima K., Tetrahedron, 37, 2787 (1981).
  • 24.Kochetkov N.K., ByramovaN.E., Tsvetkov Yu.E. and Backinowsky L.V., Tetrahedron, 41,3363 (1985)
  • 25.Winnik F., Brisson J.-R., Carver J.P. and Krepinsky J.J., Carbohydr. Res., 103, 15 (1982).
  • 26. Aboitiz N., Backinowskn L.V., Al-Hashimi H.M., Schwalbe H. and Jimenez-Barbero J, II Bienal RMN, GERMN RSEQ, Univ. Santiago de Compostela, 19-22 September, 2004.
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BUJ1-0025-0114
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