Synthesis of phosphatidylinositol mannosides (PIMs)

Carbohydrate Research

Volumn 338, Issue 23, 2003, Pages 2557-2569

  Stadelmaier, Andreas ^a   Schmidt, Richard R ^a  

^a UNIVERSITY OF KONSTANZ   (Germany)

Author keywords

Glycosidation; Phosphatidylinositol; Phosphatidylinositol mannoside; Structural assignment; Synthesis

Indexed keywords

ALCOHOLS; ISOMERS; SYNTHESIS (CHEMICAL);

ENANTIOMERS;

CARBOHYDRATES;

1,2:4,5 DI O CYCLOHEXYLIDENE INOSITOL; CARBOHYDRATE DERIVATIVE; INOSITOL DERIVATIVE; LIRIODENTRITOL; MANNOSIDE; PHOSPHATIDYLINOSITOL MANNOSIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; ENANTIOMER; PRIORITY JOURNAL; SYNTHESIS;

EID: 0345528938     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2003.06.002     Document Type: Article

References (43)

1. Draper P. The Anatomy of Mycobacteria. Ratledge C., Standford J. The Biology of Mycobacteria. 2:1982;9-52 Academic Press, London.
2. Brennan P.J., Nikaido H. Annu. Rev. Biochem. 64:1995;887-888.
3. Chatterjee D., Khoo K.-H. Cell. Mol. Life Sci. 58:2001;2018-2042.
4. Chatterjee D., Khoo K.-H. Glycobiology. 8:(2):1998;113-120.
5. Brennan P.J., Ballou C.E. J. Biol. Chem. 242:1967;3046-3056.
6. Besra G.S., Morehouse C.B., Rittner C.M., Waechter C.J., Brennan P.J. Am. Soc. Biochem. Mol. Biol. 272:1997;18460-18466.
7. Theler, J. -M.; Brennan, P. J.; Nasir-ud-Din; Ilangumaran, S.; Arni, S.; Poincelet, M.; Hoessli, D. C. J. Immunol. 1995, 155, 1334-1342.
8. Stadelmaier, A. Diplomarbeit, Universität Konstanz, 1999.
9. Stadelmaier, A. Dissertation, Universität Konstanz, 2003.
10. Stepanov A.E., Shvets V.I., Evstigneeva R.P. Zh. Obshch. Kim. 47:1977;1653-1656.
11. Zamyatina A.Y., Shvets V.I. Chem. Phys. Lipids. 76:1995;225-240.
12. Elie C.J.J., Dreef C.E., Verduyn R., Van der Marel G.A., Van Boom J.H. Tetrahedron. 45:1989;3477-3486.
13. Elie C.J.J., Verduyn R., Dreef C.E., Van der Marel G.A., Van Boom J.H. J. Carbohydr. Chem. 11:1992;715-739.
14. Watanabe Y., Yamamoto T., Ozaki S. J. Org. Chem. 61:1996;14-15.
15. Watanabe Y., Yamamoto T., Okazaki T. Tetrahedron. 53:1997;903-918.
16. Massy D.J.R., Wyss P. Helv. Chim. Acta. 73:1990;1037-1057.
17. Mayer T.G., Schmidt R.R. Liebigs Ann. Recueil. 1997;859-863.
18. Pekari K., Schmidt R.R. Recent results in glycosyl phosphatidyl inositol (GPI) anchor synthesis. Kokotos G., Constantinou-Kokotou V. Lipases and Lipids: Structure, Function and Biotechnological Applications. 2000;233-252 Crete University Press, Heraklion.
19. Pekari K., Tailler D., Weingart R., Schmidt R.R. J. Org. Chem. 66:2001;7432-7442.
20. Maki T., Iwasaki F., Matsumura Y. Tetrahedron Lett. 39:1998;5601-5604.
21. Mayer, T. G.; Kratzer, B.; Schmidt, R. R. Angew. Chem. 1994, 106, 2289-2293; Angew. Chem. Int. Ed. Engl. 1994, 33, 2177-2181.
22. Mayer, T. G.; Kratzer, B.; Schmidt, R. R. Angew. Chem. 1994, 106, 2289-2293; Angew. Chem. Int. Ed. Engl. 1994, 33, 2177-2181.
23. Kartha K.P.R., Jennings H.J. J. Carbohydr. Chem. 1990;777-781.
24. Borén H.B., Ekborg G., Ekland K. Acta Chem. Scand. 27:1973;2639-2644.
25. Kaur K.J., Hindsgaul O. Carbohydr. Res. 226:1992;219-231.
26. Ponpipom M.M. Carbohydr. Res. 59:1977;311-317.
27. Yamazaki F., Kitajima T., Nukada T., Ito Y., Ogawa T. Carbohydr. Res. 201:1990;31-50.
28. Schmidt R.R., Toepfer A. Tetrahedron Lett. 32:1991;3353-3356.
29. Bock K., Pederson C. J. Chem. Soc. Perkin Trans. II. 1974;293-297.
30. Yonezawa T., Morishma I. J. Mol. Spectrosc. 27:1968;210-217.
31. Albrand J.P., Cogne A., Gagnaire D., Robert J.B. Tetrahedron. 27:1971;2453-2461.
32. Mayer T.G., Weingart R., Münstermann F., Kawada T., Teymuras T., Schmidt R.R. Eur. J. Org. Chem. 10:1999;2563-2572.
33. Beaucage S.L., Caruthers M.H. Tetrahedron Lett. 22:1981;1859-1862.
34. Beaucage S.L., Iyer R.P. Tetrahedron. 49:1993;10441-10488.
35. Bannwarth W., Trzeciak A. HeIv. Chim. Acta. 70:1987;175-186.
36. Honda M., Morita H., Nagakura I. J. Org. Chem. 62:1997;8932-8936.
37. Vacca J.P., deSolms S.J., Huff J.R., Billington D.C., Baker R., Kulagowski J.J., Mawer I.M. Tetrahedron. 45:1989;5679-5702.
38. Billington D.C., Baker R., Kulagowski J.J., Mawer I.M. J. Chem. Soc., Chem. Commun. 1987;314-316.
39. Aguiló A., Martín-Lomas M., Penadés S. Tetrahedron Lett. 33:1992;401-404 Anderson, L. The Carbohydrates, Chemistry and Biochemistry, 2nd ed.; Pigman, W., Horton, D., Eds.; Academic Press, New York, 1972, Vol. 1A, pp. 519-579.
40. Plouvier V. Bull. Soc. Chim. Biol. 45:1963;1079-1118.
41. Angyal S.J., Bender V. J. Chem. Soc. 1961;4718-4720.
42. Post G.G., Anderson L. J. Am. Chem. Soc. 84:1962;471-478.
43. Post G.G., Anderson L. J. Am. Chem. Soc. 84:1962;478-480.