Facile synthesis of stable lipid analogues possessing a range of alkyl groups: Application to artificial glycolipids

Bioorganic and Medicinal Chemistry

Volumn 10, Issue 12, 2002, Pages 4013-4022

  Azefu, Yasuo ^a   Tamiaki, Hitoshi ^a   Sato, Reiko ^b   Toma, Kazunori ^b  

^a RITSUMEIKAN UNIVERSITY   (Japan)

^b NOGUCHI INSTITUTE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; BENZOIC ACID DERIVATIVE; GLYCOLIPID; HYDROXYL GROUP; LIPID;

ARTICLE; COVALENT BOND; LIPOGENESIS; METHODOLOGY; PROTEIN INTERACTION; STEREOCHEMISTRY;

ANIMALS; BENZOIC ACIDS; CONCANAVALIN A; GLYCOCONJUGATES; GLYCOLIPIDS; KINETICS; LIPIDS; LIPOSOMES; MANNOSE; MODELS, MOLECULAR; PROTEIN BINDING; RICIN; SERUM ALBUMIN, BOVINE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0036978409     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(02)00266-3     Document Type: Article

References (23)

1. Drickamer K., Taylor M.E. Annu. Rev. Cell Biol. 9:1993;237.
2. Varki A. Glycobiology. 3:1993;97.
3. (a) Mortell K.H., Weatherman R.V., Kiessling L.L. J. Am. Chem. Soc. 118:1996;2297
4. (b) Mortell K.H., Gingras M., Kiessling L.L. J. Am. Chem. Soc. 116:1994;12053.
5. Lundquist J.J., Toone E.J. Chem. Rev. 102:2002;555.
6. A review of syntheses of sphingosine: Koskinen P.M., Koskinen A.M.P. Synthesis. 1998;1075.
7. (a) Kunitake T. Angew. Chem., Int. Ed. Engl. 31:1992;709.
8. (b) Blackburn C.C., Schnaar R.L. J. Biol. Chem. 258:1983;1180.
9. (c) Auzély-Velty R., Benvegnu T., Mackenzie G., Haley J.A., Goodby J.W., Plusquellec D. Carbohydr. Res. 314:1998;65.
10. (d) Pozsgay V. Org. Lett. 1:1999;477.
11. (a) Lockhoff O., Stadler P. Carbohydr. Res. 314:1998;13.
12. (b) Conboy J.C., McReynolds K.D., Gervay-Hague J., Saavedra S.S. J. Am. Chem. Soc. 124:2002;968.
13. Tamiaki H., Obata T., Azefu Y., Toma K. Bull. Chem. Soc. Jpn. 74:2001;733.
14. Schmidt R.R., Kinzy W. Adv. Carbohydr. Chem. Biochem. 50:1994;21.
15. (a) Toma, K.; Sato, R.; Tamiaki, H. JP Patent 2001-122889, 2001.
16. (b) Tamiaki, H.; Azefu, Y.; Toma, K.; Sato, R. JP Patent 2001-253896, 2001.
17. (c) Sato, R.; Toma, K.; Tamiaki, H. JP Patent 2002-30091, 2002.
18. (a) Kalb E., Frey S., Tamm L.K. Biochim. Biophys. Acta. 1103:1992;307.
19. (b) Kuziemko G.M., Stroh M., Stevens R.C. Biochemistry. 35:1996;6375.
20. Sharon N., Lis H. LECTINS. 1989;Chapman and Hall, London.
21. Metzger R.M., Wiser D.C., Laidlaw R.K., Takassi M.A. Langmuir. 6:1990;350.
22. 1H NMR spectrum was complex due to the cis/trans mixture (see text). At 323 K, the cis and trans conformers exchanged so rapidly in the NMR measurement time scale that the spectrum was simple.
23. MacDonald R.C., MacDonald R.I., Menco B.P.M., Takeshita K., Subbarao N.K., Hu L.R. Biochim. Biophys. Acta. 1061:1991;297.