Synthetic studies on glycosphingolipids from protostomia phyla: Synthesis of amphoteric glycolipid analogues from the porcine nematode, Ascaris suum

Chemical and Pharmaceutical Bulletin

Volumn 50, Issue 5, 2002, Pages 600-604

  Ohtsuka, Isao ^a   Hada, Noriyasu ^a   Ohtaka, Hiroko ^a   Sugita, Mutsumi ^b   Takeda, Tadahiro ^a  

^a KEIO UNIVERSITY   (Japan)

^b SHIGA UNIVERSITY   (Japan)

Author keywords

mannosidic linkage; Amphoteric glycosphingolipid; Ascaris suum; Chemical synthesis; Phosphocholine

Indexed keywords

2 CHLORO 2 OXO 1,3,2 DIOXAPHOSPHOLANE; CERAMIDE; GLYCOLIPID; GLYCOSPHINGOLIPID; PHOSPHATE; PHOSPHORUS DERIVATIVE; PHOSPHORYLCHOLINE; TRIMETHYLAMINE; UNCLASSIFIED DRUG; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; OLIGOSACCHARIDE;

ARTICLE; ASCARIS SUUM; DEBENZYLATION; HOST PARASITE INTERACTION; ISOLATION PROCEDURE; NEMATODE; SWINE; SYNTHESIS; ANIMAL; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

ANIMALS; ASCARIS SUUM; GLYCOLIPIDS; GLYCOSPHINGOLIPIDS; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; OLIGOSACCHARIDES; SWINE;

EID: 0036581842     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.50.600     Document Type: Article

References (30)

1. Varki A., Glycobiology, 3, 97-130 (1993).
2. Kameyama A., Ishida H., Kiso M., Hasegawa A., J. Carbohydr. Chem., 10, 549-560 (1991).
3. Tsukida T., Yoshida M., Kurokawa K., Nakai Y., Achiha T., Kiyoi T., Kondo H., J. Org. Chem., 62, 6876-6881 (1997).
4. Hayashi M., Tanaka M., Itoh M., Miyauchi H., J. Org. Chem., 61, 2938-2945 (1996).
5. Hori T., Sugita M., Kanbayashi J., Itasaka O., J. Biochem. (Tokyo), 81, 107-114 (1977).
6. Hori T., Takeda H., Sugita M., Itasaka O., J. Biochem. (Tokyo), 82, 1281-1285 (1977).
7. Hori T., Sugita M., Ando S., Kuwahara M., Kumauchi K., Sugie E., J. Biol. Chem., 256, 10979-10985 (1981).
8. Dennis R. D., Geyer R., Egge H., Menges H., Stirm S., Wiegandt H., Eur. J. Biochem., 146, 51-58 (1985).
9. Takeda T., Hada N., Ogihara Y., Chem. Pharm. Bull., 40, 1930-1933 (1992).
10. Takeda T., Hada N., Ogihara Y., Chem. Pharm. Bull., 41, 2058-2060 (1993).
11. Hada N., Takeda T., Ogihara Y., Carbohydr. Res., 258, 93-104 (1994).
12. Hada N., Hayashi E., Takeda T.. Carbohydr. Res., 316, 58-70 (1999).
13. Hada N., Matsuzaki A., Takeda T., Chem. Pharm. Bull., 47, 1265-1268 (1999).
14. Hada N., Kuroda M., Takeda T., Chem. Pharm. Bull., 48, 1160-1165 (2000).
15. Hada N., Ohtsuka I., Sugita M., Takeda T., Tetrahedoron Lett., 41, 9065-9068 (2000).
16. Hada N., Sato K., Sakushima J., Goda Y., Sugita M., Takeda T., Chem. Pharm. Bull., 49, 1464-1467 (2001).
17. Takeda T., Hada N., Ohtsuka I., Sugita M., Carbohydr. Res., submitted.
18. Sugita M., Mizunoma T., Hayata C., Hori T., Nakatani F., Aoki K., J. Jpn. Oil. Chem. Soc. (Yukagaku), 43, 495-501 (1994).
19. Sugita M., Nishida M., Hori T., J. Biochem. (Tokyo), 92, 327-334 (1982).
20. Kurimoto A., Kawakami Y., Dulaney T J., Miyake A., Sugita M., J. Jpn. Oil. Chem. Soc., 49, 127-135 (2000).
21. Lochnit G., Dennis R. D., Ulmer A. J., Geyer R., J. Biol. Chem., 273, 466-474 (1998).
22. Ito Y., Ando H., Wada M., Kawai T., Ohnishi Y., Nakahara Y., Tetrahedron., 57, 4123-4132 (2001).
23. Srivastava O., Hindsgaul O., Carbohydr. Res., 179, 137-161 (1988).
24. Jansson K., Ahlfors S., Kihlberg T., Magnusson M., J. Org. Chem., 53, 5629-5647 (1988).
25. Jansson K., Frejd T., Kihlberg J., Magnusson G., Tetrahedron Lett., 29, 361-362 (1988).
26. Schmidt R. R., Grundler G., Synthesis., 1981, 885-887 (1981).
27. Lergenmuller M., Nukada T., Kuramochi K., Dan A., Ogawa T., Ito Y., Eur. J. Org. Chem., 1999, 1367-1376 (1999).
28. Bock K., Pedersen C., J. Chem. Soc., Perkin Trans, 2, 1974, 293-297 (1974).
29. Sefert J., Lergenmuller M., Ito Y., Angew. Chem. Int. Ed., 39, 531-534 (2000).
30. Menger F. M., Chen. X. Y., Brocchini S., Hopkins H. P., Hamilton D., J. Am. Chem. Soc., 115, 6600-6608 (1993).