Synthesis of galactosylglycerol from Melibiose as M-5 Intermediate

Melibiose로부터 M-5중간체 galactosylglycerol의 합성

  • 차배천 (상지대학교 생명자원과학대학 응용동물과학부)
  • Published : 2001.12.01

Abstract

The galactolipid M-5, which showed anti-inflammatory activity is glycoglycerolipid isolated from the Okinawa marine sponge Phyllospongia foliascens. Glycolipids have been synthesized by various methods, especially it were generally known that synthetic method of M-5 analogue and synthetic method of various glycolipids by glycosidation after synthesis of glycerolipid part. The others, it was not suggested that synthetic method via glycosylglycerol obtained by degradation from diglycoside. This study was carried out to investigate the synthesis of galactosylglycerol from melibiose as M-5 intermediate. Synthesis of galactosylglycerol was accomplished by selective protection of hydroxy group of sugar and diol cleavage by Pb(OAc)$_4$. As a result, galactosylglycerol was synthesized by 8 steps pathway and their structures were elucidated by analysis instrument.

Keywords

References

  1. Carbohydr. Res. v.312 no.167 Joint Commission on Biochemical Nomenclature : Nomenclature of glycoliqpids IUPAC-IUBMB
  2. EMBO J. v.11 no.3845 Involvement of a neutral glycolipid in differential cell adhesion in the Xenopus blastula Turner, A. P.;Brown, D.;Heasman, J.;Cook, G. M.;Evans, J.;Vickers, L.;Wylie, C. C.
  3. Glycobiolog v.3 no.97 Biological roles of oilgosaccharides : all of the theories are correct Varki, A.
  4. Anal. Biochem. v.241 no.59 Detection of glycolipids as biotinylated derivatives using enhanced chemiluminescence Hernandez, L. E.;Brewin, N. J.;Drobak, B. K.
  5. Chem. Pharm. Bull. v.31 no.552 Marine natural products. XI. An antiinflammatory scalarane-type bishomosesterterpene, foliaspongin, from the okinawa marine sponge Phyllospongia foliascens (Pallas) Kikuchi, H.;Tsukitani, Y.;Shimizu, I.;Kobayashi, M.;Kitagawa, I.
  6. Chem. Pharm. Bull. v.41 no.1545 Studies on Glycolipids VII. Isolation of two new sulfoquinovosyl diacylglycerols from the green alga Chlorella vulgaris Morimoto, T.;Murakami, N.;Nagatsu, A.;Sakakibara, J.
  7. J. Nat. Prod. v.57 no.534 A monogalactosyl diacylglycerol from a cultured marine dinoflagellate, Scrippsiella trochoidea Oshima, Y.;Yamada, S.;Matsunaga, K.;Moriya, T.;Ohizumi, Y.
  8. Tetrahedron v.52 no.7921 Three new glycolipids from a red sea sponge of the genus erylus Goobes, R.;Rudi, A.;Kashman, Y.
  9. 蛋白質 核酸 酵素 v.19 no.499 スフインユ糖脂肪質の化學(I) 林陽;松原淑子
  10. Chem. Phys. Lipids v.26 no.287 Synthesis of glycolipids Gigg, R.
  11. J. Carbohydr. Res. v.16 no.230 Synthesis of the methyl thioglycosides of deoxy-N-acetyl-neurmic acids use as glycosyl donors Hasegawa, A.;Adachi, K.;Yoshida, M.;Koso, M.
  12. Chem. Phys. Lipids v.72 no.111 Synthesis of 1,3-di-O-alky-2-O-(beta-glycosyl)glycerols bearing oligosaccharides as hydrophilic groups Minamikawa, H.;Murakami, T.;Hato, M.
  13. Chem. Pharm. Bull. v.40 no.1166 Syntheses of a glycerophospholipid, C16-platelet activating factor and a palmitoyl analogue of M-5, an anti-inflammatory glyceroglycolipid Shibuya, H.;Kawashima, K.;Narita, N.;Kitagawa, I.
  14. Chem. Pharm. Bull. v.47 no.1265 Synthetic studies on glycosphingolipids from Protostomia phyla : Synthesis of neogala-series glycolipid analogues containing a mannose residue from the earthworm Pheretima hilgendorfi Hada, N.;Matsusaki, A.;Sugita, M.;Takeda, T.
  15. Biochim. Biophys. Acta. v.10 no.152 Commission on Biochemical Nomenclature : The nomenclature of lipids IUPAC-IUB
  16. Tetrahedrom Lett. v.45 no.3937 Lilioside A and B, two new glycerol glucosides isolated from Lilium longiflorum Thunb Kaneda, M.;Mizutami, K.;Takahashi, Y.;Kurono, G.;Nishikawa, Y.
  17. Chem. Pharm. Bull. v.36 no.4841 New phenylpropanoid glycerol glucosides from the bulbs of Lilium species Shimomura, H.;Sashida, Y.;Mimaki, Y.;Kudo, Y.;Maeda, K.
  18. J. Bacteriol. v.176 no.6877 A prominent role for glucosylglycerol in the adaptation of Pseudomonas mendocina SKB70 to osmotic stress Pocard, J. A.;Smith, L. T.;Smith, G. M.;Le Rudulier, D.
  19. J. Carbohydr. Chem. v.17 no.937 Synthesis of glycosyl glycerols and related glycolipids Suhr, R.;Scheel, O.;Thiem, J.
  20. Bioorg. Med. Chem. v.7 no.1867 Chemoenzymatic synthesis and antitumor promoting activity of 6'-and 3-esters of 2-O-beta-D-glucosylglycerol Colombo, D.;Compostella, F.;Ronchetti, F.;Scala, A.;Toma, L.;Tokuda, H.;Nishino, H.