Synthetic studies on glycosphingolipids from protostomia phyla: synthesis of neogala-series glycolipid analogues containing a mannose residue from the earthworm Pheretima hilgendorfi.
Two kinds of glycosphingolipid analogues from the earthworm Pheretima hilgendorfi were synthesized as follows: the trisaccharide 2-(tetradecyl)hexadecyl alpha-D-mannopyranosyl-(1-->4)-beta-D-galactopyranosyl-(1-->6)-beta-D- galactopyranoside (13) and the tetrasaccharide 2-(tetradecyl) hexadecyl alpha-D-galactopyranosyl-(1-->6)-[alpha-D-mannopyranosyl-(1-->4)]-beta-D - galactopyranosyl-(1-->6)-beta-D-galactopyranoside (20) were synthesized by stepwise condensation of suitably protected monosaccharide units. A 2-(trimethylsilyl)ethyl 2,3,4-tri-O-benzoyl-beta-D-galactopyranoside derivative (5) was used as the glycosyl acceptor and thiophenyl derivatives of D-galactose and D-mannose were used as donors respectively.
Hada
N
N
Kyoritsu College of Pharmacy, Tokyo, Japan.
Matsusaki
A
A
Sugita
M
M
Takeda
T
T
D000818:Animals; D002240:Carbohydrate Sequence; D006028:Glycosphingolipids / Q000138:chemical synthesis* / Q000737:chemistry; D008358:Mannose / Q000737:chemistry*; D008969:Molecular Sequence Data; D009835:Oligochaeta / Q000737:chemistry*
D006028:Glycosphingolipids; D008358:Mannose