Neuraminic acid and related compounds. V. Syntheses of biologically active sialosyl-glycerol derivatives and galactosyl-glycerol derivative.
New 1-acyl-sialosyl-glycerol derivatives (1a--d alpha, 1a--d beta, 2 alpha, 2 beta, which mimic the structure of the capsular polysaccharide of group C meningococcal were synthesized by the use of a chiral glycerol derivative, and were found to have phospholipases A2 and C inhibitory activities. Furthermore, synthesis of 2-palmitoyl-sialosyl-glycerol derivative (4 alpha, 4 beta, 5 alpha, 5 beta), galactosyl-glycerol derivative (6), and sialosyl-galactosyl-glycerol derivative (7) were carried out to examine the difference between these activities. Among these sialosyl derivatives, 3-palmitoyl-sialosyl-glycerol derivatives (1--3 alpha, 1--3 beta) demonstrated the most potent inhibitory activities.
Shimizu
C
C
School of Pharmaceutical Sciences, University of Shizuoka, Japan.
Ohta
N
N
Achiwa
K
K
D005697:Galactosides / Q000737:chemistry; D005990:Glycerol / Q000737:chemistry; D009438:Neuraminic Acids / Q000138:chemical synthesis* / Q000494:pharmacology; D010741:Phospholipases A / Q000037:antagonists & inhibitors; D012794:Sialic Acids / Q000737:chemistry; D010738:Type C Phospholipases / Q000037:antagonists & inhibitors
D005697:Galactosides; D009438:Neuraminic Acids; D012794:Sialic Acids; D010741:Phospholipases A; D010738:Type C Phospholipases; D005990:Glycerol