Lipid A and related compounds. XXIX. Synthesis of biologically active N-acylated L-asparagine-containing D-glucosamine derivatives structurally related to lipid A

Chem Pharm Bull (Tokyo). 1994 Dec;42(12):2526-31. doi: 10.1248/cpb.42.2526.

Abstract

New beta-N-acylated L-asparagine-linked D-glucosamine derivatives, in which the reducing unit of lipid A has been mimicked by a lipoamino acid, have been synthesized. Compounds 1 and 2 exhibit mitogenicity and nitric oxide (NO) productivity.

MeSH terms

  • Animals
  • Cell Division / drug effects
  • Glucosamine / analogs & derivatives
  • Glucosamine / chemical synthesis*
  • Glucosamine / pharmacology
  • In Vitro Techniques
  • Lipid A / analogs & derivatives*
  • Lipid A / chemistry
  • Lipid A / pharmacology
  • Macrophages, Peritoneal / drug effects
  • Macrophages, Peritoneal / metabolism
  • Magnetic Resonance Spectroscopy
  • Mice
  • Mitogens / chemical synthesis*
  • Mitogens / pharmacology
  • Nitric Oxide / biosynthesis*
  • Spectrometry, Mass, Fast Atom Bombardment
  • Spectrophotometry, Infrared

Substances

  • Lipid A
  • Mitogens
  • Nitric Oxide
  • Glucosamine