Practical stereoselective synthesis of alpha-linked C-glucosamine propionic acid esters: conversion to GLA-60 derivatives.
Radical C-glycosylation of glucosamine derivatives by acrylic acid esters gave the corresponding 3-(alpha-C-glucosyl)-propionate derivatives in moderate yields. One of them was used as a versatile synthon for GLA-60 derivatives. However, the biological activity of these compounds as LPS-antagonists was disappointing.
Wakabayashi
Takanori
T
Exploratory Chemistry Research Laboratories, Sankyo Co. Ltd., Hiromachi 1-2-58, Shinagawa-ku, Tokyo 140-8710, Japan.
Shiozaki
Masao
M
Kurakata
Shin-ichi
S
D004952:Esters / Q000138:chemical synthesis* / Q000494:pharmacology; D005944:Glucosamine / Q000737:chemistry*; D006031:Glycosylation; D006801:Humans; D008050:Lipid A / Q000031:analogs & derivatives* / Q000737:chemistry* / Q000494:pharmacology; D008070:Lipopolysaccharides / Q000037:antagonists & inhibitors / Q000494:pharmacology; D011422:Propionates / Q000737:chemistry*; D013237:Stereoisomerism; D014409:Tumor Necrosis Factor-alpha / Q000819:agonists / Q000096:biosynthesis; D020298:U937 Cells / Q000187:drug effects
D004952:Esters; D008050:Lipid A; D008070:Lipopolysaccharides; D011422:Propionates; D014409:Tumor Necrosis Factor-alpha; C056260:GLA 60; C029658:propionic acid; D005944:Glucosamine