单糖基化α-D-吡喃糖基神经酰胺的免疫刺激活性

Immunostimulatory activities of monoglycosylated alpha-D-pyranosylceramides.

作者信息

Uchimura A, Shimizu T, Morita M, Ueno H, Motoki K, Fukushima H, Natori T, Koezuka Y

机构信息

Pharmaceutical Research Laboratory, Kirin Brewery Co., Ltd., Gunma, Japan.

出版信息

Bioorg Med Chem. 1997 Dec;5(12):2245-9. doi: 10.1016/s0968-0896(97)00169-7.

DOI:10.1016/s0968-0896(97)00169-7

PMID:9459022

Abstract

We compared the immunostimulatory effects of chemically synthesized alpha-galactosylceramides (alpha-GalCers), alpha-glucosylceramides (alpha-GluCers), 6"-monoglycosylated alpha-GalCer and 6"- or 4"-monoglycosylated alpha-GluCer and made the following observations: (1) the length of the fatty acid side chain in the ceramide portions greatly affects the immunostimulatory effects of alpha-GalCers and alpha-GluCers; (2) the configuration of the 4"-hydroxyl group of the inner pyranose moiety plays an important role in the immunostimulatory effects of monoglycosylated alpha-D-pyranosylceramides; (3) the free 4"-hydroxyl group of the inner pyranose of monoglycosylated alpha-D-pyranosylceramides plays a more important role in their immunostimulatory effects than the free 6"-hydroxyl group.

摘要

我们比较了化学合成的α-半乳糖神经酰胺（α-GalCers）、α-葡萄糖神经酰胺（α-GluCers）、6″-单糖基化α-GalCer以及6″-或4″-单糖基化α-GluCer的免疫刺激作用，并得出以下观察结果：（1）神经酰胺部分脂肪酸侧链的长度对α-GalCers和α-GluCers的免疫刺激作用有很大影响；（2）内吡喃糖部分4″-羟基的构型在单糖基化α-D-吡喃糖基神经酰胺的免疫刺激作用中起重要作用；（3）单糖基化α-D-吡喃糖基神经酰胺内吡喃糖的游离4″-羟基在其免疫刺激作用中比游离6″-羟基起更重要的作用。