Practical total synthesis of (2S,3S,4R)-1-O-(alpha-D-galactopyranosyl)-N-hexacosanoyl-2-amino-1,3,4-octadecanetriol, the antitumorial and immunostimulatory alpha-galactosylceramide, KRN7000

被引:49
作者
Morita, M [1 ]
Sawa, E [1 ]
Yamaji, K [1 ]
Sakai, T [1 ]
Natori, T [1 ]
Koezuka, Y [1 ]
Fukushima, H [1 ]
Akimoto, K [1 ]
机构
[1] KIRIN BREWERY CO LTD, PHARMACEUT RES LAB, TAKASAKI, GUMMA 37012, JAPAN
关键词
KRN7000; agelasphins; alpha-galactosylceramide; practical total synthesis; D-lyxose;
D O I
10.1271/bbb.60.288
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
A practical total synthesis of (2S,3S,4R)-1-O-(alpha-D-galactopyranosyl)-N-hexacosanoyl-2-amino-1,3,4-octadecanetriol (KRN7000), an antitumorial and immunostimulatory glycosphingolipid derived from agelasphins, was achieved in 14 steps starting from D-lyxose in a 16% overall yield.
引用
收藏
页码:288 / 292
页数:5
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