Synthesis of α-D-Ga1p-(1→3)-β-D-Ga1f-(1→3)-D-Man, a terminal trisaccharide of Leishmania type-2 glycoinositolphospholipids
Synthesis of α-D-Ga1p-(1→3)-β-D-Ga1f-(1→3)-D-Man, a terminal trisaccharide of Leishmania type-2 glycoinositolphospholipids
复制标题
DOI：
10.1021/jo016290z
复制
发表时间：
2002-06-28
影响因子：
3.6
通讯作者：
de Lederkremer, RM
中科院分区：
文献类型：
--
作者：
Gandolfi-Donadio, L;Gallo-Rodriguez, C;de Lederkremer, RM
本文描述了存在于2型糖肌醇磷脂和利什曼原虫脂磷酸聚糖核心中的α - d - galp -(1—>3)- β - d - galf -(1—>3)- d - man的合成。采用糖基醛内酯法，然后用二异戊硼烷还原内酯，引入半乳糖呋喃基内酯单元，采用三氯乙酸酯法进行o -糖苷化反应。本文报道了一种高效合成O-D-Galf-(1—>3)- d - man单元的方法，该单元也存在于克氏锥虫的脂肽磷酸聚糖中。
The synthesis of alpha-D-Galp-(1-->3)-beta-D-Galf-(1-->3)-D-Man, present in the type-2 glycoinositolphospholipids and in the core of the lipophosphoglycan of Leishmania, is described. The glycosyl aldonolactone approach, followed by reduction of the lactone with diisoamylborane, was utilized for the introduction of the internal galactofuranosyl unit and the trichloroacetimidate method for the O-glycosidation reaction. A high-yield synthesis of the O-D-Galf-(1-->3)-D-Man unit, also present in the lipopeptidophosphoglycan of Trypanosoma cruzi, is reported.