Bousquet E, Khitri M, Lay L, Nicotra F, Panza L, Russo G
Istituto di Chimica Farmaceutica e Toss., Catania, Italy.
Carbohydr Res. 1998 Oct;311(4):171-81. doi: 10.1016/s0008-6215(98)00218-3.
A new and more versatile synthesis of beta-D-ManpNAc-(1-->4)-alpha-D-Glcp-(1-->2)-alpha-L-Rhap, the trisaccharide repeating unit of the Streptococcus pneumoniae type 19F capsular polysaccharide, is described. The present approach allows a simple access to different fragments containing the trisaccharide and the conjugation of the product(s) to a protein through the selective manipulation of the anomeric position at the reducing end and of the HO-4 function at the nonreducing end. The synthetic scheme shows an efficient application of the sulfoxide method for the stereoselective and high yielding formation of the glycosidic linkages.
本文描述了一种新型且更具通用性的β-D-甘露糖胺-（1→4）-α-D-葡萄糖-（1→2）-α-L-鼠李糖的合成方法，该三糖是肺炎链球菌19F型荚膜多糖的重复单元。目前的方法通过对还原端异头位置和非还原端HO-4官能团的选择性操作，能够简单地获得包含该三糖的不同片段，并将产物与蛋白质偶联。合成方案展示了亚砜法在糖苷键立体选择性和高产率形成中的有效应用。
