Lewis-O-核心-1苏氨酸的合成：O-连接型Lewis糖肽的一个构建模块。
Synthesis of Lewis-O-Core-1 threonine: A building block for O-linked Lewis glycopeptides.
作者信息
Sardar Mohammed Y R, Krishnamurthy Venkata R, Park Simon, Mandhapati Appi Reddy, Wever Walter J, Park Dayoung, Cummings Richard D, Chaikof Elliot L
机构信息
Department of Surgery, Center for Drug Discovery and Translational Research, Beth Israel Deaconess Medical Center, Harvard Medical School, 110 Francis Street, Suite 9F, Boston, MA 02215, USA; Wyss Institute of Biologically Inspired Engineering, Harvard University, 110 Francis Street, Suite 9F, Boston, MA 02115, USA.
Department of Surgery, Center for Drug Discovery and Translational Research, Beth Israel Deaconess Medical Center, Harvard Medical School, 110 Francis Street, Suite 9F, Boston, MA 02215, USA.
出版信息
Carbohydr Res. 2017 Nov 27;452:47-53. doi: 10.1016/j.carres.2017.10.002. Epub 2017 Oct 10.
Lewis (Le) is a branched trisaccharide Galβ1→4(Fucα1→3)GlcNAc that is expressed on many cell surface glycoproteins and plays critical roles in innate and adaptive immune responses. However, efficient synthesis of glycopeptides bearing Le remains a major limitation for structure-function studies of the Le determinant. Here we report a total synthesis of a Le pentasaccharide 1 using a regioselective 1-benzenesulfinyl piperidine/triflic anhydride promoted [3 + 2] glycosylation. The presence of an Fmoc-threonine amino acid facilitates incorporation of the pentasaccharide in solid phase peptide synthesis, providing a route to diverse O-linked Le glycopeptides. The described approach is broadly applicable to the synthesis of a variety of complex glycopeptides containing O-linked Le or sialyl Lewis (sLe).
Lewis（Le）是一种分支三糖Galβ1→4（Fucα1→3）GlcNAc，在许多细胞表面糖蛋白上表达，在先天性和适应性免疫反应中起关键作用。然而，有效合成带有Le的糖肽仍然是Le决定簇结构-功能研究的主要限制。在此，我们报道了使用区域选择性1-苯亚磺酰基哌啶/三氟甲磺酸酐促进的[3 + 2]糖基化反应全合成Le五糖1。Fmoc-苏氨酸氨基酸的存在有助于五糖在固相肽合成中的掺入，为多种O-连接的Le糖肽提供了一条途径。所描述的方法广泛适用于合成含有O-连接的Le或唾液酸化Lewis（sLe）的各种复杂糖肽。
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