School of Chemical Sciences, The University of Auckland, 23 Symonds Street, Auckland, New Zealand.
J Org Chem. 2012 Sep 7;77(17):7564-71. doi: 10.1021/jo3013435. Epub 2012 Aug 17.
The efficient synthesis of multivalent neoglycoconjugates of MUC1 is reported, which utilizes Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition (CuACC) of azide-functionalized GlcNAc-centered neoglycotetrasaccharide clusters to the MUC1 peptide sequence that was equipped with a propargylglycine residue for "click chemistry". In turn the azido-GlcNAc-centered neoglycoclusters were assembled by reaction of a GlcNAc core containing peripheral propargyl functionalities with an appropriate azido-functionalized monosaccharide. The resulting suitably substituted tetrasaccharyl triazole cluster can be easily appended to a range of acetylene-functionalized peptides to produce neoglycoconjugates of biologically important glycopeptides. As proof of principle, the click neoglycoclusters prepared herein were ligated to the MUC1 peptide sequence.
报道了一种有效的多价 MUC1 型糖缀合物的合成方法，该方法利用 Cu(I)-催化的叠氮-炔 1,3-偶极环加成（CuACC），将叠氮功能化的 GlcNAc 为中心的新糖四聚糖簇连接到带有炔丙氨酸残基的 MUC1 肽序列上，用于“点击化学”。反过来，叠氮 GlcNAc 为中心的新糖簇通过含有外围炔丙基官能团的 GlcNAc 核心与适当的叠氮功能化单糖反应来组装。由此得到的适当取代的四糖三唑簇可以很容易地连接到一系列乙炔功能化的肽上，从而产生生物重要糖肽的新糖缀合物。作为原理验证，本文制备的点击新糖簇被连接到 MUC1 肽序列上。
