Bergh A, Magnusson B G, Ohlsson J, Wellmar U, Nilsson U J
Bioorganic Chemistry, Lund University, Sweden.
Glycoconj J. 2001 Aug;18(8):615-21. doi: 10.1023/a:1020639603070.
The present paper describes the synthesis and use of the hydrophobic squaric decyl ester glycosides in neoglycoconjugate chemistry. The 2-aminoethyl glycosides of alpha-D-mannopyranose, lactose, globotriose, globotetraose, GM3, and sialyl Lewis(x), as well as the 2-(2-aminoethylthio)ethyl glycoside of alpha-D-mannopyranose, beta-D-glucopyranose, and galabiose were reacted with squaric acid didecyl ester to afford the hydrophobic squaric decyl ester glycosides. These glycosides were efficient reagents for the conjugation to amino-functional microtiter plates, BSA and aminated Sepharose EAH 4B. The decyl ester moiety of the squaric decyl ester glycosides constitutes a traceless hydrophobic tag, which has the major advantage, as compared to the corresponding ethyl esters, that it enables easy purification of the glycosides with silica chromatography and that unreacted excesses glycosides from conjugation reaction mixtures can easily be recovered by means of C18 solid phase extraction.
本文描述了疏水方形癸酯糖苷在新糖缀合物化学中的合成与应用。α-D-甘露吡喃糖、乳糖、球三糖、球四糖、GM3和唾液酸化路易斯(x)的2-氨基乙基糖苷，以及α-D-甘露吡喃糖、β-D-葡萄糖吡喃糖和半乳糖的2-(2-氨基乙硫基)乙基糖苷与方形二酸二癸酯反应，得到疏水方形癸酯糖苷。这些糖苷是用于与氨基功能微量滴定板、牛血清白蛋白和胺化琼脂糖EAH 4B偶联的有效试剂。方形癸酯糖苷的癸酯部分构成一个无痕疏水标签，与相应的乙酯相比，其主要优点是能够通过硅胶色谱轻松纯化糖苷，并且可以通过C18固相萃取轻松回收偶联反应混合物中未反应的过量糖苷。
