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Water‐Soluble Sulfo‐Fluorous Affinity (SOFA) Tag‐Assisted Enzymatic Synthesis of Oligosaccharides
Advanced Synthesis & Catalysis ( IF 5.4 ) Pub Date : 2018-03-09 , DOI: 10.1002/adsc.201800085
Kai-Ling Hou,Pei-Yun Chiang,Chien-Hung Lin,Ben-Yuan Li,Wei-Ting Chien,Yu-Ting Huang,Ching-Ching Yu,Chun-Cheng Lin

Herein, we report a bifunctional sulfo‐fluorous affinity (SOFA) tag‐assisted enzymatic synthesis and purification strategy for the facile preparation of bioactive glycans using fluorous solid‐phase extraction (FSPE). The incorporation of a sulfonate moiety onto the heavy fluorous tag significantly increases its water solubility, which allows the broad use of the inherently hydrophobic fluorous tag in aqueous buffers. In addition, the SOFA tag contains a photocleavable linker, enabling the easy release of amino‐functionalized oligosaccharides by UV irradiation. The SOFA tag was used in the synthesis of both negatively charged and neutral glycans to demonstrate its broad utility as an acceptor toward six different glycosyltransferases, significantly improving the feasibility of the preparation of complex glycans using FSPE. All the reactions were performed in an aqueous buffer, a minimum amount of methanol was used to purify the products, and the SOFA tag was easily recovered after photo‐irradiation. Thus, the entire synthetic process is environmentally benign.

中文翻译:

水溶性硫氟亲和力(SOFA)标签辅助酶法合成寡糖

本文中,我们报告了一种双功能磺基-氟亲和力(SOFA)标签辅助的酶法合成和纯化策略,用于使用氟固相萃取(FSPE)轻松制备生物活性聚糖。将磺酸盐部分结合到重的氟标签上显着增加了其水溶性,这允许在水性缓冲液中广泛使用固有疏水性的氟标签。此外,SOFA标签还包含可光裂解的接头,可通过紫外线辐射轻松释放氨基官能化的寡糖。SOFA标签用于带负电荷的聚糖和中性聚糖的合成,以证明其广泛用作六种不同糖基转移酶的受体,从而显着提高了使用FSPE制备复杂聚糖的可行性。所有反应均在水性缓冲液中进行,使用最少量的甲醇纯化产物,光辐照后很容易回收SOFA标签。因此,整个合成过程对环境无害。
更新日期:2018-03-09
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