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.
The front cover picture, provided by Chun‐Cheng Lin, Ching‐Ching Yu and co‐workers, illustrates a bifunctional sulfo‐fluorous affinity (SOFA) tag‐assisted enzymatic synthesis strategy for the facile preparation of complex glycans. The SOFA tag, which they developed, shows good water solubility and contains a photo‐cleavable linker for release of the glycan after fluorous solid‐phase extraction. Details of this work can be found in the full paper on pages 2313–2323 (K.‐L. Hou, P.‐Y. Chiang, C.‐H. Lin, B.‐Y. Li, W.‐T. Chien, Y.‐T. Huang, C.‐C. Yu, C.‐C. Lin, Adv. Synth. Catal. 2018, 360, 2313–2323; DOI: 10.1002/adsc.201800085).
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