Department of Chemistry, University of California, One Shields Avenue, Davis, CA, 95616, USA.
Department of Chemistry, University of California, One Shields Avenue, Davis, CA, 95616, USA.
Carbohydr Res. 2019 Jun 1;479:41-47. doi: 10.1016/j.carres.2019.05.002. Epub 2019 May 16.
A sialyltransferase acceptor tagging and two-step enzymatic reaction strategy has been developed for multigram-scale chemoenzymatic synthesis of 2,7-anhydro-N-acetylneuraminic acid (2,7-anhydro-Neu5Ac), a compound that can serve as a sole carbon source for the growth of Ruminococcus gnavus, a common human gut commensal. Different approaches of introducing hydrophobic UV-active tags to lactose as well-suited sialyltransferase acceptors have been explored and a simple two-step high-yield chemical synthetic procedure has been identified. The UV-active hydrophobic tag facilitates monitoring reaction progress and allows facile product purification by C18-cartridges. A two-step enzyme-catalyzed reaction procedure has been established to combine with C18 cartridge-based purification process for high-yield production of the desired product in multigram scales with the recycled use of chromophore-tagged lactoside starting material and sialoside intermediate. This study demonstrated an environmentally friendly highly-efficient synthetic and purification strategy for the production of 2,7-anhydro-Neu5Ac to explore its potential functions.
已开发出一种唾液酸转移酶受体标记和两步酶反应策略，用于大规模化化学酶法合成 2,7-脱水-N-乙酰神经氨酸（2,7-脱水-Neu5Ac），该化合物可作为普通人类肠道共生菌 Ruminococcus gnavus 的唯一碳源。已经探索了将疏水性紫外活性标签引入乳糖作为合适的唾液酸转移酶受体的不同方法，并确定了一种简单的两步高产化学合成程序。紫外活性疏水性标签有助于监测反应进程，并允许通过 C18 筒轻松进行产物纯化。已经建立了两步酶催化反应程序，与基于 C18 筒的纯化过程相结合，以在多克规模上以高产率生产所需产物，并可回收利用带有发色团标记的乳糖起始原料和唾液酸苷中间产物。该研究展示了一种环保高效的 2,7-脱水-Neu5Ac 生产的合成和纯化策略，以探索其潜在功能。
