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Biosynthetic access to the rare antiarose sugar via an unusual reductase-epimerase
Chemical Science ( IF 8.4 ) Pub Date : 2020-03-27 , DOI: 10.1039/c9sc05766h
Yijun Yan 1, 2, 3, 4, 5 , Jing Yang 1, 2, 3, 4, 5 , Li Wang 1, 2, 3, 4, 5 , Dongdong Xu 1, 2, 3, 4, 5 , Zhiyin Yu 1, 2, 3, 4, 5 , Xiaowei Guo 1, 2, 3, 4, 5 , Geoff P. Horsman 6, 7, 8, 9 , Shuangjun Lin 10, 11, 12, 13, 14 , Meifeng Tao 10, 11, 12, 13, 14 , Sheng-Xiong Huang 1, 2, 3, 4, 5
Affiliation  

Rubrolones, isatropolones, and rubterolones are recently isolated glycosylated tropolonids with notable biological activity. They share similar aglycone skeletons but differ in their sugar moieties, and rubterolones in particular have a rare deoxysugar antiarose of unknown biosynthetic provenance. During our previously reported biosynthetic elucidation of the tropolone ring and pyridine moiety, gene inactivation experiments revealed that RubS3 is involved in sugar moiety biosynthesis. Here we report the in vitro characterization of RubS3 as a bifunctional reductase/epimerase catalyzing the formation of TDP-D-antiarose by epimerization at C3 and reduction at C4 of the key intermediate TDP-4-keto-6-deoxy-D-glucose. These new findings not only explain the biosynthetic pathway of deoxysugars in rubrolone-like natural products, but also introduce RubS3 as a new family of reductase/epimerase enzymes with potential to supply the rare antiarose unit for expanding the chemical space of glycosylated natural products.

中文翻译:

通过异常的还原酶-表观异构酶生物合成稀有的抗琼脂糖

Rubrolones,isatropolones和rubterolones是最近分离的具有显着生物学活性的糖基化的类风湿生物。它们具有相似的糖苷配基骨架,但糖部分不同,尤其是马齿rub酮具有罕见的生物合成来源未知的脱氧糖抗蔗糖酯。在我们先前报道的麦草酮环和吡啶部分的生物合成过程中,基因失活实验表明RubS3参与糖部分的生物合成。在这里,我们报告RubS3作为双功能还原酶/差向异构酶的体外表征,通过在C3上的差向异构化和在C4上还原关键中间体TDP-4-keto-6-deoxy- D来催化TDP- D- antiarose的形成。-葡萄糖。这些新发现不仅解释了类风果素样天然产物中脱氧糖的生物合成途径,而且将RubS3引入了一个新的还原酶/表观异构酶家族,有可能提供稀有的抗蔗糖单元来扩大糖基化天然产物的化学空间。
更新日期:2020-04-24
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