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Enzymatic synthesis of 3-deoxy-d-manno-octulosonic acid (KDO) and its application for LPS assembly
Bioorganic & Medicinal Chemistry Letters ( IF 2.5 ) Pub Date : 2016-04-21 , DOI: 10.1016/j.bmcl.2016.04.061
Liuqing Wen 1 , Yuan Zheng 1 , Tiehai Li 1 , Peng George Wang 1
Affiliation  

The studies of 3-deoxy-d-manno-octulosonic acid (KDO) have been hindered due to its limited availability. Herein, an efficient enzymatic system for the facile synthesis of KDO from easy-to-get starting materials is described. In this one-pot three-enzyme (OPME) system, d-ribulose 5-phosphate, which was prepared from d-xylose, was employed as starting materials. The reaction process involves the isomerization of d-ribulose 5-phosphate to d-arabinose 5-phosphate catalyzed by d-arabinose 5-phosphate isomerase (KdsD), the aldol condensation of d-arabinose 5-phosphate and phosphoenolpyruvate (PEP) catalyzed by KDO 8-phosphate synthetase (KdsA), and the hydrolysis of KDO-8-phosphate catalyzed by KDO 8-phosphate phosphatase (KdsC). By using this OPME system, 72% isolated yield was obtained. The obtained KDO was further transferred to lipid A by KDO transferase from Escherichia coli (WaaA).



中文翻译:

3-脱氧-d-甘露辛糖酸(KDO)的酶法合成及其在 LPS 组装中的应用

3-脱氧-d-甘露辛糖酸(KDO)的研究由于其可用性有限而受到阻碍。本文描述了一种有效的酶系统,用于从易于获得的起始材料轻松合成 KDO。在该一锅三酶(OPME)系统中,采用由d-木糖制备的d-核酮糖5-磷酸作为起始原料。反应过程包括在d-阿拉伯糖5-磷酸异构酶(KdsD)催化下,d-核酮糖5-磷酸异构化为d-阿拉伯糖5-磷酸;在d-阿拉伯糖5-磷酸异构酶(KdsD)催化下,d-阿拉伯糖5-磷酸与磷酸烯醇丙酮酸(PEP)进行羟醛缩合。 KDO 8-磷酸合成酶(KdsA),以及KDO 8-磷酸磷酸酶(KdsC)催化的KDO-8-磷酸水解。通过使用该OPME系统,获得了72%的分离产率。获得的KDO通过来自大肠杆菌(WaaA)的KDO转移酶进一步转移至脂质A。

更新日期:2016-04-21
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