Sucrose phosphorylase: a powerful transglucosylation catalyst for synthesis of α-D-glucosides as industrial fine chemicals
Sucrose phosphorylase: a powerful transglucosylation catalyst for synthesis of α-D-glucosides as industrial fine chemicals
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DOI：
10.3109/10242420903411595
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发表时间：
2010-01-01
影响因子：
1.8
通讯作者：
Nidetzky, Bernd
中科院分区：
文献类型：
--
作者：
Goedl, Christiane;Sawangwan, Thornthan;Nidetzky, Bernd
蔗糖磷酸化酶是一种细菌转葡萄糖苷酶，催化蔗糖和磷酸盐转化为α-D-葡萄糖-1-磷酸和D-果糖。该酶利用类似糖苷水解酶的双置换机制，其中涉及具有催化活性的 P-葡萄糖基酶中间体。除了与磷酸盐反应外，葡萄糖基化蔗糖磷酸化酶还可以水解产生 α-D-葡萄糖，或者可以通过葡萄糖基转移到合适受体分子中的羟基进行分解，产生新的 α-D-葡萄糖苷产物。综述了蔗糖磷酸化酶的葡萄糖基受体特异性，重点介绍了该酶在糖苷合成中的应用。多羟基化合物如糖和糖醇通常能被有效地糖基化。芳基醇和不同的羧酸也充当酶促转葡萄糖基化的受体。天然渗透剂 2-O-(α-D-吡喃葡萄糖基)-sn-甘油 (GG) 是通过使用肠膜明串珠菌的磷酸化酶对蔗糖中的甘油进行区域选择性糖基化来制备的。最近开发了一种生产 GG 作为化妆品配方活性成分的工业方法。蔗糖磷酸化酶作为转葡糖基催化剂的一般优点在于使用蔗糖作为高能葡糖基供体以及酶对底物和产物的水解酶活性通常较弱。
Sucrose phosphorylase is a bacterial transglucosidase that catalyzes conversion of sucrose and phosphate into alpha-D-glucose-1-phosphate and D-fructose. The enzyme utilizes a glycoside hydrolase-like double displacement mechanism that involves a catalytically competent P-glucosyl enzyme intermediate. In addition to reaction with phosphate, glucosylated sucrose phosphorylase can undergo hydrolysis to yield alpha-D-glucose or it can decompose via glucosyl transfer to a hydroxy group in suitable acceptor molecules, giving new alpha-D-glucosidic products. The glucosyl acceptor specificity of sucrose phosphorylase is reviewed, focusing on applications of the enzyme in glucoside synthesis. Polyhydroxylated compounds such as sugars and sugar alcohols are often glucosylated efficiently. Aryl alcohols and different carboxylic acids also serve as acceptors for enzymatic transglucosylation. The natural osmolyte 2-O-(alpha-D-glucopyranosyl)-sn-glycerol (GG) was prepared by regioselective glucosylation of glycerol from sucrose using the phosphorylase from Leuconostoc mesenteroides. An industrial process for production of GG as active ingredient of cosmetic formulations has been recently developed. General advantages of sucrose phosphorylase as a transglucosylation catalyst lie in the use of sucrose as a high-energy glucosyl donor and the usually weak hydrolase activity of the enzyme towards substrate and product.