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利用互补糖基转移酶活性进行的两步从O-糖苷键到C-糖苷键的重排反应。

A two-step O- to C-glycosidic bond rearrangement using complementary glycosyltransferase activities.

作者信息

Gutmann Alexander, Krump Corinna, Bungaruang Linda, Nidetzky Bernd

机构信息

Institute of Biotechnology and Biochemical Engineering, Graz University of Technology, Petersgasse 12/1, A-8010 Graz, Austria.

出版信息

Chem Commun (Camb). 2014 May 28;50(41):5465-8. doi: 10.1039/c4cc00536h.

Abstract

An efficient 2'-O- to 3'-C-β-d-glucosidic bond rearrangement on the dihydrochalcone phloretin to convert phlorizin into nothofagin was achieved by combining complementary O-glycosyltransferase (OGT) and C-glycosyltransferase (CGT) activities in a one-pot transformation containing catalytic amounts of uridine 5'-diphosphate (UDP). Two separate enzymes or a single engineered dual-specific O/CGT were applied. Overall (quantitative) conversion occurred in two steps via intermediary UDP-glucose and phloretin.

摘要

通过在含有催化量尿苷5'-二磷酸(UDP)的一锅法转化中结合互补的O-糖基转移酶(OGT)和C-糖基转移酶(CGT)活性,实现了二氢查耳酮根皮素上高效的2'-O-至3'-C-β-D-葡萄糖苷键重排,从而将根皮苷转化为诺托非苷。使用了两种单独的酶或单一工程化的双特异性O/CGT。通过中间产物UDP-葡萄糖和根皮素,两步实现了总体(定量)转化。

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