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探讨 Baeyer-Villiger 单加氧酶在支化内酯作为聚酯前体的底物范围。

Exploring the Substrate Scope of Baeyer-Villiger Monooxygenases with Branched Lactones as Entry towards Polyesters.

机构信息

Maastricht University, Aachen-Maastricht Institute for Biobased Materials (AMIBM), Brightlands Chemelot Campus, Urmonderbaan 22, 6167 RD, Geleen, The Netherlands.

Molecular Enzymology Group, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands.

出版信息

Chembiochem. 2018 Feb 16;19(4):354-360. doi: 10.1002/cbic.201700427. Epub 2017 Nov 29.

DOI:10.1002/cbic.201700427
PMID:29078017
Abstract

Baeyer-Villiger monooxygenases (BVMOs) are biocatalysts that are able to convert cyclic ketones into lactones by the insertion of oxygen. The aim of this study was to explore the substrate scope of several BVMOs with (biobased) cyclic ketones as precursors for the synthesis of branched polyesters. The product structure and the degree of conversion of several biotransformations were determined after conversions by using self-sufficient BVMOs. Full regioselectivity towards the normal lactones of jasmatone and menthone was observed, whereas the oxidation of other substrates such as α,β-thujone and 3,3,5-trimethylcyclohexanone resulted in mixtures of regioisomers. This exploration of the substrate scope of both established and newly discovered BVMOs towards biobased ketones contributes to the development of branched polyesters from renewable resources.

摘要

Baeyer-Villiger 单加氧酶(BVMOs)是一类能够通过插入氧原子将环状酮转化为内酯的生物催化剂。本研究旨在探索几种 BVMO 对(生物基)环状酮作为合成支化聚酯前体的底物范围。通过使用自给自足的 BVMO 进行转化后,确定了几种生物转化的产物结构和转化率。观察到茉莉酮和薄荷酮的正常内酯具有完全的区域选择性,而其他底物如α,β-蒎烯和 3,3,5-三甲基环己酮的氧化则导致区域异构体的混合物。对已建立和新发现的 BVMO 对生物基酮的底物范围的探索有助于从可再生资源中开发支化聚酯。

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Toward Upscaled Biocatalytic Preparation of Lactone Building Blocks for Polymer Applications.迈向用于聚合物应用的内酯结构单元的大规模生物催化制备
Org Process Res Dev. 2018 Jul 20;22(7):803-812. doi: 10.1021/acs.oprd.8b00079. Epub 2018 Jun 12.
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Application of a thermostable Baeyer-Villiger monooxygenase for the synthesis of branched polyester precursors.
一种热稳定的拜耳-维利格单加氧酶在支链聚酯前体合成中的应用。
J Chem Technol Biotechnol. 2018 Aug;93(8):2131-2140. doi: 10.1002/jctb.5623. Epub 2018 Apr 16.