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设计全细胞催化辅助合成9,11-断甾体

Designed whole-cell-catalysis-assisted synthesis of 9,11-secosterols.

作者信息

Kõllo Marek, Kasari Marje, Kasari Villu, Pehk Tõnis, Järving Ivar, Lopp Margus, Jõers Arvi, Kanger Tõnis

机构信息

Department of Chemistry and Biotechnology, School of Science, Tallinn University of Technology, Akadeemia tee 15, 12618 Tallinn, Estonia.

Institute of Technology, University of Tartu, Nooruse 1, 50104 Tartu, Estonia.

出版信息

Beilstein J Org Chem. 2021 Mar 1;17:581-588. doi: 10.3762/bjoc.17.52. eCollection 2021.

Abstract

A method for the synthesis of 9,11-secosteroids starting from the natural corticosteroid cortisol is described. There are two key steps in this approach, combining chemistry and synthetic biology. Stereo- and regioselective hydroxylation at C9 (steroid numbering) is carried out using whole-cell biocatalysis, followed by the chemical cleavage of the C-C bond of the vicinal diol. The two-step method features mild reaction conditions and completely excludes the use of toxic oxidants.

摘要

描述了一种从天然皮质类固醇皮质醇开始合成9,11-断甾体的方法。这种方法有两个关键步骤,结合了化学和合成生物学。使用全细胞生物催化在C9(甾体编号)处进行立体和区域选择性羟基化,然后对邻二醇的碳-碳键进行化学裂解。该两步法具有温和的反应条件,并且完全排除了有毒氧化剂的使用。

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