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氧化脱芳构化:山梨醇类生物合成的关键步骤† 可获取电子补充信息(ESI):包含所有实验细节。见DOI: 10.1039/c3sc52911h 点击此处获取额外数据文件。

Oxidative dearomatisation: the key step of sorbicillinoid biosynthesis†Electronic supplementary information (ESI) available: Containing all experimental details. See DOI: 10.1039/c3sc52911hClick here for additional data file.

作者信息

Fahad Ahmed Al, Abood Amira, Fisch Katja M, Osipow Anna, Davison Jack, Avramović Marija, Butts Craig P, Piel Jörn, Simpson Thomas J, Cox Russell J

机构信息

School of Chemistry , University of Bristol , Cantock's Close , Bristol BS8 1TS , UK . Email:

Institute of Microbiology , Eidgenössische Technische Hochschule (ETH) Zürich , Wolfgang-Pauli-Str. 10 , 8093 Zürich , Switzerland.

出版信息

Chem Sci. 2014 Feb 23;5(2):523-527. doi: 10.1039/c3sc52911h. Epub 2013 Nov 26.

DOI:10.1039/c3sc52911h
PMID:25580210
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4285102/
Abstract

An FAD-dependent monooxygenase encoding gene (SorbC) was cloned from E01-10/3 and expressed as a soluble protein in . The enzyme efficiently performed the oxidative dearomatisation of sorbicillin and dihydrosorbicillin to give sorbicillinol and dihydrosorbicillinol respectively. Bioinformatic examination of the gene cluster surrounding SorbC indicated the presence of two polyketide synthase (PKS) encoding genes designated and . The gene -encodes a highly reducing iterative PKS while SorbB encodes a non-reducing iterative PKS which features a reductive release domain usually involved in the production of polyketide aldehydes. Using these observations and previously reported results from isotopic feeding experiments a new and simpler biosynthetic route to the sorbicillin class of secondary metabolites is proposed which is consistent with all reported experimental results.

摘要

从E01-10/3中克隆出一个依赖黄素腺嘌呤二核苷酸(FAD)的单加氧酶编码基因(SorbC),并在……中表达为可溶性蛋白。该酶能高效地将山梨霉素和二氢山梨霉素分别氧化脱芳构化,生成山梨霉素醇和二氢山梨霉素醇。对SorbC周围基因簇的生物信息学分析表明,存在两个聚酮合酶(PKS)编码基因,分别命名为……和……。基因……编码一种高度还原的迭代型PKS,而SorbB编码一种非还原的迭代型PKS,其特征在于具有一个通常参与聚酮醛生产的还原释放结构域。利用这些观察结果以及先前报道的同位素喂养实验结果,提出了一种新的、更简单的次生代谢产物山梨霉素类生物合成途径,该途径与所有报道的实验结果一致。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/60f8/4285102/45d3f7e07c63/c3sc52911h-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/60f8/4285102/0607f640e9a9/c3sc52911h-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/60f8/4285102/0a6a897532fd/c3sc52911h-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/60f8/4285102/c20b5b809fb6/c3sc52911h-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/60f8/4285102/45d3f7e07c63/c3sc52911h-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/60f8/4285102/0607f640e9a9/c3sc52911h-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/60f8/4285102/0a6a897532fd/c3sc52911h-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/60f8/4285102/c20b5b809fb6/c3sc52911h-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/60f8/4285102/45d3f7e07c63/c3sc52911h-s3.jpg

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