Oxidative dearomatisation: the key step of sorbicillinoid biosynthesis

被引：75

作者：

al Fahad, Ahmed ^{[1
]}

Abood, Amira ^{[1
,5
]}

Fisch, Katja M. ^{[1
]}

Osipow, Anna ^{[1
]}

Davison, Jack ^{[1
]}

Avramovic, Marija ^{[2
]}

Butts, Craig P. ^{[1
]}

Piel, Joern ^{[2
,3
]}

Simpson, Thomas J. ^{[1
]}

Cox, Russell J. ^{[1
,4
]}

机构：

[1] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England

[2] ETH, Inst Microbiol, CH-8093 Zurich, Switzerland

[3] Univ Bonn, Kekule Inst Organ Chem & Biochem, D-53121 Bonn, Germany

[4] Leibniz Univ Hannover, Inst Organ Chem, D-30167 Hannover, Germany

[5] Natl Res Ctr, Dokki, Egypt

来源：

CHEMICAL SCIENCE | 2014年 / 5卷 / 02期

基金：

英国工程与自然科学研究理事会; 英国生物技术与生命科学研究理事会;

关键词：

POLYKETIDE SYNTHASE GENES; TRICHODERMA SP USF-2690; PENICILLIUM-CHRYSOGENUM; VERTICILLIUM-INTERTEXTUM; ASPERGILLUS-NIDULANS; FUNGAL POLYKETIDE; GIBBERELLA-ZEAE; CLUSTER; PATHWAY; SORBICILLACTONE;

D O I：

10.1039/c3sc52911h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An FAD-dependent monooxygenase encoding gene (SorbC) was cloned from Penicillium chrysogenum E01-10/3 and expressed as a soluble protein in Escherichia coli. 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 sorbA and sorbB. The gene sorbA-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.

引用

页码：523 / 527

页数：5

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