A biocatalytic hydroxylation-enabled unified approach to C19-hydroxylated steroids

Steroidal C19-hydroxylation is pivotal to the synthesis of naturally occurring bioactive C19-OH steroids and 19-norsteroidal pharmaceuticals. However, realizing this transformation is proved to be challenging through either chemical or biological synthesis. Herein, we report a highly efficient metho...

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Published in	Nature communications Vol. 10; no. 1; pp. 3378 - 9
Main Authors	Wang, Junlin, Zhang, Yanan, Liu, Huanhuan, Shang, Yong, Zhou, Linjun, Wei, Penglin, Yin, Wen-Bing, Deng, Zixin, Qu, Xudong, Zhou, Qianghui
Format	Journal Article
Language	English
Published	London Nature Publishing Group UK 29.07.2019 Nature Publishing Group Nature Portfolio
Subjects	38/77 631/92/603 639/638/549/977 639/638/92/349/977 82/80 Androstenedione Androstenedione - chemistry Androstenedione - metabolism Biocatalysis Chemical synthesis Cloning Cortodoxone - chemistry Cortodoxone - metabolism Enzymes Fermentation Genetic engineering Humanities and Social Sciences Hydroxylation Intermediates Laboratories Models, Chemical Molecular Structure multidisciplinary Optimization Organic chemistry Pregnanes - chemistry Pregnanes - metabolism Science Science (multidisciplinary) Steroid hormones Steroids Steroids - chemical synthesis Steroids - chemistry Steroids - metabolism
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Abstract	Steroidal C19-hydroxylation is pivotal to the synthesis of naturally occurring bioactive C19-OH steroids and 19-norsteroidal pharmaceuticals. However, realizing this transformation is proved to be challenging through either chemical or biological synthesis. Herein, we report a highly efficient method to synthesize 19-OH-cortexolone in 80% efficiency at the multi-gram scale. The obtained C 19 -OH-cortexolone can be readily transformed to various synthetically useful intermediates including the industrially valuable 19-OH-androstenedione, which can serve as a basis for synthesis of C19-functionalized steroids as well as 19-nor steroidal drugs. Using this biocatalytic C19-hydroxylation method, the unified synthesis of six C19-hydroxylated pregnanes is achieved in just 4 to 9 steps. In addition, the structure of sclerosteroid B is revised on the basis of our synthesis. C19 hydroxylation is a unique feature of some bioactive steroids. Here, the authors developed a direct C19 hydroxylation approach to scalably access 19-OH-cortexolone in the host T. cucumeris and then converted the product into various pharmaceutically useful products via chemical synthesis.
AbstractList	Steroidal C19-hydroxylation is pivotal to the synthesis of naturally occurring bioactive C19-OH steroids and 19-norsteroidal pharmaceuticals. However, realizing this transformation is proved to be challenging through either chemical or biological synthesis. Herein, we report a highly efficient method to synthesize 19-OH-cortexolone in 80% efficiency at the multi-gram scale. The obtained C 19 -OH-cortexolone can be readily transformed to various synthetically useful intermediates including the industrially valuable 19-OH-androstenedione, which can serve as a basis for synthesis of C19-functionalized steroids as well as 19-nor steroidal drugs. Using this biocatalytic C19-hydroxylation method, the unified synthesis of six C19-hydroxylated pregnanes is achieved in just 4 to 9 steps. In addition, the structure of sclerosteroid B is revised on the basis of our synthesis. C19 hydroxylation is a unique feature of some bioactive steroids. Here, the authors developed a direct C19 hydroxylation approach to scalably access 19-OH-cortexolone in the host T. cucumeris and then converted the product into various pharmaceutically useful products via chemical synthesis. Steroidal C19-hydroxylation is pivotal to the synthesis of naturally occurring bioactive C19-OH steroids and 19-norsteroidal pharmaceuticals. However, realizing this transformation is proved to be challenging through either chemical or biological synthesis. Herein, we report a highly efficient method to synthesize 19-OH-cortexolone in 80% efficiency at the multi-gram scale. The obtained C 19 -OH-cortexolone can be readily transformed to various synthetically useful intermediates including the industrially valuable 19-OH-androstenedione, which can serve as a basis for synthesis of C19-functionalized steroids as well as 19-nor steroidal drugs. Using this biocatalytic C19-hydroxylation method, the unified synthesis of six C19-hydroxylated pregnanes is achieved in just 4 to 9 steps. In addition, the structure of sclerosteroid B is revised on the basis of our synthesis. Steroidal C19-hydroxylation is pivotal to the synthesis of naturally occurring bioactive C19-OH steroids and 19-norsteroidal pharmaceuticals. However, realizing this transformation is proved to be challenging through either chemical or biological synthesis. Herein, we report a highly efficient method to synthesize 19-OH-cortexolone in 80% efficiency at the multi-gram scale. The obtained C19-OH-cortexolone can be readily transformed to various synthetically useful intermediates including the industrially valuable 19-OH-androstenedione, which can serve as a basis for synthesis of C19-functionalized steroids as well as 19-nor steroidal drugs. Using this biocatalytic C19-hydroxylation method, the unified synthesis of six C19-hydroxylated pregnanes is achieved in just 4 to 9 steps. In addition, the structure of sclerosteroid B is revised on the basis of our synthesis. C19 hydroxylation is a unique feature of some bioactive steroids. Here, the authors developed a direct C19 hydroxylation approach to scalably access 19-OH-cortexolone in the host T. cucumeris and then converted the product into various pharmaceutically useful products via chemical synthesis. Steroidal C19-hydroxylation is pivotal to the synthesis of naturally occurring bioactive C19-OH steroids and 19-norsteroidal pharmaceuticals. However, realizing this transformation is proved to be challenging through either chemical or biological synthesis. Herein, we report a highly efficient method to synthesize 19-OH-cortexolone in 80% efficiency at the multi-gram scale. The obtained C19-OH-cortexolone can be readily transformed to various synthetically useful intermediates including the industrially valuable 19-OH-androstenedione, which can serve as a basis for synthesis of C19-functionalized steroids as well as 19-nor steroidal drugs. Using this biocatalytic C19-hydroxylation method, the unified synthesis of six C19-hydroxylated pregnanes is achieved in just 4 to 9 steps. In addition, the structure of sclerosteroid B is revised on the basis of our synthesis.Steroidal C19-hydroxylation is pivotal to the synthesis of naturally occurring bioactive C19-OH steroids and 19-norsteroidal pharmaceuticals. However, realizing this transformation is proved to be challenging through either chemical or biological synthesis. Herein, we report a highly efficient method to synthesize 19-OH-cortexolone in 80% efficiency at the multi-gram scale. The obtained C19-OH-cortexolone can be readily transformed to various synthetically useful intermediates including the industrially valuable 19-OH-androstenedione, which can serve as a basis for synthesis of C19-functionalized steroids as well as 19-nor steroidal drugs. Using this biocatalytic C19-hydroxylation method, the unified synthesis of six C19-hydroxylated pregnanes is achieved in just 4 to 9 steps. In addition, the structure of sclerosteroid B is revised on the basis of our synthesis. Steroidal C19-hydroxylation is pivotal to the synthesis of naturally occurring bioactive C19-OH steroids and 19-norsteroidal pharmaceuticals. However, realizing this transformation is proved to be challenging through either chemical or biological synthesis. Herein, we report a highly efficient method to synthesize 19-OH-cortexolone in 80% efficiency at the multi-gram scale. The obtained C -OH-cortexolone can be readily transformed to various synthetically useful intermediates including the industrially valuable 19-OH-androstenedione, which can serve as a basis for synthesis of C19-functionalized steroids as well as 19-nor steroidal drugs. Using this biocatalytic C19-hydroxylation method, the unified synthesis of six C19-hydroxylated pregnanes is achieved in just 4 to 9 steps. In addition, the structure of sclerosteroid B is revised on the basis of our synthesis.
ArticleNumber	3378
Author	Wang, Junlin Zhang, Yanan Qu, Xudong Shang, Yong Liu, Huanhuan Zhou, Linjun Wei, Penglin Yin, Wen-Bing Deng, Zixin Zhou, Qianghui
Author_xml	– sequence: 1 givenname: Junlin surname: Wang fullname: Wang, Junlin organization: Sauvage Center for Molecular Sciences, Engineering Research Center of Organosilicon Compounds & Materials (Ministry of Education), Institute for Advanced Studies, College of Chemistry and Molecular Sciences, Wuhan University – sequence: 2 givenname: Yanan surname: Zhang fullname: Zhang, Yanan organization: Key Laboratory of Combinatorial Biosynthesis and Drug Discovery, Ministry of Education, School of Pharmaceutical Sciences, Wuhan University – sequence: 3 givenname: Huanhuan surname: Liu fullname: Liu, Huanhuan organization: Key Laboratory of Combinatorial Biosynthesis and Drug Discovery, Ministry of Education, School of Pharmaceutical Sciences, Wuhan University – sequence: 4 givenname: Yong surname: Shang fullname: Shang, Yong organization: Sauvage Center for Molecular Sciences, Engineering Research Center of Organosilicon Compounds & Materials (Ministry of Education), Institute for Advanced Studies, College of Chemistry and Molecular Sciences, Wuhan University – sequence: 5 givenname: Linjun surname: Zhou fullname: Zhou, Linjun organization: Key Laboratory of Combinatorial Biosynthesis and Drug Discovery, Ministry of Education, School of Pharmaceutical Sciences, Wuhan University – sequence: 6 givenname: Penglin surname: Wei fullname: Wei, Penglin organization: State Key Laboratory of Mycology, Institute of Microbiology, Chinese Academy of Sciences – sequence: 7 givenname: Wen-Bing surname: Yin fullname: Yin, Wen-Bing organization: State Key Laboratory of Mycology, Institute of Microbiology, Chinese Academy of Sciences – sequence: 8 givenname: Zixin surname: Deng fullname: Deng, Zixin organization: Key Laboratory of Combinatorial Biosynthesis and Drug Discovery, Ministry of Education, School of Pharmaceutical Sciences, Wuhan University – sequence: 9 givenname: Xudong orcidid: 0000-0002-3301-8536 surname: Qu fullname: Qu, Xudong email: quxd@whu.edu.cn organization: Key Laboratory of Combinatorial Biosynthesis and Drug Discovery, Ministry of Education, School of Pharmaceutical Sciences, Wuhan University – sequence: 10 givenname: Qianghui orcidid: 0000-0002-8125-0380 surname: Zhou fullname: Zhou, Qianghui email: qhzhou@whu.edu.cn organization: Sauvage Center for Molecular Sciences, Engineering Research Center of Organosilicon Compounds & Materials (Ministry of Education), Institute for Advanced Studies, College of Chemistry and Molecular Sciences, Wuhan University
BackLink	https://www.ncbi.nlm.nih.gov/pubmed/31358750$$D View this record in MEDLINE/PubMed
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Snippet	Steroidal C19-hydroxylation is pivotal to the synthesis of naturally occurring bioactive C19-OH steroids and 19-norsteroidal pharmaceuticals. However,... C19 hydroxylation is a unique feature of some bioactive steroids. Here, the authors developed a direct C19 hydroxylation approach to scalably access...
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SubjectTerms	38/77 631/92/603 639/638/549/977 639/638/92/349/977 82/80 Androstenedione Androstenedione - chemistry Androstenedione - metabolism Biocatalysis Chemical synthesis Cloning Cortodoxone - chemistry Cortodoxone - metabolism Enzymes Fermentation Genetic engineering Humanities and Social Sciences Hydroxylation Intermediates Laboratories Models, Chemical Molecular Structure multidisciplinary Optimization Organic chemistry Pregnanes - chemistry Pregnanes - metabolism Science Science (multidisciplinary) Steroid hormones Steroids Steroids - chemical synthesis Steroids - chemistry Steroids - metabolism
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Title	A biocatalytic hydroxylation-enabled unified approach to C19-hydroxylated steroids
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