Old yellow enzymes: structures and structure-guided engineering for stereocomplementary bioreduction
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MINI-REVIEW
Old yellow enzymes: structures and structure-guided engineering for stereocomplementary bioreduction Qinghua Shi 1 & Huibin Wang 2 & Junling Liu 3 & Shang Li 4 & Jiyang Guo 1 & Hengyu Li 1 & Xian Jia 5 & Hua Huo 6 & Zhendong Zheng 3 & Song You 1 & Bin Qin 4 Received: 13 May 2020 / Revised: 7 August 2020 / Accepted: 17 August 2020 # Springer-Verlag GmbH Germany, part of Springer Nature 2020
Abstract Since the first discovery of old yellow enzyme 1 (OYE1) from Saccharomyces pastorianus in 1932, biocatalytic asymmetric reduction of activated alkenes by OYEs has become a valuable reaction in organic synthesis. To access stereocomplementary C=C-bond bioreduction, the mining of novel OYEs and especially the protein engineering of existing OYEs have been performed, which successfully achieved the stereocomplementary reduction in several cases and further raise the potential of applications. In this review, we analyzed the structures, active sites, and substrate recognition of OYEs, which are the bases for their substrate specificity and stereospecificity. Sequence similarity network of OYEs superfamily was also constructed to investigate the scope of characterized OYEs. The structure-guided engineering to switch the stereoselectivity of OYEs and thus access stereocomplementary bioreduction over the last decade (2009–2020) was then reviewed and discussed, which might give new insights into the mining and engineering of related biocatalysts. Key points • The sequence similarity network of OYEs superfamily was constructed and annotated. • The structures and active sites of OYEs from different classes were compared. • “Left/right” binding mode was used to explain the stereopreferences of OYEs. • Structure-guided engineering of OYEs to switch their stereoselectivity was reviewed. Keywords Biocatalysis . Old yellow enzymes . Protein engineering . Biocatalytic reduction . Stereopreference switch
Qinghua Shi, Huibin Wang and Junling Liu contributed equally to this work. * Hua Huo [email protected]
3
Department of Oncology, General Hospital of Northern Theater Command, 83 Wenhua Road, Shenhe, Shenyang 110016, People’s Republic of China
4
Wuya College of Innovation, Shenyang Pharmaceutical University, 103 Wenhua Road, Shenhe, Shenyang 110016, People’s Republic of China
5
School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, 103 Wenhua Road, Shenhe, Shenyang 110016, People’s Republic of China
6
Department of Clinical Trials Management Agency, General Hospital of Northern Theater Command, 83 Wenhua Road, Shenhe, Shenyang 110016, People’s Republic of China
* Zhendong Zheng [email protected] * Song You [email protected] * Bin Qin [email protected] 1
School of Life Sciences and Biopharmaceutical Sciences, Shenyang Pharmaceutical University, 103 Wenhua Road, Shenhe, Shenyang 110016, People’s Republic of China
2
School of Pharmacy, Shenyang Pharmaceutical University, 103 Wenhua Road, Shenhe, Shenyang 110016, People’s Republic of China
Appl Microbiol Biotechnol
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