Journal
ISCIENCE
Volume 24, Issue 8, Pages -Publisher
CELL PRESS
DOI: 10.1016/j.isci.2021.102883
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Funding
- National Natural Science Foundation of China [31800663, 21961048]
- Guizhou Science and Technology Department [QKHZC-2019-2579, QKHJC-2019-1467]
- National First-Rate Construction Discipline of Guizhou Province (Pharmacy) [YLXKJS-YX-04]
- Science and Technology Department of Zunyi [ZSKRPT-2020-5]
- Program for Outstanding Youth of Zunyi Medical University [17zy-001]
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A dual-enzyme cascade strategy was developed for regiodivergent and stereoselective hydroxyazidation of alkenes, leading to the synthesis of various enantiomerically pure 1,2-azidoalcohols. This approach combines the asymmetric epoxidation of alkenes and regio-selective ring opening of epoxides with azide catalyzed by styrene monooxygenase and halohydrin dehalogenase. Additionally, a one-pot chemo-enzymatic route to chiral beta-hydroxytriazoles from alkenes was achieved by combining biocatalytic cascades and Cu-catalyzed azide-alkyne cycloaddition.
Asymmetric functionalization of alkenes allows the direct synthesis of a wide range of chiral compounds. Vicinal hydroxyazidation of alkenes provides a desirable path to 1,2-azidoalcohols; however, existing methods are limited by the control of stereoselectivity and regioselectivity. Herein, we describe a dual-enzyme cascade strategy for regiodivergent and stereoselective hydroxyazidation of alkenes, affording various enantiomerically pure 1,2-azidoalcohols. The biocatalytic cascade process is designed by combining styrene monooxygenase-catalyzed asymmetric epoxidation of alkenes and halohydrin dehalogenase-catalyzed regio-selective ring opening of epoxides with azide. Additionally, a one-pot chemo-enzymatic route to chiral beta-hydroxytriazoles from alkenes is developed via combining the biocatalytic cascades and Cu-catalyzed azide-alkyne cycloaddition.
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