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Open AccessFeature PaperArticle

Chemoenzymatic Synthesis of Synthons as Precursors for Enantiopure Clenbuterol and Other β2-Agonists

1
Department of Chemistry, Norwegian University of Science and Technology, 7491 Trondheim, Norway
2
Syncozymes Co., Ltd., No1199 Landian Road, Pudong New District, Shanghai 201318, China
*
Author to whom correspondence should be addressed.
Catalysts 2018, 8(11), 516; https://doi.org/10.3390/catal8110516
Received: 25 October 2018 / Revised: 30 October 2018 / Accepted: 1 November 2018 / Published: 4 November 2018
(This article belongs to the Section Biocatalysis)
Clenbuterol is a β2-agonist used in the veterinary treatment of asthma in several countries. The drug is listed on the World Antidoping Agency’s prohibited list due to its effect on increased protein synthesis in the body. However, racemic clenbuterol has recently been shown to reduce the risk of Parkinson’s disease. In order to reveal which one (or both) of the enantiomers that cause this effect, pure enantiomers need to be separately studied. (R)-1-(4-Amino-3,5-dichlorophenyl)-2-bromoethan-1-ol has been synthesised in 93% enantiomeric excess (ee) by asymmetric reduction of the corresponding ketone catalysed by a ketoreductase and nicotinamide adenine dinucleotide phosphate (NADPH) as the cofactor in dimethyl sulfoxide (DMSO). (S)-N-(2,6-Dichloro-4-(1-hydroxyethyl)phenyl)acetamide has been synthesised in >98% ee by the same system. Both synthons are potential precursors for clenbuterol enantiomers. View Full-Text
Keywords: (R)-1-(4-amino-3,5-dichlorophenyl)-2-bromoethan-1-ol; (S)-N-(2,6-dichloro-4-(1-hydroxyethyl)phenyl)acetamide; clenbuterol; ketoreductase; chiral chromatography (R)-1-(4-amino-3,5-dichlorophenyl)-2-bromoethan-1-ol; (S)-N-(2,6-dichloro-4-(1-hydroxyethyl)phenyl)acetamide; clenbuterol; ketoreductase; chiral chromatography
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MDPI and ACS Style

Blindheim, F.H.; Hansen, M.B.; Evjen, S.; Zhu, W.; Jacobsen, E.E. Chemoenzymatic Synthesis of Synthons as Precursors for Enantiopure Clenbuterol and Other β2-Agonists. Catalysts 2018, 8, 516. https://doi.org/10.3390/catal8110516

AMA Style

Blindheim FH, Hansen MB, Evjen S, Zhu W, Jacobsen EE. Chemoenzymatic Synthesis of Synthons as Precursors for Enantiopure Clenbuterol and Other β2-Agonists. Catalysts. 2018; 8(11):516. https://doi.org/10.3390/catal8110516

Chicago/Turabian Style

Blindheim, Fredrik H.; Hansen, Mari B.; Evjen, Sigvart; Zhu, Wei; Jacobsen, Elisabeth E. 2018. "Chemoenzymatic Synthesis of Synthons as Precursors for Enantiopure Clenbuterol and Other β2-Agonists" Catalysts 8, no. 11: 516. https://doi.org/10.3390/catal8110516

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