Preprint Article Version 1 This version is not peer-reviewed

Chemo-Enzymatic Synthesis of Synthons as Precursors for Enantiopure Clenbuterol and other β2- Agonists

Version 1 : Received: 25 October 2018 / Approved: 25 October 2018 / Online: 25 October 2018 (08:44:19 CEST)

A peer-reviewed article of this Preprint also exists.

Blindheim, F.H.; Hansen, M.B.; Evjen, S.; Zhu, W.; Jacobsen, E.E. Chemoenzymatic Synthesis of Synthes as Precursors for Enantiopure Clenbuterol and Other β2 Agonists. Catalysts 2018, 8, 516. Blindheim, F.H.; Hansen, M.B.; Evjen, S.; Zhu, W.; Jacobsen, E.E. Chemoenzymatic Synthesis of Synthes as Precursors for Enantiopure Clenbuterol and Other β2 Agonists. Catalysts 2018, 8, 516.

Journal reference: Catalysts 2018, 8, 516
DOI: 10.3390/catal8110516

Abstract

(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 NADPH as the co-factor in 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. Clenbuterol is a β2-agonist used in veterinary treatment of asthma in several countries. The drug is listed on the World Anti-doping 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, the pure enantiomers need to be studied separately. Our biocatalytic approach in order to obtain enantiopure clenbuterol should be applicable to industrial scale.

Subject Areas

(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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