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

Autor:	Wei Zhu, Sigvart Evjen, Mari Bergan Hansen, Fredrik Heen Blindheim, Elisabeth Egholm Jacobsen
Rok vydání:	2018
Předmět:	Stereochemistry lcsh:Chemical technology 010402 general chemistry 01 natural sciences Catalysis clenbuterol lcsh:Chemistry Kromatografiske metoder chemistry.chemical_compound medicine lcsh:TP1-1185 Physical and Theoretical Chemistry Enantiomeric excess ketoreductase 010405 organic chemistry Enantioselective synthesis Asymmetrisk syntese Asymmetric synthesis Chromatographic methods (R)-1-(4-amino-3 5-dichlorophenyl)-2-bromoethan-1-ol Organic chemistry: 441 [VDP] Biokatalyse 0104 chemical sciences Chiral column chromatography Enantiopure drug lcsh:QD1-999 chemistry (S)-N-(2 6-dichloro-4-(1-hydroxyethyl)phenyl)acetamide Biocatalysis Clenbuterol Organisk kjemi: 441 [VDP] Enantiomer chiral chromatography Nicotinamide adenine dinucleotide phosphate medicine.drug
Zdroj:	Catalysts, Vol 8, Iss 11, p 516 (2018) Catalysts Volume 8 Issue 11
ISSN:	2073-4344
DOI:	10.3390/catal8110516
Popis:	Clenbuterol is a &beta 2-agonist used in the veterinary treatment of asthma in several countries. The drug is listed on the World Antidoping Agency&rsquo 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&rsquo 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.
Databáze:	OpenAIRE
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