{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Tassano E"],"funding":["Austrian Science Fund FWF"],"pagination":["2742-2751"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC6099231"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["360(14)"],"pubmed_abstract":["The biocatalytic asymmetric disproportionation of aldehydes catalyzed by horse liver alcohol dehydrogenase (HLADH) was assessed in detail on a series of racemic 2-arylpropanals. Statistical optimization by means of design of experiments (DoE) allowed the identification of critical interdependencies between several reaction parameters and revealed a specific experimental window for reaching an 'optimal compromise' in the reaction outcome. The biocatalytic system could be applied to a variety of 2-arylpropanals and granted access in a redox-neutral manner to enantioenriched (<i>S</i>)-profens and profenols following a parallel interconnected dynamic asymmetric transformation (PIDAT). The reaction can be performed in aqueous buffer at ambient conditions, does not rely on a sacrificial co-substrate, and requires only catalytic amounts of cofactor and a single enzyme. The high atom-efficiency was exemplified by the conversion of 75 mM of <i>rac</i>-2-phenylpropanal with 0.03 mol% of HLADH in the presence of ∼0.013 eq. of oxidized nicotinamide adenine dinucleotide (NAD<sup>+</sup>), yielding 28.1 mM of (<i>S</i>)-2-phenylpropanol in 96% <i>ee</i> and 26.5 mM of (<i>S</i>)-2-phenylpropionic acid in 89% <i>ee</i>, in 73% overall conversion. Isolated yield of 62% was obtained on 100 mg-scale, with intact enantiopurities."],"journal":["Advanced synthesis & catalysis"],"pubmed_title":["Biocatalytic Parallel Interconnected Dynamic Asymmetric Disproportionation of α-Substituted Aldehydes: Atom-Efficient Access to Enantiopure (<i>S</i>)-Profens and Profenols."],"pmcid":["PMC6099231"],"funding_grant_id":["P 30519","P30519"],"pubmed_authors":["Tassano E","Hall M","Faber K"],"additional_accession":[]},"is_claimable":false,"name":"Biocatalytic Parallel Interconnected Dynamic Asymmetric Disproportionation of α-Substituted Aldehydes: Atom-Efficient Access to Enantiopure (<i>S</i>)-Profens and Profenols.","description":"The biocatalytic asymmetric disproportionation of aldehydes catalyzed by horse liver alcohol dehydrogenase (HLADH) was assessed in detail on a series of racemic 2-arylpropanals. Statistical optimization by means of design of experiments (DoE) allowed the identification of critical interdependencies between several reaction parameters and revealed a specific experimental window for reaching an 'optimal compromise' in the reaction outcome. The biocatalytic system could be applied to a variety of 2-arylpropanals and granted access in a redox-neutral manner to enantioenriched (<i>S</i>)-profens and profenols following a parallel interconnected dynamic asymmetric transformation (PIDAT). The reaction can be performed in aqueous buffer at ambient conditions, does not rely on a sacrificial co-substrate, and requires only catalytic amounts of cofactor and a single enzyme. The high atom-efficiency was exemplified by the conversion of 75 mM of <i>rac</i>-2-phenylpropanal with 0.03 mol% of HLADH in the presence of ∼0.013 eq. of oxidized nicotinamide adenine dinucleotide (NAD<sup>+</sup>), yielding 28.1 mM of (<i>S</i>)-2-phenylpropanol in 96% <i>ee</i> and 26.5 mM of (<i>S</i>)-2-phenylpropionic acid in 89% <i>ee</i>, in 73% overall conversion. Isolated yield of 62% was obtained on 100 mg-scale, with intact enantiopurities.","dates":{"release":"2018-01-01T00:00:00Z","publication":"2018 Jul","modification":"2025-04-19T06:29:48.013Z","creation":"2019-03-26T23:52:48Z"},"accession":"S-EPMC6099231","cross_references":{"pubmed":["30147639"],"doi":["10.1002/adsc.201800541"]}}