CGS 30440: A Dual Inhibitor of Angiotensin‐Converting Enzyme and Neutral Endopeptidase 24.11

The enantioselective synthesis of α‐thiocarboxylic acids by biocatalytic dynamic kinetic resolution (DKR) of nitrile precursors exploiting nitrilase enzymes is described. A panel of 35 nitrilase biocatalysts were screened and enzymes Nit27 and Nit34 were found to catalyse the DKR of racemic α‐thionitriles under mild conditions, affording the corresponding carboxylic acids with high conversions and good‐to‐excellent ee. The ammonia produced in situ during the biocatalytic transformation favours the racemization of the nitrile enantiomers and, in turn, the DKR without the need of any external additive base.

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Enantioselective Synthesis of α‐Thiocarboxylic Acids by Nitrilase Biocatalysed Dynamic Kinetic Resolution of α‐Thionitriles

Lauder

Anselmi

Finnigan

et al. 2020

Chemistry A European J

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Synthesis of heteroaryl substituted α‐mercapto acids from thiomalic acid using hexafluoroacetone as protecting and activating reagent

Pumpor

Windeisen

Burger

2003

Journal of Heterocyclic Chem

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Asymmetric syntheses of α-mercapto carboxylic acid derivatives by dynamic resolution of N-methyl pseudoephedrine α-bromo esters

Nam¹,

Lee²,

Kim³

et al. 2002

Tetrahedron Letters

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CGS 30440: A Dual Inhibitor of Angiotensin‐Converting Enzyme and Neutral Endopeptidase 24.11

Cited by 5 publications

References 72 publications

Enantioselective Synthesis of α‐Thiocarboxylic Acids by Nitrilase Biocatalysed Dynamic Kinetic Resolution of α‐Thionitriles

Enantioselective Synthesis of α‐Thiocarboxylic Acids by Nitrilase Biocatalysed Dynamic Kinetic Resolution of α‐Thionitriles

Synthesis of heteroaryl substituted α‐mercapto acids from thiomalic acid using hexafluoroacetone as protecting and activating reagent

Asymmetric syntheses of α-mercapto carboxylic acid derivatives by dynamic resolution of N-methyl pseudoephedrine α-bromo esters

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