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Efficient Synthesis of New Fluorinated ?-Amino Acid Enantiomers through Lipase-Catalyzed Hydrolysis.

ABSTRACT: An efficient and novel enzymatic method has been developed for the synthesis of ?-fluorophenyl-substituted ?-amino acid enantiomers through lipase PSIM (Burkholderia cepasia) catalyzed hydrolysis of racemic ?-amino carboxylic ester hydrochloride salts 3a-e in iPr₂O at 45 °C in the presence of Et₃N and H₂O. Adequate analytical methods were developed for the enantio-separation of racemic ?-amino carboxylic ester hydrochlorides 3a-e and ?-amino acids 2a-e. Preparative-scale resolutions furnished unreacted amino esters (R)-4a-e and product amino acids (S)-5a-e with excellent ee values (?99%) and good chemical yields (>48%).

SUBMITTER: Shahmohammadi S

PROVIDER: S-EPMC7766834 | biostudies-literature | 2020 Dec

REPOSITORIES: biostudies-literature

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Efficient Synthesis of New Fluorinated β-Amino Acid Enantiomers through Lipase-Catalyzed Hydrolysis.

Shahmohammadi Sayeh S Fülöp Ferenc F Forró Enikő E

Molecules (Basel, Switzerland) 20201217 24

An efficient and novel enzymatic method has been developed for the synthesis of β-fluorophenyl-substituted β-amino acid enantiomers through lipase PSIM (Burkholderia cepasia) catalyzed hydrolysis of racemic β-amino carboxylic ester hydrochloride salts 3a-e in iPr2O at 45 °C in the presence of Et3N and H2O. Adequate analytical methods were developed for the enantio-separation of racemic β-amino carboxylic ester hydrochlorides 3a- ...[more]

PMID: 33348842

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Project description:An enzymatic route for phosphorous-carbon bond formation was developed by discovering new promiscuous activity of lipase. We reported a new metal-free biocatalytic method for the synthesis of pharmacologically relevant β-phosphonomalononitriles via a lipase-catalyzed one-pot Knoevenagel-phospha-Michael reaction. We carefully analyzed the best conditions for the given reaction: the type of enzyme, temperature, and type of solvent. A series of target compounds was synthesized, with yields ranging from 43% to 93% by enzymatic reaction with Candida cylindracea (CcL) lipase as recyclable and, a few times, reusable catalyst. The advantages of this protocol are excellent yields, mild reaction conditions, low costs, and sustainability. The applicability of the same catalyst in the synthesis of β-phosphononitriles is also described. Further, the obtained compounds were validated as new potential antimicrobial agents with characteristic E. coli bacterial strains. The pivotal role of such a group of phosphonate derivatives on inhibitory activity against selected pathogenic E. coli strains was revealed. The observed results are especially important in the case of the increasing resistance of bacteria to various drugs and antibiotics. The impact of the β-phosphono malonate chemical structure on antimicrobial activity was demonstrated. The crucial role of the substituents attached to the aromatic ring on the inhibitory action against selected pathogenic E. coli strains was revealed. Among tested compounds, four β-phosphonate derivatives showed an antimicrobial activity profile similar to that obtained with currently used antibiotics such as ciprofloxacin, bleomycin, and cloxacillin. In addition, the obtained compounds constitute a convenient platform for further chemical functionalization, allowing for a convenient change in their biological activity profile. It should also be noted that the cost of the compounds obtained is low, which may be an attractive alternative to the currently used antimicrobial agents. The observed results are especially important because of the increasing resistance of bacteria to various drugs and antibiotics.

Dataset Information

Efficient Synthesis of New Fluorinated ?-Amino Acid Enantiomers through Lipase-Catalyzed Hydrolysis.

Publications

Efficient Synthesis of New Fluorinated β-Amino Acid Enantiomers through Lipase-Catalyzed Hydrolysis.

Similar Datasets

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