An efficient new enzymatic method for the preparation of β-aryl-β-amino acid enantiomers

Tasnádi, Gábor; Forró, Enikő; Fülöp, Ferenc

doi:10.1016/j.tetasy.2008.08.009

Cited by 31 publications

(21 citation statements)

References 28 publications

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“…It is worth noting that Tasnádi et al 18 did not find any activity of CALB (Lipolase) toward racemic ethyl 3-amino-3-phenylpropanoate, which suggests the crucial role of the benzyl protecting group in the CALB-catalyzed hydrolysis of (±)-2, (±)-8, and (±)-16.…”

Section: Resultsmentioning

confidence: 97%

Structural features of N-benzylated-β-amino acid methyl esters essential for enantiodifferentiation by lipase B from Candida antarctica in hydrolytic reactions

Rangel

Carrillo-Morales

Galindo

et al. 2015

Tetrahedron: Asymmetry

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Section: Resultsmentioning

confidence: 97%

Structural features of N-benzylated-β-amino acid methyl esters essential for enantiodifferentiation by lipase B from Candida antarctica in hydrolytic reactions

Rangel

Carrillo-Morales

Galindo

et al. 2015

Tetrahedron: Asymmetry

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“…Thus, biocatalytic paths are a promising alternative for the preparation of chiral β-amino acids. For example, the application of aminomutases ), Baeyer-Villiger monooxygenases (Rehdorf et al 2010), or lipases (Tasnádi et al 2008) is described. In the majority of cases, hydrolytic enzymes are applied for the resolution of racemic mixtures of β-amino acids or their derivatives.…”

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confidence: 99%

Stereoselective hydrolysis of aryl-substituted dihydropyrimidines by hydantoinases

Engel

Syldatk

Rudat

2011

Appl Microbiol Biotechnol

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In this study, we investigated the possibility of using a modified hydantoinase process for the production of optically pure β-amino acids. Two aryl-substituted dihydropyrimidines D,L-6-phenyl-5,6-dihydrouracil (PheDU) and para-chloro-D,L-6-phenyl-5,6-dihydrouracil (pClPheDU) were synthesized. Hydrolysis of these novel substrates to the corresponding N-carbamoyl-β-amino acids by three recombinant D-hydantoinases and several bacterial strains was tested. All applied recombinant D-hydantoinases and eight bacterial isolates catalyzed the conversion of PheDU to N-carbamoyl-β-phenylalanine (NCβPhe). Some of these biocatalysts showed an enantioselectivity for either the D- or the L-PheDU enantiomer. The second dihydropyrimidinase substrate pClPheDU was hydrolyzed by all three recombinant D-hydantoinases and six of the wild-type strains. To our knowledge, this is the first dihydropyrimidinase activity reported with this aryl-substituted dihydropyrimidine. For selected biocatalysts, hydantoinase activity towards aryl-substituted hydantoins was demonstrated as well. However, none of the bacterial strains tested so far exhibited any carbamoylase activity towards NCβPhe.

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“…In contrast, our approach used the racemic ester rac- 12 of β-phenylalanine, easily accessible in a Knoevenagel-type condensation of benzaldehyde 11 , ammonium acetate and malonic acid, followed by esterification (Scheme 1) [20–21]. A kinetic resolution of the enantiomers was achieved by enzymatic hydrolysis with Amano lipase PS from Burkholderia cepacia [22–23], a method already optimized for technical use [24]. The best results were obtained with methyl tert- butyl ether as a cosolvent [24].…”

Section: Resultsmentioning

confidence: 99%

A chiral analog of the bicyclic guanidine TBD: synthesis, structure and Brønsted base catalysis

Goldberg¹,

Sartakov²,

Bats³

et al. 2016

Beilstein J. Org. Chem.

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SummaryStarting from (S)-β-phenylalanine, easily accessible by lipase-catalyzed kinetic resolution, a chiral triamine was assembled by a reductive amination and finally cyclized to form the title compound 10. In the crystals of the guanidinium benzoate salt the six membered rings of 10 adopt conformations close to an envelope with the phenyl substituents in pseudo-axial positions. The unprotonated guanidine 10 catalyzes Diels–Alder reactions of anthrones and maleimides (25–30% ee). It also promotes as a strong Brønsted base the retro-aldol reaction of some cycloadducts with kinetic resolution of the enantiomers. In three cases, the retro-aldol products (48–83% ee) could be recrystallized to high enantiopurity (≥95% ee). The absolute configuration of several compounds is supported by anomalous X-ray diffraction and by chemical correlation.

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An efficient new enzymatic method for the preparation of β-aryl-β-amino acid enantiomers

Cited by 31 publications

References 28 publications

Structural features of N-benzylated-β-amino acid methyl esters essential for enantiodifferentiation by lipase B from Candida antarctica in hydrolytic reactions

Structural features of N-benzylated-β-amino acid methyl esters essential for enantiodifferentiation by lipase B from Candida antarctica in hydrolytic reactions

Stereoselective hydrolysis of aryl-substituted dihydropyrimidines by hydantoinases

A chiral analog of the bicyclic guanidine TBD: synthesis, structure and Brønsted base catalysis

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