Chemoenzymatic route to Tyrphostins involving lipase-catalyzed kinetic resolution of 1-phenylethanamine with alkyl cyanoacetates as novel acylating agents

Csuka, Pál; Boros, Zoltán; Őrfi, László; Dobos, Judit; Poppe, László; Hornyánszky, Gábor

doi:10.1016/j.tetasy.2015.04.013

Cited by 12 publications

(18 citation statements)

References 32 publications

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“…In addition, decreasing the isopropanol ratio from 2% to 1% doubled the resolution (entries 16 and 17). On the other hand, replacing ethanol with isopropanol and/or MtBE boosted the resolution tremendously (entries [11][12][13][14][15][16][17][18][19]. Notably, MtBE revealed a remarkable impact on the resolution of amines, especially when used with n-hexane on ODH column counting it is incompatible with Lux-3 column.…”

Section: R Peer Review 4 Of 12mentioning

confidence: 99%

“…Despite the wide applicability of chemical catalysis in asymmetric synthesis, biocatalysis has been introduced as a superior alternative to chemical catalysis and found plentiful applications in numerous fields particularly to make chiral building blocks for the pharmaceutical industry [13,14]. Of these building blocks, chiral amines were displayed as one of the most prominent examples where a plethora of biocatalysts have been implemented [1,[15][16][17].…”

Section: Introductionmentioning

confidence: 99%

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Enantioselective Chromatographic Separation and Lipase Catalyzed Asymmetric Resolution of Biologically Important Chiral Amines

2021

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Cyanoacetamides are vital synthons in synthetic organic chemistry. However, methods to enantiopure cyanoacetamides have not yet been well explored. In this work, the preparation of cyanoacetamide synthons RS-(1a–4a) or methoxyacetamides RS-(1b–4b) in enantiopure/enriched form was investigated. Compounds S-1, S-2, R-1b, R-1a, andR-2b were prepared in enantiopure form (ee > 99%) while compounds S-4, R-2a, and R-4a were achieved in ee 9%, 80%, and 76%, respectively. Many baselines enantioselective HPLC separations of amines 1–4, their cyanoacetamides (1a–4a), and methoxyacetamides (1b–4b) were achieved by utilizing diverse mobile-phase compositions and two cellulose-based CSPs (ODH® and LUX-3® columns). Such enantioselective HPLC separations were used to monitor the lipase-catalyzed kinetic resolution of amines RS-(1–4).

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Section: R Peer Review 4 Of 12mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Enantioselective Chromatographic Separation and Lipase Catalyzed Asymmetric Resolution of Biologically Important Chiral Amines

2021

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“…Az enantiomerek felhasználásával tírozin kináz inhibitorokat állítottunk elõ. 23 Különbözõképpen rögzített CaL B enzimet vizsgáltunk ecetsav, 2-metoxiecetsav és 2-etoxiecetsav izopropil észtereivel végzett amidálási reakciókban. Megállapítottuk, hogy az izopropil észterek minden mutatóban felülmúlják az etil észterek teljesítményét, mind szakaszos, mind folytonos eljárások esetében.…”

Section: áBra Enzimkatalizált Kinetikus Rezolválásokunclassified

A szintetikus kémiától az enzimmérnökségig – A Bioorganikus Kémiai Kutatócsoport bemutatása

Poppe¹,

Nagy²,

Hornyánszky³

2018

MKF

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“…Presumably, introduction of isopropyl as a leaving group into acylating agents diminished the non-selective chemical acylation as side-reaction with the ethyl esters, thereby increasing the apparent selectivity of the enzymatic process. In addition to the alkyl alkoxyacetates [22,23], alkyl 2-cyanoacetates proved to be effective acylating agents with CaLB as well [24].…”

Section: Introductionmentioning

confidence: 99%

“…Since our studies have demonstrated that changing ethyl esters to isopropyl esters [22][23][24] is advantageous due to diminishing the minor amount of chemical catalysis impairing the selectivity of the enzymatic process with ethyl esters, we investigated in this study the diisopropyl malonate as an acylating agent in the CaLB-catalyzed kinetic resolution of amines.…”

Section: Introductionmentioning

confidence: 99%

Diisopropyl Malonate as Acylating Agent in Kinetic Resolution of Chiral Amines with Lipase B from Candida antarctica

Szemes

Malta-Lakó

Tóth

et al. 2022

Period. Polytech. Chem. Eng.

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Activity of diisopropyl malonate (2) as a novel acylating agent was investigated in kinetic resolution (KR) of various racemic amines [(±)-1a-d] catalyzed by lipase B from Candida antarctica. Diisopropyl malonate (2) proved to be effective acylating agent with four racemic amines [(±)-2-aminoheptane, (±)-1-methoxy-2-propylamine, (±)-1-phenylethylamine and (±)-4-phenylbutan-2-amine; (±)-1a-d, respectively] selected for this study. The lipase-catalyzed acylation of the amines (±)-1a-d with 2 proceeded with good conversions (44.9–52.1%) and provided the expected (R)-amides [(R)-3a-d] in moderate to excellent yields (51–98%) with high enantiomeric excess (ee(R)-3a-d 92.0–99.9%) after 4 h reaction time under mild reaction conditions in batch mode. The best conversion (50%) combined with high enantiomeric purity (ee(R)-2d > 99%ee) was achieved in the KR from racemic 2-aminoheptane (±)-1a. The four novel (R)-amides [(R)-3a-d] were isolated and properly characterized.

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Chemoenzymatic route to Tyrphostins involving lipase-catalyzed kinetic resolution of 1-phenylethanamine with alkyl cyanoacetates as novel acylating agents

Cited by 12 publications

References 32 publications

Enantioselective Chromatographic Separation and Lipase Catalyzed Asymmetric Resolution of Biologically Important Chiral Amines

Enantioselective Chromatographic Separation and Lipase Catalyzed Asymmetric Resolution of Biologically Important Chiral Amines

A szintetikus kémiától az enzimmérnökségig – A Bioorganikus Kémiai Kutatócsoport bemutatása

Diisopropyl Malonate as Acylating Agent in Kinetic Resolution of Chiral Amines with Lipase B from Candida antarctica

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