Kinetic resolution of (±)-diethyl- and dibenzyl hydroxy(phenyl)methanephosphonates and their acyl derivatives with lipases

Malinowska, B; Majewska, Paulina; Szatkowski, Paweł; Kafarski, Paweł; Lejczak, Barbara

doi:10.3109/10242422.2011.631211

Cited by 4 publications

(6 citation statements)

References 15 publications

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“…Yield: 80%; δ P (121.5 MHz, D 2 O) 19.4; δ P,lit (121.5 MHz, CDCl 3 ) 22.4; δ C (125.8 MHz, D 2 O) 70.7 (d, 1 J 158.5, PCH), 127.1 (d, 3 J 5.8, C 2 ), 128.2 (d, 4 J 3.0, C 3 ), 128.5 (d, 5 J 2.3, C 4 ), 137.1 (C 1 ); δ H (500.1 MHz, D 2 O) 4.88 (1H, d, 2 J P,H 12.3, PCH), 7.23‐7.38 (5H, m, Ar); [2M + H] + , found 377.0545. C 14 H 18 O 8 P 2 requires 377.0550.…”

Section: Methodsmentioning

confidence: 99%

“…Dimethyl and diethyl α‐hydroxyphosphonates are extensively studied compounds; however, the synthesis of the corresponding dibenzyl phosphonates has hardly been investigated, as so far only a few papers reported their synthesis . Two dibenzyl α‐hydroxyphosphonates were synthesized on the surface of Al 2 O 3 ‐KF .…”

Section: Introductionmentioning

confidence: 99%

“…Extraction with CH 2 Cl 2 afforded the products in low yields of 50%. The same method was used for the preparation of another derivative in a resolution study . In another article, not any detail on the preparation was provided.…”

Section: Introductionmentioning

confidence: 99%

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Green synthesis and cytotoxic activity of dibenzyl α‐hydroxyphosphonates and α‐hydroxyphosphonic acids

Rádai

Szeles

Kiss

et al. 2018

Heteroatom Chemistry

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A series of dibenzyl α‐hydroxyphosphonates and the corresponding α‐hydroxyphosphonic acids, mostly new compounds, have been synthesized. The dibenzyl α‐hydroxyphosphonates have been obtained in the Pudovik reaction of substituted benzaldehydes and dibenzyl phosphite in the presence of triethylamine as the catalyst. The amount of the solvent was minimized during the reaction, and the workup involved crystallization from the reaction mixture. A new protocol was developed to transform the dibenzyl 1‐hydroxyphosphonates to the corresponding phosphonic acids by catalytic hydrogenation. The derivatives prepared were screened as potential cytotoxic agents against Mes‐Sa human uterine sarcoma cell line.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Green synthesis and cytotoxic activity of dibenzyl α‐hydroxyphosphonates and α‐hydroxyphosphonic acids

Rádai

Szeles

Kiss

et al. 2018

Heteroatom Chemistry

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“…In addition, α-hydroxyphosphonate derivatives of tetrazolo [1,5-a]quinoline were found to possess antibacterial and antifungal properties (Kategaonkar et al, 2010). Our earlier studies, aimed at obtaining pure enantiomers of organophosphonic compounds, demonstrated that some hydroxyphosphonates might be delivered with good or excellent enantioselectivity by means of biotransformations (Skwarczyński et al, 1999;Malinowska et al, 2011). It was also found that analogous compounds like hydroxyphosphinates, may be produced in a similar way Majewska et al, 2009).…”

Section: Introductionmentioning

confidence: 99%

“…These microorganisms were selected from several bacterial strains stored in the Department of Bioorganic Chemistry, Wrocław University of Technology collection. The selection was made on the basis of best lipolytic activity measured by Spirit blue agar test and previously observed results for the hydrolysis of butyryloxyphosphonates Malinowska et al, 2011). Compounds 2a and 2b were also chemically synthesized as a racemic mixture of all isomers, to confirm the identity of the hydrolysis products.…”

Section: Introductionmentioning

confidence: 99%

Research paper Microbial biotransformation of two phosphonoacetic acid derivatives bearing two stereomeric centres

Szyszkowiak¹,

Majewska²

2013

bta

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Three strains of microorganisms: Bacillus subtilis, Serratia liquefaciens and Escherichia coli were tested as whole-cell biocatalysts for the kinetic resolution of isomers of two new phosphonoacetic acid derivatives. Used compounds possess two chiral centres -one at the carbon adjacent to both functional groups and the other at the phosphorus. Biocatalytic hydrolysis of 2-butyryloxy-2-(butoxyetoxyphosphinyl)acetic acid and 2-butyryloxy-2-(isobutoxyetoxyphosphinyl)acetic acid with whole cells of Bacillus subtilis produced corresponding hydroxyphosphonates with diastereoselectivity ranging from 50 to 60%.

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Chemoenzymatic Synthesis of 5‐Hydroxymethylfurfural (HMF)‐Derived Plasticizers by Coupling HMF Reduction with Enzymatic Esterification

et al. 2020

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Biobased plasticizers, as substitutes for phthalates, have been synthesized from 5‐hydroxymethylfurfural (HMF) and carboxylic acids (or esters) through a chemoenzymatic cascade process that involves as its first step the reduction of 5‐hydroxymethylfurfural into 2,5‐bis(hydroxymethyl)furan (BHMF), followed by the esterification of BHMF with carboxylic acids (or esters) by using a supported lipase (Novozym 435). The reduction of HMF into BHMF is performed by using monodisperse metallic Co nanoparticles with a thin carbon shell (Co@C) with high activity and selectivity. After optimization of reaction conditions (temperature, hydrogen pressure, and solvent), it is possible to achieve 97 % conversion of HMF with 99 % selectivity to BHMF after 2 h reaction time. The reduction of HMF and esterification of BHMF using carboxylic acids or vinyl esters as acyl donors by lipase are optimized separately in batch and in fixed‐bed continuous reactors. The coupling of two flow reactors (for reduction and subsequent esterification) working under optimized reaction conditions affords the diesters of BHMF in roughly 90 % yield with no loss of activity during 60 h of operation.

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Kinetic resolution of (±)-diethyl- and dibenzyl hydroxy(phenyl)methanephosphonates and their acyl derivatives with lipases

Cited by 4 publications

References 15 publications

Green synthesis and cytotoxic activity of dibenzyl α‐hydroxyphosphonates and α‐hydroxyphosphonic acids

Green synthesis and cytotoxic activity of dibenzyl α‐hydroxyphosphonates and α‐hydroxyphosphonic acids

Research paper Microbial biotransformation of two phosphonoacetic acid derivatives bearing two stereomeric centres

Chemoenzymatic Synthesis of 5‐Hydroxymethylfurfural (HMF)‐Derived Plasticizers by Coupling HMF Reduction with Enzymatic Esterification

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