Biotransformations of 2-hydroxy-2-(ethoxyphenylphosphinyl)acetic acid and the determination of the absolute configuration of all isomers

Majewska, Paulina

doi:10.1016/j.bioorg.2015.05.006

Cited by 10 publications

(2 citation statements)

References 14 publications

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“…Compound 1a: The procedure of synthesis of compounds 2 was carried out according to the procedure for similar compounds described previously [16,24]. To diethyl or dibutyl phosphonate (20 mmol), glyoxylic acid monohydrate (1.84 g, 20 mmol) was added, followed by the addition of triethylamine (2.79 mL, 20 mmol).…”

Section: General Procedures Of Synthesis Of Dimethyl and Dibutyl 1-carboxy-1-hydroxymethylphosphonatesmentioning

confidence: 99%

Lipase-Catalyzed Kinetic Resolution of Dimethyl and Dibutyl 1-Butyryloxy-1-carboxymethylphosphonates

Majewska

2021

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The main objective of this study is the enantioselective synthesis of carboxyhydroxyphosphonates by lipase-catalyzed reactions. For this purpose, racemic dimethyl and dibutyl 1-butyryloxy-1-carboxymethylphosphonates were synthesized and hydrolyzed, using a wide spectrum of commercially available lipases from different sources (e.g., fungi and bacteria). The best hydrolysis results of dimethyl 1-butyryloxy-1-carboxymethylphosphonate were obtained with the use of lipases from Candida rugosa, Candida antarctica, and Aspergillus niger, leading to optically active dimethyl 1-carboxy-1-hydroxymethylphosphonate (58%–98% enantiomeric excess) with high enantiomeric ratio (reaching up to 126). However, in the case of hydrolysis of dibutyl 1-butyryloxy-1-carboxymethylphosphonate, the best results were obtained by lipases from Burkholderia cepacia and Termomyces lanuginosus, leading to optically active dibutyl 1-carboxy-1-hydroxymethylphosphonate (66%–68% enantiomeric excess) with moderate enantiomeric ratio (reaching up to 8.6). The absolute configuration of the products after biotransformation was also determined. In most cases, lipases hydrolyzed (R) enantiomers of both compounds.

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Section: General Procedures Of Synthesis Of Dimethyl and Dibutyl 1-carboxy-1-hydroxymethylphosphonatesmentioning

confidence: 99%

Lipase-Catalyzed Kinetic Resolution of Dimethyl and Dibutyl 1-Butyryloxy-1-carboxymethylphosphonates

Majewska

2021

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“…[57][58][59][60]. The amide group is one of the most important structural motifs and it appears to be crucial in the functioning of living organisms [61][62][63][64][65]. Therefore, a detailed description of the conformation of systems with the amide moiety is very important.…”

Section: Equilibrium Between Intramolecular and Intermolecular Hydrogmentioning

confidence: 99%

Intramolecular Hydrogen Bonds in Selected Aromatic Compounds: Recent Developments

et al. 2019

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A review of intramolecular hydrogen bonding in ortho-hydroxyaryl Schiff bases, ortho-hydroxyaryl Mannich bases, dipyrrins, ortho-hydroxyaryl ketones, ortho-hydroxyaryl amides, and 4-Bora-3a,4a-diaza-s-indacene (BODIPY) dyes with tautomeric sensors as substituents is presented in this paper. Ortho-hydroxy Schiff and Mannich base derivatives are known as model molecules for analysing the properties of intramolecular hydrogen bonding. The compounds under discussion possess physicochemical features modulated by the presence of strong intramolecular hydrogen bonds. The equilibrium between intra-and inter-molecular hydrogen bonds in BODIPY is discussed. Therefore, the summary can serve as a knowledge compendium of the influence of the hydrogen bond on the molecular properties of aromatic compounds.

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Asymmetric Biocatalysis

2016

Asymmetric Synthesis in Organophosphorus Chemistry

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Biotransformations of 2-hydroxy-2-(ethoxyphenylphosphinyl)acetic acid and the determination of the absolute configuration of all isomers

Cited by 10 publications

References 14 publications

Lipase-Catalyzed Kinetic Resolution of Dimethyl and Dibutyl 1-Butyryloxy-1-carboxymethylphosphonates

Lipase-Catalyzed Kinetic Resolution of Dimethyl and Dibutyl 1-Butyryloxy-1-carboxymethylphosphonates

Intramolecular Hydrogen Bonds in Selected Aromatic Compounds: Recent Developments

Asymmetric Biocatalysis

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