Lipase-mediated enantioselective kinetic resolution of racemic acidic drugs in non-standard organic solvents: Direct chiral liquid chromatography monitoring and accurate determination of the enantiomeric excesses

Ghanem, Ashraf; Aboul‐Enein, Mohamed Nabil; El‐Azzouny, Aida A.; El-Behairy, Mohammed Farrag

doi:10.1016/j.chroma.2009.10.080

Cited by 40 publications

(16 citation statements)

References 39 publications

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“…The biocatalytic resolution of a series of MOPE analogs were also investigated. The enantiomeric excesses of the substrate (ee s ) and the product (ee p ) as well as the conversion (C) and enantiomeric ratio (E) (also called enantioselectivity) were calculated using the equations described in the literature [11,12].…”

Section: Chiral Resolution Of Racemic Mopementioning

confidence: 99%

A Calcium-Ion-Stabilized Lipase from Pseudomonas stutzeri ZS04 and its Application in Resolution of Chiral Aryl Alcohols

Qin

Zhao

et al. 2016

Appl Biochem Biotechnol

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An extracellular organic solvent-tolerant lipase-producing bacterium was isolated from oil-contaminated soil samples and was identified taxonomically as Pseudomonas stutzeri, from which the lipase was purified and exhibited maximal activity at temperature of 50 °C and pH of 9.0. Meanwhile, the lipase was stable below or at 30 °C and over an alkaline pH range (7.5-11.0). Ca could significantly improve the lipase thermal stability which prompts a promising application in biocatalysis through convenient medium engineering. The lipase demonstrated striking features such as distinct stability to the most tested hydrophilic and hydrophobic solvents (25 %, v/v), and DMSO could activate the lipase dramatically. In the enzyme-catalyzed resolution, lipase ZS04 manifested excellent enantioselective esterification toward the (R)-1-(4-methoxyphenyl)-ethanol (MOPE), a crucial chiral intermediate in pharmaceuticals as well as in other analogs with strict substrate specificity and theoretical highest conversion yield. This strong advantage over other related schemes made lipase ZS04 a promising biocatalyst in organic synthesis and pharmaceutical applications.

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Section: Chiral Resolution Of Racemic Mopementioning

confidence: 99%

A Calcium-Ion-Stabilized Lipase from Pseudomonas stutzeri ZS04 and its Application in Resolution of Chiral Aryl Alcohols

Qin

Zhao

et al. 2016

Appl Biochem Biotechnol

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“…[21][22][23][24][25][26] The synthesis of all these pharmaceuticals was performed by means of a lipase-catalyzed kinetic resolution of corresponding racemic mixtures of alcohols (…”

Section: S 4r)-(à)-paroxetine (S)-(+)-citalopram (S)-(+)-zopiclonmentioning

confidence: 99%

Lipase‐Catalyzed Kinetic Resolution of Novel Antifungal N‐Substituted Benzimidazole Derivatives

et al. 2016

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A series of new N-substituted benzimidazole derivatives was synthesized and their antifungal activity against Candida albicans was evaluated. The chemical step included synthesis of appropriate ketones containing benzimidazole ring, reduction of ketones to the racemic alcohols, and acetylation of alcohols to the esters. All benzimidazole derivatives were obtained with satisfactory yields and in relatively short times. All synthesized compounds exhibit significant antifungal activity against Candida albicans 900028 ATCC (% cell inhibition at 0.25 μg concentration > 98%). Additionally, racemic mixtures of alcohols were separated by lipase-catalyzed kinetic resolution. In the enzymatic step a transesterification reaction was applied and the influence of a lipase type and solvent on the enantioselectivity of the reaction was studied. The most selective enzymes were Novozyme SP 435 and lipase Amano AK from Pseudomonas fluorescens (E > 100).

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“…Some enzymes are very specific to a particular reaction involving only certain substrates. The degree of specificity of an enzyme is depending on its biological role (Ghanem et al 2010). Additionally, enzymatic process offered more advantages over chemical process where the reactions are often highly enantio-and regio-selective towards the substrate (Ghanem 2007;Pollard and Woodley 2007;Patel 2002).…”

Section: Enzymatic Kinetic Resolutionmentioning

confidence: 99%

Advances in Bioprocess Technology

Ravindra¹

2015

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Lipase-mediated enantioselective kinetic resolution of racemic acidic drugs in non-standard organic solvents: Direct chiral liquid chromatography monitoring and accurate determination of the enantiomeric excesses

Cited by 40 publications

References 39 publications

A Calcium-Ion-Stabilized Lipase from Pseudomonas stutzeri ZS04 and its Application in Resolution of Chiral Aryl Alcohols

A Calcium-Ion-Stabilized Lipase from Pseudomonas stutzeri ZS04 and its Application in Resolution of Chiral Aryl Alcohols

Lipase‐Catalyzed Kinetic Resolution of Novel Antifungal N‐Substituted Benzimidazole Derivatives

Advances in Bioprocess Technology

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