Enantio-conversion and -selectivity of racemic atenolol kinetic resolution using free Pseudomonas fluorescens lipase (Amano) conducted via transesterification reaction

RSC Advances ◽  
2016 ◽  
Vol 6 (31) ◽  
pp. 26077-26085 ◽  
Author(s):  
Joni Agustian ◽  
Azlina Harun Kamaruddin ◽  
Hassan Y. Aboul-Enein
Keyword(s):  
Pseudomonas Fluorescens ◽  
Kinetic Resolution ◽  
Enantiomeric Purity ◽  
Transesterification Reaction ◽  
Reaction Parameters ◽  
Pharmacologically Active

Effects of reaction parameters on kinetic resolution of racemic atenolol usingPseudomonas fluorescenslipase were investigatedviatransesterification for production of pharmacologically active eutomer (S)-atenolol with high enantiomeric purity.

Exploration of the expeditious potential of Pseudomonas fluorescens lipase in the kinetic resolution of racemic intermediates and its validation through molecular docking

Chirality ◽  
2017 ◽  
Vol 30 (1) ◽  
pp. 85-94 ◽  
Author(s):  
Surbhi Soni ◽  
Bharat P. Dwivedee ◽  
Vishnu K. Sharma ◽  
Gopal Patel ◽  
Uttam C. Banerjee
Keyword(s):  
Molecular Docking ◽  
Pseudomonas Fluorescens ◽  
Kinetic Resolution

scholarly journals Determination of Transesterification Reaction Parameters Giving the Lowest Viscosity Waste Cooking Oil Biodiesel

2015 ◽  
Vol 195 ◽  
pp. 2492-2500 ◽  
Author(s):  
Atilla Bilgin ◽  
Mert Gülüm ◽  
İhsan Koyuncuoglu ◽  
Elif Nac ◽  
Abdülvahap Cakmak
Keyword(s):  
Waste Cooking Oil ◽  
Transesterification Reaction ◽  
Reaction Parameters ◽  
Cooking Oil

Immobilization to improve the properties of Pseudomonas fluorescens lipase for the kinetic resolution of 3-aryl-3-hydroxy esters

2012 ◽  
Vol 47 (1) ◽  
pp. 119-126 ◽  
Author(s):  
Jürgen Brem ◽  
Mihaela C. Turcu ◽  
Csaba Paizs ◽  
Katri Lundell ◽  
Monica-Ioana Toşa ◽  
...  
Keyword(s):  
Pseudomonas Fluorescens ◽  
Kinetic Resolution ◽  
Hydroxy Esters

scholarly journals Development of dynamic kinetic resolution on large scale for (±)-1-phenylethylamine

2010 ◽  
Vol 6 ◽  
pp. 823-829 ◽  
Author(s):  
Lisa K Thalén ◽  
Jan-E Bäckvall
Keyword(s):  
Good Yield ◽  
Large Scale ◽  
Kinetic Resolution ◽  
Catalyst Loading ◽  
Acyl Donor ◽  
Dynamic Kinetic Resolution ◽  
Reaction Parameters ◽  
Ru Catalyst ◽  
Isopropyl Acetate ◽  
Acyl Donors

Candida antarctica lipase B (CALB) and racemization catalyst 4 were combined in the dynamic kinetic resolution (DKR) of (±)-1-phenylethylamine (1). Several reaction parameters have been investigated to modify the method for application on multigram scale. A comparison of isopropyl acetate and alkyl methoxyacetates as acyl donors was carried out. It was found that lower catalyst loadings could be used to obtain (R)-2-methoxy-N-(1-phenylethyl)acetamide (3) in good yield and high ee when alkyl methoxyacetates were used as acyl donors compared to when isopropyl acetate was used as the acyl donor. The catalyst loading could be decreased to 1.25 mol % Ru-catalyst 4 and 10 mg CALB per mmol 1 when alkyl methoxyacetates were used as the acyl donor.

scholarly journals Kinetic resolution of 2-hydroxymethyl-1,4-benzodioxanes by Pseudomonas fluorescens

ARKIVOC ◽  
2008 ◽  
Vol 2008 (3) ◽  
pp. 200-210 ◽  
Author(s):  
Krisztina Kónya ◽  
Renáta Ferenczi ◽  
Andrea Czompa ◽  
Attila Kiss-Szikszai ◽  
Tibor Kurtán ◽  
...  
Keyword(s):  
Pseudomonas Fluorescens ◽  
Kinetic Resolution

scholarly journals Biocatalytic synthesis of (S)-Practolol, a selective β-blocker

Biocatalysis ◽  
2016 ◽  
Vol 1 (1) ◽  
Author(s):  
Sachin Mulik ◽  
Saptarshi Ghosh ◽  
Jayeeta Bhaumik ◽  
Uttam C. Banerjee
Keyword(s):  
Adrenergic Receptor ◽  
Kinetic Resolution ◽  
Sol Gel ◽  
Enantiomeric Excess ◽  
Green Technology ◽  
Chemoenzymatic Synthesis ◽  
Acyl Donor ◽  
Pseudomonas Cepacia ◽  
Reaction Parameters ◽  
Β Blocker

AbstractThe present study describes an efficient chemoenzymatic synthesis of enantiopure (S)-Practolol, a selective β-adrenergic receptor blocker. Prior to the synthesis of the target, a synthetic protocol for (RS)-N-4-(3-chloro-2-hydroxypropoxy)phenylacetamide, an essential precursor, was developed. Various commercial lipases were screened for the kinetic resolution of (RS)- N-4-(3-chloro-2-hydroxypropoxy)phenylacetamide using toluene as solvent and vinyl acetate as an acyl donor. Among various lipases screened, Pseudomonas cepacia sol-gel AK showed the highest enantioselectivity (96% enantiomeric excess with 50% conversion), affording (S)-1-(4-acetamidophenoxy)-3-chloropropan-2-yl acetate. Optimization of the reaction parameters was carried out in order to find the best-suited conditions for the biocatalysis. Furthermore, the enantiopure intermediate was hydrolyzed and the resulting product was reacted with isopropylamine to afford (S)-Practolol. This biocatalytic procedure depicts a green technology for the synthesis of (S)-Practolol with better yield and enantiomeric excess.

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