Click reaction-aided enzymatic kinetic resolution of secondary alcohols

2018 ◽  
Vol 3 (5) ◽  
pp. 790-798
Author(s):  
Mădălina Elena Moisă ◽  
László Poppe ◽  
Cristian Andrei Gal ◽  
László Csaba Bencze ◽  
Florin Dan Irimie ◽  
...  
Keyword(s):  
Kinetic Resolution ◽  
Click Reaction ◽  
Secondary Alcohols ◽  
Enzymatic Kinetic Resolution

A new, efficient lipase-mediated kinetic resolution–click-reaction-based procedure is presented for the production of both enantiomers of various 1-(hetero)aromatic ethanols.

Enzymatic kinetic resolution of secondary alcohols by esterification with FA under vacuum

2003 ◽  
Vol 80 (7) ◽  
pp. 659-663 ◽  
Author(s):  
Roxana Irimescu ◽  
Takao Saito ◽  
Katsuya Kato
Keyword(s):  
Kinetic Resolution ◽  
Secondary Alcohols ◽  
Enzymatic Kinetic Resolution

Enzymatic Kinetic Resolution of Secondary Alcohols Using an Ionic Anhydride Generated In Situ

ChemSusChem ◽  
2016 ◽  
Vol 10 (1) ◽  
pp. 296-302 ◽  
Author(s):  
Ângelo Rocha ◽  
Raquel Teixeira ◽  
Nuno M. T. Lourenço ◽  
Carlos A. M. Afonso
Keyword(s):  
Kinetic Resolution ◽  
Secondary Alcohols ◽  
Enzymatic Kinetic Resolution

Chromatography-Free Enzymatic Kinetic Resolution of Secondary Alcohols

Synthesis ◽  
2009 ◽  
Vol 2009 (21) ◽  
pp. 3654-3660 ◽  
Author(s):  
Andreas Pfaltz ◽  
Matthias Maywald
Keyword(s):  
Kinetic Resolution ◽  
Secondary Alcohols ◽  
Enzymatic Kinetic Resolution

scholarly journals Biocatalysis in continuous-flow mode: A case-study in the enzymatic kinetic resolution of secondary alcohols via acylation and deacylation reactions mediated by Novozym 435®

Biocatalysis ◽  
2017 ◽  
Vol 3 (1) ◽  
Author(s):  
Juliana Christina Thomas ◽  
Martha Daniela Burich ◽  
Pamela Taisline Bandeira ◽  
Alfredo Ricardo Marques de Oliveira ◽  
Leandro Piovan
Keyword(s):  
Continuous Flow ◽  
Energy Use ◽  
Kinetic Resolution ◽  
Enantiomeric Excess ◽  
Flow Mode ◽  
Enzymatic Reactions ◽  
Secondary Alcohols ◽  
Batch Mode ◽  
Enzymatic Kinetic Resolution

AbstractEnzymatic kinetic resolution reactions are a well-established way to achieve optically active compounds. When enzymatic reactions are combined to continuous-flow methodologies, other benefits are added, including reproducibility, optimized energy use, minimized waste generation, among others. In this context, we herein report a case study involving lipase-mediated transesterification by acylation and deacylation reactions of secondary alcohols/esters in batch and continuous-flow modes. Acylation reactions were performed with high values of enantiomeric excess (72 up to >99%) and enantioselectivity (E > 200) for both batch and continuous-flow modes. On the other hand, for deacylation reactions using n-butanol as nucleophile, enatiomeric excess ranged between 38 to >99% and E from 6 to >200 were observed for batch mode. For deacylation reactions in continuous-flow mode, results were disappointing, as in some cases, very low or no conversion was observed. Enantiomeric excess ranged from 16 to >99% and enantioselectivity from 5 to >200 were observed. In terms of productivity, continuous-flow mode reactions were superior in both strategies (acylation: r from 1.1 up to 18.1-fold higher, deacylation: 2.8 up to 7.4- fold higher in continuous-flow than in batch mode).

scholarly journals CALB Immobilized onto Magnetic Nanoparticles for Efficient Kinetic Resolution of Racemic Secondary Alcohols: Long-Term Stability and Reusability

Molecules ◽  
2019 ◽  
Vol 24 (3) ◽  
pp. 490 ◽  
Author(s):  
Xiu Xing ◽  
Jun-Qi Jia ◽  
Jing-Fan Zhang ◽  
Zi-Wen Zhou ◽  
Jun Li ◽  
...  
Keyword(s):  
Magnetic Nanoparticles ◽  
Magnetic Particles ◽  
Kinetic Resolution ◽  
Enantiomeric Excess ◽  
Secondary Alcohols ◽  
Optimal Conditions ◽  
Long Term Stability ◽  
Enzymatic Kinetic Resolution ◽  
Functionalized Magnetic Nanoparticles ◽  
Co Precipitation

In this study, an immobilization strategy for magnetic cross-linking enzyme aggregates of lipase B from Candida antarctica (CALB) was developed and investigated. Magnetic particles were prepared by conventional co-precipitation. The magnetic nanoparticles were modified with 3-aminopropyltriethoxysilane (APTES) to obtain surface amino-functionalized magnetic nanoparticles (APTES–Fe3O4) as immobilization materials. Glutaraldehyde was used as a crosslinker to covalently bind CALB to APTES–Fe3O4. The optimal conditions of immobilization of lipase and resolution of racemic 1-phenylethanol were investigated. Under optimal conditions, esters could be obtained with conversion of 50%, enantiomeric excess of product (eep) > 99%, enantiomeric excess of substrate (ees) > 99%, and enantiomeric ratio (E) > 1000. The magnetic CALB CLEAs were successfully used for enzymatic kinetic resolution of fifteen secondary alcohols. Compared with Novozym 435, the magnetic CALB CLEAs exhibited a better enantioselectivity for most substrates. The conversion was still greater than 49% after the magnetic CALB CLEAs had been reused 10 times in a 48 h reaction cycle; both ees and eep were close to 99%. Furthermore, there was little decrease in catalytic activity and enantioselectivity after being stored at −20 °C for 90 days.

Separation of secondary alcohols via enzymatic kinetic resolution using fatty esters as reusable acylating agents

2010 ◽  
Vol 21 (8) ◽  
pp. 952-956 ◽  
Author(s):  
Carlos M. Monteiro ◽  
Nuno M.T. Lourenço ◽  
Carlos A.M. Afonso
Keyword(s):  
Kinetic Resolution ◽  
Secondary Alcohols ◽  
Fatty Esters ◽  
Enzymatic Kinetic Resolution

ChemInform Abstract: Non-Enzymatic Kinetic Resolution of Secondary Alcohols

ChemInform ◽  
2010 ◽  
Vol 32 (51) ◽  
pp. no-no
Author(s):  
Peter Somfai
Keyword(s):  
Kinetic Resolution ◽  
Secondary Alcohols ◽  
Enzymatic Kinetic Resolution

Mechanochemical Enzymatic Kinetic Resolution of Secondary Alcohols under Ball-Milling Conditions

ChemCatChem ◽  
2016 ◽  
Vol 8 (10) ◽  
pp. 1769-1772 ◽  
Author(s):  
José G. Hernández ◽  
Marcus Frings ◽  
Carsten Bolm
Keyword(s):  
Ball Milling ◽  
Kinetic Resolution ◽  
Secondary Alcohols ◽  
Enzymatic Kinetic Resolution

Non‐Enzymatic Kinetic Resolution of Secondary Alcohols

2003 ◽  
pp. 175-181
Author(s):  
Peter Somfai
Keyword(s):  
Kinetic Resolution ◽  
Secondary Alcohols ◽  
Enzymatic Kinetic Resolution
Sign in / Sign up

Export Citation Format

Share Document