Solvent‐Free Lipase‐Catalyzed Transesterification of Alcohols with Methyl Esters Under Vacuum‐Assisted Conditions

Sánchez‐Muñoz, Grecia Katherine; Ortega‐Rojas, Marina A.; Chavelas‐Hernández, Leticia; Razo‐Hernández, Rodrigo Said; Valdéz-Camacho, Jonathan Román; Escalante, Jaime

doi:10.1002/slct.202202643

Cited by 3 publications

(4 citation statements)

References 99 publications

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“…The influence of the alcohol nature in the lipase-catalysed esterification is a wellstudied area. In this sense, a detrimental effect of short-polar alcohols on lipases has been fully documented [82][83][84][85][86][87], mainly related to the penetration of these molecules (MeOH, EtOH) into the active site, resulting in a non-desired interaction with the catalytic histidine (His224 for CALB) [16]. Additionally, MeOH and EtOH has proven to alter the composition of the carrier (Lewatit VP OC 1600, a macroporous resin composed of methacrylic acid cross-linked with divinylbenzene) used in commercial Novozyme ® 435 [69,88], promoting aggregation (both for the native and immobilized CALB) and enzyme leaking from the support at high concentrations (higher than 15% v/v) [82].…”

Section: Effect Of the Nature Of The Alkyl Orthoformates In The Kr Of...mentioning

confidence: 98%

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On the Use of Orthoformates as an Efficient Approach to Enhance the Enzymatic Enantioselective Synthesis of (S)-Ibuprofen

et al. 2023

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In this paper, we describe the effectiveness of the combination between an organic solvent system mixture with orthoformates with different chain sizes from one to four carbon atoms. These orthoesters have been used as a “water trapper/alcohol releaser molecule” to reach a notable improvement in enantioselectivity and enantiomeric excess of our target compound, (S)-2-(4-isobutylphenyl)propanoic acid (ibuprofen eutomer), during the enzymatic kinetic resolution of rac-ibuprofen using immobilized lipase B of Candida antarctica as a biocatalyst. At the same time, one of the great problems of biocatalysis in organic media has been solved by eliminating excess water in the medium that allows the reversibility of the reaction. Following the optimization of the reaction conditions, an increase in enantiomeric excess and enantioselectivity was reached by using these acyl donors in the presence of a cosolvent.

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Section: Effect Of the Nature Of The Alkyl Orthoformates In The Kr Of...mentioning

confidence: 98%

Section: Effect Of the Nature Of The Alkyl Orthoformates In The Kr Of...mentioning

confidence: 99%

On the Use of Orthoformates as an Efficient Approach to Enhance the Enzymatic Enantioselective Synthesis of (S)-Ibuprofen

et al. 2023

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“…From a green chemistry perspective, the best solvent for reactions is no solvent [24][25][26][27][28]. The solvent-free reactions are not always achievable and the selection of another more efficient solvent becomes critical.…”

Section: Introductionmentioning

confidence: 99%

Lipase-Catalyzed Strategies for the Preparation of Enantiomeric THIQ and THβC Derivatives: Green Aspects

Orsy,

Forró

2023

Molecules

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This report reviews the most important lipase-catalyzed strategies for the preparation of pharmaceutically and chemically important tetrahydroisoquinoline and tetrahydro-β-carboline enantiomers through O-acylation of the primary hydroxy group, N-acylation of the secondary amino group, and COOEt hydrolysis of the corresponding racemic compounds with simple molecular structure, which have been reported during the last decade. A brief introduction describes the importance and synthesis of tetrahydroisoquinoline and tetrahydro-β-carboline derivatives, and it formulates the objectives of this compilation. The strategies are presented in chronological order, classified according to function of the reaction type, as kinetic and dynamic kinetic resolutions, in the main text. These reactions result in the desired products with excellent ee values. The pharmacological importance of the products together with their synthesis is given in the main text. The enzymatic hydrolysis of the hydrochloride salts as racemates of the starting amino carboxylic esters furnished the desired enantiomeric amino carboxylic acids quantitatively. The enzymatic reactions, performed in tBuOMe or H2O as usable solvents, and the transformations carried out in a continuous-flow system, indicate clear advantages, including atom economy, reproducibility, safer solvents, short reaction time, rapid heating and compression vs. shaker reactions. These features are highlighted in the main text.

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“…The most popular enzyme that carried out hydrolysis and transesterification, along with other reactions, because of its catalytic promiscuity capability [24,25], is probably Lipase B from Candida Antarctica (CAL-B). Another characteristic of CAL-B which is widely exploited by synthetic organic chemists is its capability to catalyze many kinds of organic reactions with a wide variety of substrates in different organic solvents [26][27][28][29][30][31][32][33][34]. Thus, the chemo-enzymatic resolution of the racemic mixtures catalyzed by CAL-B, through alcohol acylation or ester hydrolysis [35][36][37][38][39][40][41][42][43][44], would be a practical approach for accessing the desired chiral products.…”

Section: Introductionmentioning

confidence: 99%

Asymmetric Synthesis of trans-3-Alkoxyamino-4-Oxygenated-2-Piperidones Mediated by Transition-Metal-Free Dual C-H Oxidation and Its CAL-B-Assisted Enzymatic Resolution

et al. 2023

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A general chemo-enzymatic approach to synthesize both enantioenriched trans-3-alkoxyamino-4-oxy-2-piperidones, which are important scaffold for various naturally occurring alkaloids, is reported. To this end, a selective transition-metal-free dual C−H oxidation of piperidines mediated by the TEMPO oxoammonium cation (TEMPO+) was used, followed by enzymatic resolution of the corresponding alkoxyamino-2-piperidones with Candida antarctica lipase (CAL-B), to yield the title compounds in high enantiomeric excess (ee). The absolute configuration of both enantioenriched compounds was determined using chemical correlation and circular dichroism (CD) spectroscopy. The former method highlights the oxidative ring contraction of the trans-alkoxyamine-2-piperidone ring into its corresponding 2-pyrrolidinone.

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Solvent‐Free Lipase‐Catalyzed Transesterification of Alcohols with Methyl Esters Under Vacuum‐Assisted Conditions

Cited by 3 publications

References 99 publications

On the Use of Orthoformates as an Efficient Approach to Enhance the Enzymatic Enantioselective Synthesis of (S)-Ibuprofen

On the Use of Orthoformates as an Efficient Approach to Enhance the Enzymatic Enantioselective Synthesis of (S)-Ibuprofen

Lipase-Catalyzed Strategies for the Preparation of Enantiomeric THIQ and THβC Derivatives: Green Aspects

Asymmetric Synthesis of trans-3-Alkoxyamino-4-Oxygenated-2-Piperidones Mediated by Transition-Metal-Free Dual C-H Oxidation and Its CAL-B-Assisted Enzymatic Resolution

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