A chemoenzymatic synthesis of deoxy sugar esters involving stereoselective acetylation of hemiacetals catalyzed by CALB

Villo, Ly; Kreen, Malle; Kudryashova, Marina; Metsala, Andrus; Tamp, Sven; Lille, Ü; Pehk, Tõnis; Parve, Omar

doi:10.1016/j.molcatb.2010.09.008

Cited by 7 publications

(4 citation statements)

References 24 publications

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“…Kirk et al demonstrated the enantioselective hydrolysis of 1,2,3,4,6-penta- O -acetyl- d -glucose with lipases of microbial origin, following some previous similar findings with porcine pancreatic lipase . Similarly, Villo et al exploited the lipase-catalyzed hydrolysis of cyclic HAEs in the course of the synthesis of enantioenriched deoxypyranose esters, as well as deoxyfuranose esters. − Regarding HAEs not derived from sugars, Westermann and Krebs reported the enantioselective alcoholysis of cyclopropanone hemiacetals esters with lipases of microbial origin . Finally, Chênevert et al, taking advantage of the high stability toward acidic hydrolysis of a chloral-derived HAE (central trichloromethyl group, position R 3 in Scheme and Figure ), described the highly enantioselective lipase-catalyzed hydrolysis of this compound .…”

Section: Reactivity Of Haesmentioning

confidence: 85%

“…An alternative method of synthesis consists in the use of lipases (enzymes). − A vinyl acetate is first converted into acetaldehyde by a lipase, which cleaves and retains the acetate. The released acetaldehyde is then converted, by reaction with an alcohol, into a hemiacetal group, which is subsequently acetylated by the acetyl–lipase (Scheme ).…”

Section: Hae Synthetic Routesmentioning

confidence: 99%

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Hemiacetal Esters: Synthesis, Properties, and Applications of a Versatile Functional Group

Boucher,

Laviéville,

Ladmiral

et al. 2024

Macromolecules

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The present perspective provides an overview of the hemiacetal ester (HAE) chemical functionality and its use in organic synthesis and polymer science. The objective is to expose the high potential of the HAE functionality in both molecular and macromolecular chemistry through highlighting its rich and peculiar reactivity and describing the achievements in polymer chemistry involving this group. We present a summary of the different synthetic routes described so far to produce HAEs, whether this led to linear or cyclic compounds. We also outline the very rich and complex reactivity of the HAE functional group through a thorough description of its dissociation under a thermal or ionic stimulus, its hydrolysis/ alcoholysis susceptibility, and its ability to undergo exchange reactions. Finally, the successful use of HAEs for various applications in organic and polymer chemistry is also described, including, but not limited to, their use as protecting groups, initiators of polymerization, building blocks in polymer synthesis, or exchangeable linkages in covalent adaptable networks.

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Section: Reactivity Of Haesmentioning

confidence: 85%

Section: Hae Synthetic Routesmentioning

confidence: 99%

Hemiacetal Esters: Synthesis, Properties, and Applications of a Versatile Functional Group

Boucher,

Laviéville,

Ladmiral

et al. 2024

Macromolecules

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“…Another way of producing ester is by esterification process using enzymatic reaction (involving lipase) which generally regarded as safe and environmentally friendly as well as is more products specific. It is regarded as key step to produce pure sugar ester due to its stereoselective acelyation characters of the enzyme [4]. Lipase is an enzyme that is able to catalysing reversible reaction of disengagement of carboxyl ester bonding for monoester, diester and triester [5].…”

Section: Introductionmentioning

confidence: 99%

Comparison Study of Experimental and Simulation Temperature Data in the Esterification Process of Palm Fatty Acid Distillate (Pfad) in a Fluidised Reactor

Rahman

Yet

Kofli

2011

TJIEM

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Palm Oil Fatty Acid Distillate (PFAD) is a by-product from palm oil refinery process and normally used as ingredient of making candles, soap and others. Recently, many researchers have been carried out to diversify the utilisation of PFAD in industry. Among others is the enzimatically production of sugar ester using PFAD as substrate. However, limited kinetic and simulation data hindered the effort of large scale production. Hence, this study was executed to determine the kinetic parameters of the esterification process based on the simplified Ping-pong Bi-Bi model under the temperature range of 30°C ~ 45°C where immobilised lipase (Lipozyme 1M) was used as biocatalyst and isopropyl alcohol was used as solvent. The reaction was conducted in a cylinder resemble a fluidised reactor. Kinetic parameters derived from the experiments were used to simulate the production of sugar ester. The optimum temperature for the production of sugar ester was found to be at 40°C. The experimental results deviate slightly from the simulation results with error percentage of less than 11%. The model can be used to predict the production of sugar ester when the concentrations of the reactants are varied.

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“…Scheme 22 Lipase-catalysed preparation of the mono-and diacetylated derivatives of p-nitrophenyl a-L-arabinofuranoside(126).…”

mentioning

confidence: 99%

An update of biocatalytic selective acylation and deacylation of monosaccharides

Iribarren

Iglesias

2016

RSC Adv.

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A chemoenzymatic synthesis of deoxy sugar esters involving stereoselective acetylation of hemiacetals catalyzed by CALB

Cited by 7 publications

References 24 publications

Hemiacetal Esters: Synthesis, Properties, and Applications of a Versatile Functional Group

Hemiacetal Esters: Synthesis, Properties, and Applications of a Versatile Functional Group

Comparison Study of Experimental and Simulation Temperature Data in the Esterification Process of Palm Fatty Acid Distillate (Pfad) in a Fluidised Reactor

An update of biocatalytic selective acylation and deacylation of monosaccharides

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