Regioselective acylation of d-ribono-1,4-lactone catalyzed by lipases

Sebrão, Damianni; Sá, Marcus M.; Nascimento, Maria da Graça

doi:10.1016/j.procbio.2010.10.007

Cited by 15 publications

(6 citation statements)

References 52 publications

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“…It is well established that the activity of a lipase can be dramatically affected by the choice of the organic solvent, and good correlations between the reaction rate and the polarity of the solvent have been achieved . The solvents also influence the relative solubility of the substrates.…”

Section: Resultsmentioning

confidence: 99%

Lipophilization of phenolic acids with phytosterols by a chemoenzymatic method to improve their antioxidant activities

Wang

Hwang

Lim

2015

Euro J Lipid Sci & Tech

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In this study, a two‐step method for chemoenzymatic lipophilization of phenolic acids with phytosterols was studied. Optimal conditions for esterification involved the use of a binary solvent containing hexane and 2‐butanone (3 mL, 8:2, v/v), a relatively equal molar ratio of vinyl ester to phytosterols (0.1 mmol), and 100 U/mL of lipase from Candida rugosa at 55°C. Various phenolic acids were used, but only ten of them were successes. Their antioxidant activities were evaluated by total oxidation (TOTOX) value and thiobarbituric acid reactive substances (TBARS) value. Phytosteryl 4‐hydroxybenzoate, phytosteryl vanillate, and phytosteryl ferulate showed potential for use as food antioxidants. Practical applications: There is increasing interest in the development of antioxidants from natural sources because of the concerns about the safety of synthetic antioxidants. Lipophilization of phenolic acids was carried out to improve the hydrophobicity and change the antioxidant capacity of phenols. This study focuses on phytosterol, which is a food‐grade mixture of steroid compounds, having development and application potential as a cost effective food additive. According to our results, phytosteryl phenolates, which are defined as esters between phytosterols and phenolic acids, have the potential for use as alternative food antioxidants in the food industry. The lipophilization of phenolic acids with phytosterols was carried out via a two‐step chemoenzymatic route as the figure showed. The intermediate vinyl esters were first chemically produced and subsequently esterified with phytosterols catalyzed by lipase from Candida rugosa.

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Section: Resultsmentioning

confidence: 99%

Lipophilization of phenolic acids with phytosterols by a chemoenzymatic method to improve their antioxidant activities

Wang

Hwang

Lim

2015

Euro J Lipid Sci & Tech

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“…Here, ten policosanyl phenolates were successfully synthesized via vinyl phenolate intermediates, using Novozyme 435 as the catalyst. It is well established that the activity of a lipase can be greatly affected by the choice of organic solvent, and good correlations between the reaction rate and solvent polarity have been achieved . According to our previous work, a binary mixture of hexane and 2‐butanone (8:2, v/v), which is an unreactive and nontoxic solvent, was used as the solvent to maintain good lipase activity and reactants solubility.…”

Section: Resultsmentioning

confidence: 99%

Chemoenzymatically synthesized policosanyl phenolates as autoxidation inhibitors

Wang

Hwang

Lim

2014

Euro J Lipid Sci & Tech

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In this study, ten policosanyl phenolates were synthesized via a two‐step chemoenzymatic route. The intermediate vinyl esters were first chemically produced and subsequently esterified with policosanols catalyzed by Novozyme 435 (Candida antarctica lipase B). The conversion yields of the policosanyl phenolates were in the range of 4.20–37.14%. Their antioxidant activities were evaluated. Results showed that, compared with the corresponding phenolic acids, all synthesized policosanyl phenolates had better activities for peroxide value, but worse for 2,2'‐azinobis(3‐ethylbenzothiazoline‐6‐sulfonic acid) assay; policosanyl p‐coumarate and policosanyl 5‐phenylvalerate showed a moderate and durable inhibition effect on lipid oxidation both in a linoleic acid system and a cooked pork system. Practical applications: It is important to develop antioxidants from natural sources. The lipophilization of phenolic acids with fatty alcohols can improve the hydrophobicity and change the antioxidant capacity of phenols. This study focuses on policosanol, which is a food‐grade mixture of long‐chain aliphatic primary alcohols, having development and application potential as a cost‐effective food additive. According to our results, policosanyl phenolates, which are a new range of amphiphilic antioxidant molecules, have the potential for use as alternative food antioxidants in the food industry. The policosanyl phenolates were synthesized via a two‐step route as shown in the figure. The intermediate vinyl esters were first chemically produced and subsequently esterified with policosanols catalyzed by Novozyme 435 (Candida antarctica lipase B).

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“…An example of regioselective enzymatic acylation of a D-ribofuranosic ring was reported by Nascimento and coworkers 82 polymers. 94 Besides, enzymatic acylation of 157a,b was also studied.…”

Section: Acylations and Combination Of Acylations And Deacylationsmentioning

confidence: 94%

An update of biocatalytic selective acylation and deacylation of monosaccharides

Iribarren

Iglesias

2016

RSC Adv.

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Regioselective acylation of d-ribono-1,4-lactone catalyzed by lipases

Cited by 15 publications

References 52 publications

Lipophilization of phenolic acids with phytosterols by a chemoenzymatic method to improve their antioxidant activities

Lipophilization of phenolic acids with phytosterols by a chemoenzymatic method to improve their antioxidant activities

Chemoenzymatically synthesized policosanyl phenolates as autoxidation inhibitors

An update of biocatalytic selective acylation and deacylation of monosaccharides

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