Efficient Regioselective Synthesis of the Crotonyl Polydatin Prodrug by Thermomyces lanuginosus Lipase: a Kinetics Study in Eco-friendly 2-Methyltetrahydrofuran

Estolides are fatty acid polyesters with applications in both industry and consumer products. Recently, reports have emerged detailing lipase-catalyzed synthesis of estolides from free hydroxy fatty acids. In this paper, we describe a simple alternative enzymatic process, in which castor oil is directly converted to an estolide mixture by Candida antarctica lipase A (CALA) catalyzed transesterification. The reaction mixture is analyzed by NMR to determine the estolide number (EN) and MALDI MS to identify individual components, in addition to titration to determine the acid value (AV). Estolide trimers and tetramers (EN 2–3) were formed over 24 h in a system with 2:1 (v/v) castor oil–water. Further, utilizing different lipase specificities, addition of Thermomyces lanuginosus lipase (TLL), allowed the CALA product mixture to be cleaned up by hydrolyzing attached glycerol. In addition, a three-enzyme process is suggested, in which a simple alcohol is added and Candida antarctica lipase B (CALB) is used to esterify carboxylic acids to lower AV.

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Nanoencapsulated Lecitase Ultra and Thermomyces lanuginosus Lipase, a Comparative Structural Study

Langmuir ◽

10.1021/acs.langmuir.6b00826 ◽

2016 ◽

Vol 32 (26) ◽

pp. 6746-6756 ◽

Cited By ~ 6

Author(s):

Karen M. Gonçalves ◽

Ivaldo I. Junior ◽

Vassiliki Papadimitriou ◽

Maria Zoumpanioti ◽

Ivana C. R. Leal ◽

...

Keyword(s):

Structural Study ◽

Thermomyces Lanuginosus ◽

Thermomyces Lanuginosus Lipase ◽

Lecitase Ultra ◽

Lipase A

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Single-Molecule Study of Thermomyces lanuginosus Lipase in a Detergency Application System Reveals Diffusion Pattern Remodeling by Surfactants and Calcium

ACS Applied Materials & Interfaces ◽

10.1021/acsami.1c08809 ◽

2021 ◽

Author(s):

Matias E. Moses ◽

Philip M. Lund ◽

Søren S.-R. Bohr ◽

Josephine F. Iversen ◽

Jacob Kæstel-Hansen ◽

...

Keyword(s):

Single Molecule ◽

Thermomyces Lanuginosus ◽

Application System ◽

Thermomyces Lanuginosus Lipase ◽

Diffusion Pattern

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Promoting protein self-association in non-glycosylated Thermomyces lanuginosus lipase based on crystal lattice contacts

Biochimica et Biophysica Acta (BBA) - Proteins and Proteomics ◽

10.1016/j.bbapap.2015.09.007 ◽

2015 ◽

Vol 1854 (12) ◽

pp. 1914-1921 ◽

Cited By ~ 3

Author(s):

Jens Kvist Madsen ◽

Thomas Rebsdorf Sørensen ◽

Jørn Døvling Kaspersen ◽

Maria Berggård Silow ◽

Jesper Vind ◽

...

Keyword(s):

Crystal Lattice ◽

Thermomyces Lanuginosus ◽

Thermomyces Lanuginosus Lipase ◽

Self Association

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Production of Structured Phosphatidylcholine with High Content of Myristic Acid by Lipase-Catalyzed Acidolysis and Interesterification

Catalysts ◽

10.3390/catal8070281 ◽

2018 ◽

Vol 8 (7) ◽

pp. 281 ◽

Cited By ~ 9

Author(s):

Anna Chojnacka ◽

Witold Gładkowski

Keyword(s):

Myristic Acid ◽

Rhizomucor Miehei ◽

Egg Yolk ◽

Thermomyces Lanuginosus ◽

Molar Ratio ◽

Acyl Donor ◽

Thermomyces Lanuginosus Lipase ◽

Screening Experiments ◽

Miehei Lipase ◽

Acyl Donors

Synthesis of structured phosphatidylcholine (PC) enriched with myristic acid (MA) was conducted by acidolysis and interesterification reactions using immobilized lipases as catalysts and two acyl donors: trimyristin (TMA) isolated from ground nutmeg, and myristic acid obtained by saponification of TMA. Screening experiments indicated that the most effective biocatalyst for interesterification was Rhizomucor miehei lipase (RML), whereas for acidolysis, the most active were Thermomyces lanuginosus lipase (TLL) and RML. The effect of the molar ratio of substrates (egg-yolk PC/acyl donor), enzyme loading, and different solvent on the incorporation of MA into PC and on PC recovery was studied. The maximal incorporation of MA (44 wt%) was achieved after 48 h of RML-catalyzed interesterification in hexane using substrates molar ratio (PC/trimyristin) 1/5 and 30% enzyme load. Comparable results were obtained in toluene with 1/3 substrates molar ratio. Interesterification of PC with trimyristin resulted in significantly higher MA incorporation than acidolysis with myristic acid, particularly in the reactions catalyzed by RML.

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