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Lipase-catalyzed methanolysis of triricinolein in organic solvent to produce 1,2(2,3)-diricinolein

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Lipids

Abstract

The objective of this study was to find the optimal parameters for lipase-catalyzed methanolysis of triricinolein to produce 1,2(2,3)-diricinolein. Four different immobilized lipases were tested, Candida antarctica type B (CALB), Rhizomucor miehei (RML), Pseudomonas cepacia (PCL), and Penicillium roquefortii (PRL). n-Hexane and diisopropyl ether (DIPE) were examined as reaction media at three different water activities (a w), 0.11, 0.53, and 0.97. The consumption of triricinolein and the formation of 1,2(2,3)-diricinolein, methyl ricinoleate, and ricinoleic acid were followed for up to 48 h. PRL gave the highest yield of 1,2(2,3)-diricinolein. Moreover, this lipase showed the highest specificity for the studied reaction, i.e., high selectivity for the reaction with triricinolein but low for 1,2(2,3)-diricinolein. Recoveries of 93 and 88% DAG were obtained using PRL in DIPE at a w of 0.11 and 0.53, respectively. Further, NMR studies showed that a higher purity of the 1,2(2,3)-isomer vs. the 1,3-isomer was achieved at higher a w (88% at a w=0.53), compared to lower a w (71% at a w=0.11). The DAG obtained was acylated by the DAG acyltransferase from Arabidopsis thaliana. Therefore, this enzymatic product is a useful enzyme substrate for lipid biosynthesis. Accordingly, the use of PRL in DIPE at a w 0.53 is considered optimal for the synthesis of 1,2(2,3)-diricinolein from triricinolein.

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Abbreviations

AtDGAT:

cDNA coding DGAT cloned from Arabidopsis thaliana, Columbia

a w :

water activity

CALB:

Candida antarctica type B lipase

DGAT:

DAG acyltransferase

DIPE:

dusopropyl ether

ESI-MS:

electrospray ionization MS

NP-HPLC:

normal-phase HPLC

PCL:

Pseudomonas cepacia lipase

PRL:

Penicillium roquefortii lipase

RML:

Rhizomucor miehei lipase

RRO:

sn-1,2-diricinoleoyl-sn-3-oleoyl TAG

RT-PCR:

reverse-transcriptase PCR

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Authors and Affiliations

  1. Western Regional Research Center, USDA, 800 Buchanan St., 94710, Albany, CA

    Charlotta Turner, Xiaohua He, Tasha Nguyen, Jiann-Tsyh Lin, Rosalind Y. Wong, Robert E. Lundin, Leslie Harden & Thomas McKeon

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  1. Charlotta Turner
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  2. Xiaohua He
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  3. Tasha Nguyen
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  4. Jiann-Tsyh Lin
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  5. Rosalind Y. Wong
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  6. Robert E. Lundin
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  7. Leslie Harden
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  8. Thomas McKeon
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Turner, C., He, X., Nguyen, T. et al. Lipase-catalyzed methanolysis of triricinolein in organic solvent to produce 1,2(2,3)-diricinolein. Lipids 38, 1197–1206 (2003). https://doi.org/10.1007/s11745-003-1179-5

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  • DOI: https://doi.org/10.1007/s11745-003-1179-5

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