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The Development of Flow-through Bio-Catalyst Microreactors from Silica Micro Structured Fibers for Lipid Transformations

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Lipids

Abstract

This study demonstrates the utility of a flow-through enzyme immobilized silica microreactor for lipid transformations. A silica micro structured fiber (MSF) consisting of 168 channels of internal diameter 4–5 μm provided a large surface area for the covalent immobilization of Candida antartica lipase. The specific activity of the immobilized lipase was determined by hydrolysis of p-nitrophenyl butyrate and calculated to be 0.81 U/mg. The catalytic performance of the lipase microreactor was demonstrated by the efficient ethanolysis of canola oil. The parameters affecting the performance of the MSF microreactor, including temperature and reaction flow rate, were investigated. Characterization of the lipid products exiting the microreactor was performed by non-aqueous reversed-phased liquid chromatography (NARP-LC) with evaporative light scattering detector (ELSD) and by comprehensive two-dimensional gas chromatography (GC × GC). Under optimized conditions of 1 μL/min flow rate of 5 mg/mL trioleoylglycerol (TO) in ethanol and 50 °C reaction temperature, 2-monooleoylglycerol was the main product at >90% reaction yield. The regioselectivity of the Candida antartica lipase immobilized MSF microreactor in the presence of ethanol was found to be comparable to that obtained under conventional conditions. The ability of these reusable flow-through microreactors to regioselectively form monoacylglycerides in high yield from triacylglycerides demonstrate their potential use in small-scale lipid transformations or analytical lipids profiling.

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Abbreviations

APTES:

3-(Aminopropyl)triethoxysilane

DAG:

Diacylglycerol

DO:

Dioleoylglycerol

EE:

Ethyl oleate/C18:1 ethyl ester

ELSD:

Evaporative light scattering detector

FID:

Flame ionization detector

GC × GC:

Comprehensive two-dimensional gas chromatography

HPLC:

High performance liquid chromatography

MAG:

Monoacylglycerol

MO:

Monooleoylglycerol

MSF:

Micro structured fiber

NARP-LC:

Non-aqueous reversed-phased liquid chromatography

PCF:

Photonic crystal fibers

PDMS:

Poly-dimethylsiloxane

PMMA:

Poly(methyl-methacrylate)

pNP:

p-Nitrophenol

pNPB:

p-Nitrophenyl butyrate

SEM:

Scanning electron microscope

TAG:

Triacylglycerol

TO:

Trioleoylglycerol

U:

Unit of lipase activity

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Acknowledgments

The authors acknowledge support from an NSERC Discovery grant (Dr. Jonathan Curtis) and from Grant MacEwan University Research Scholarly Activity (Dr. Samuel Mugo). The authors would also like to acknowledge Mr Olivier Niquette (LECO Canada; Mississauga, Ontario) for the generous loan of the GC × GC/FID system, Grant MacEwan Arts and Science faculty, and Ministry of Higher Education, Malaysia for providing graduate student funding (Sabiqah Tuan Anuar). The analytical assistance and support of Dr. Yuan Yuan Zhou and Karl Aryton (Grant MacEwan University, Physical Science department) and all Lipid Chemistry Group and LiPRA members is acknowledged.

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Authors and Affiliations

  1. Lipid Chemistry Group, Department of Agricultural, Food and Nutritional Science (AFNS), University of Alberta, Edmonton, AB, T6G 2P5, Canada

    Sabiqah Tuan Anuar, Carla Villegas & Jonathan M. Curtis

  2. Department of Chemistry, Universiti Malaysia Terengganu, 21030, Terengganu, Malaysia

    Sabiqah Tuan Anuar

  3. Department of Physical Sciences (Chemistry), Grant MacEwan University, Edmonton, AB, T5J 4S2, Canada

    Samuel M. Mugo

  4. Lipid Chemistry Group and LiPRA, AFNS, University of Alberta, Edmonton, AB, T6G 2P5, Canada

    Jonathan M. Curtis

Authors
  1. Sabiqah Tuan Anuar
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  2. Carla Villegas
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  3. Samuel M. Mugo
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  4. Jonathan M. Curtis
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Corresponding author

Correspondence to Jonathan M. Curtis.

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Tuan Anuar, S., Villegas, C., Mugo, S.M. et al. The Development of Flow-through Bio-Catalyst Microreactors from Silica Micro Structured Fibers for Lipid Transformations. Lipids 46, 545–555 (2011). https://doi.org/10.1007/s11745-010-3522-0

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  • DOI: https://doi.org/10.1007/s11745-010-3522-0

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