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Solvent-induced 7R-dioxygenase activity of soybean 15-lipoxygenase-1 in the formation of omega-3 DPA-derived resolvin analogs

Dobson,EP, Barrow,CJ and Adcock,JL 2014, Solvent-induced 7R-dioxygenase activity of soybean 15-lipoxygenase-1 in the formation of omega-3 DPA-derived resolvin analogs, Journal of molecular catalysis b: enzymatic, vol. 108, pp. 96-102, doi: 10.1016/j.molcatb.2014.07.007.

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Title Solvent-induced 7R-dioxygenase activity of soybean 15-lipoxygenase-1 in the formation of omega-3 DPA-derived resolvin analogs
Author(s) Dobson,EP
Barrow,CJORCID iD for Barrow,CJ orcid.org/0000-0002-2153-7267
Adcock,JLORCID iD for Adcock,JL orcid.org/0000-0002-4446-518X
Journal name Journal of molecular catalysis b: enzymatic
Volume number 108
Start page 96
End page 102
Publisher Elsevier
Place of publication London, England
Publication date 2014-10
ISSN 1381-1177
1873-3158
Keyword(s) Docosapentaenoic acid
Medium engineering
n-Alcohol
Resolvins
Soybean 15-lipoxygenase-1
Science & Technology
Life Sciences & Biomedicine
Physical Sciences
Biochemistry & Molecular Biology
Chemistry, Physical
Chemistry
DOCOSAPENTAENOIC ACID DPAN-6
DOCOSAHEXAENOIC ACID
ARACHIDONIC-ACID
ANTIINFLAMMATORY ACTIONS
POSITIONAL SPECIFICITY
DOUBLE DIOXYGENATION
LIPID MEDIATORS
LIPOXYGENASE-1
OXYGENATION
RESOLUTION
Summary The resolvin family contains important anti-inflammatory and pro-resolution compounds enzymatically derived in vivo from the polyunsaturated omega-3 fatty acids, eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA). More recently, docosapentaenoic acid (DPA) has emerged as another potentially important precursor in the biological production of resolvin compounds. In this work we have used medium engineering to develop a simple method for the controlled synthesis of two di-hydroxylated diastereomers of DPAn-3 catalyzed by soybean 15-lipoxygenase-1 (15-sLOX-1) in the presence of short chain n-alcohols, including methanol, ethanol and propan-1-ol. The complete structures of the two major products, 7S,17S-dihydroxydocosapenta-8Z,10E,13Z,15E,19Z-enoic acid (7S,17S-diHDPAn-3) and 7R,17S-dihydroxydocosapenta-8Z,10E,13Z,15E,19Z- enoic acid (7R,17S-diHDPAn-3), have been elucidated using spectroscopic analysis. The alcohol-dependent R-dioxygenase activity of soybean 15-lipoxygenase with mono-hydroperoxide intermediate substrates has also been demonstrated with other biologically relevant PUFAs, including DHA, EPA and ARA. The developed method has applications in the production of closely related isomers of naturally occurring resolvins and protectins, demonstrating the versatility of 15-sLOX-1 as a biocatalyst. © 2014 Elsevier B.V.
Language eng
DOI 10.1016/j.molcatb.2014.07.007
Indigenous content off
Field of Research 100301 Biocatalysis and Enzyme Technology
030401 Biologically Active Molecules
030108 Separation Science
Socio Economic Objective 920108 Immune System and Allergy
HERDC Research category C1 Refereed article in a scholarly journal
ERA Research output type C Journal article
Grant ID DE140100162
Copyright notice ©2014, Elsevier
Free to Read? Yes
Free to Read Start Date 2016-11-01
Use Rights Creative Commons Attribution Non-Commercial No-Derivatives licence
Persistent URL http://hdl.handle.net/10536/DRO/DU:30070049

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Every reasonable effort has been made to ensure that permission has been obtained for items included in DRO. If you believe that your rights have been infringed by this repository, please contact drosupport@deakin.edu.au.