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. Attached Files Name Description MIMEType Size Downloads dobson-solventinduced-accepted-2014.pdf Accepted version application/pdf 860.80KB 4 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,CJ orcid.org/0000-0002-2153-7267 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 Persistent URL http://hdl.handle.net/10536/DRO/DU:30070049 Document type: Journal Article Collections: Faculty of Science, Engineering and Built Environment School of Life and Environmental Sciences Open Access Collection Centre for Biotechnology, Chemistry and Systems Biology Related Links Link Description Connect to published version Go to link with your DU access privileges     Unless expressly stated otherwise, the copyright for items in DRO is owned by the author, with all rights reserved. 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. Versions Version Filter Type Wed, 25 Feb 2015, 16:28:06 EST Wed, 25 Feb 2015, 16:28:43 EST Thu, 26 Feb 2015, 04:03:26 EST Thu, 26 Feb 2015, 05:09:15 EST Thu, 05 Mar 2015, 14:28:15 EST Thu, 05 Mar 2015, 14:28:56 EST Tue, 16 Mar 2021, 14:33:39 EST Fri, 19 Mar 2021, 09:14:00 EST Filtered Full Citation counts:   Cited 3 times in TR Web of Science Cited 3 times in Scopus Search Google Scholar Access Statistics: 692 Abstract Views, 6 File Downloads  -  Detailed Statistics Created: Wed, 25 Feb 2015, 16:28:43 EST

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