Publications

2019

Takeichi T, Hirabayashi T, Miyasaka Y, Kawamoto A, Okuno Y, Taguchi S, Tanahashi K, Murase C, Takama H, Tanaka K, Boeglin WE, Calcutt MW, Watanabe D, Kono M, Muro Y, Ishikawa J, Ohno T, Brash AR, Akiyama M. SDR9C7 catalyzes critical dehydrogenation of acylceramides for skin barrier formation. J Clin Invest. 2019 Oct 31. [Epub ahead of print] PMCID: in process

Kornilov A, Kennedy PD, Aldrovandi M, Watson AJA, Hinz C, Harless B, Colombo J, Maxey KM, Tyrrell VJ, Simon M, Aggarwal VK, Boeglin WE, Brash AR, Murphy RC, O’Donnell VB. (2019) Revising the structure of a new eicosanoid from human platelets to 8,9-11,12-diepoxy-13-hydroxyeicosadienoic acid. J Biol Chem. 2019 294(23):9225-9238. PMCID: PMC6556573

Pakhomova S, Boeglin WE, Neau DB, Bartlett SG, Brash AR, Newcomer ME. (2019) An ensemble of lipoxygenase structures reveals novel conformations of the Fe coordination sphere. Protein Sci. 28(5):920-927. PMCID: PMC6459989

Crumrine D, Khnykin D, Krieg P, Man MQ, Celli A, Mauro TM, Wakefield JS, Menon G, Mauldin E, Miner JH, Lin MH, Brash AR, Sprecher E, Radner FPW, Choate K, Roop D, Uchida Y, Gruber R, Schmuth M, Elias PM. (2019) Perspective: Mutations in Recessive Congenital Ichthyoses Illuminate the Origin and Functions of the Corneocyte Lipid Envelope. J. Invest. Dermatol. 139(4):760-768. PMID:30471252

2018

Brash, A.R. (2018) Catalase-related allene oxide synthase, on a biosynthetic route to fatty acid cyclopentenones: expression and assay of the enzyme and preparation of the 8R-HPETE substrate. Methods Enzymol. 605: 51 – 68. PMCID: PMC6590083

Davis RW, Allweil A, Tian J, Brash AR, Sulikowski GA. (2018) Stereocontrolled synthesis of four isomeric linoleate triols of relevance to skin barrier formation and function. Tetrahedron Lett. 2018 Dec 26;59(52):4571-4573. PMCID: PMC6424341

Sorensen PW, Appelt C, Stacey NE, Goetz FW, Brash AR.(2018) High levels of circulating prostaglandin F_2α associated with ovulation stimulate female sexual receptivity and spawning behavior in the goldfish (Carassius auratus). Gen. Comp. Endocrinol. 267:128-136.

Yamanashi, H., Boeglin, W.E., Morisseau, C., Davis, R.W., Sulikowski, G.A., Hammock, B.D.,and Brash, A.R. (2018) Catalytic activities of mammalian epoxide hydrolases with cis and trans fatty acid epoxides relevant to skin barrier function. J. Lipid Res.59: 684-895. PMCID: PMC5880498

2017

Hirabayashi, T., Anjo, T., Kaneko, A., Senoo, Y., Shibata, A., Takama, H., Yokoyama, K., Nishito, Y., Ono, T., Taya, C., Muramatsu, K., Fukami, K., Muñoz-Garcia, A., Brash, A. R., Ikeda, K., Arita, M., Akiyama, M., and Murakami, M. (2017) PNPLA1 has a crucial role in skin barrier function by directing acylceramide biosynthesis. Nat. Commun. 8:14609. doi: 10.1038/ncomms14609. PMCID: PMC5937976

Teder T, Boeglin WE, Schneider C, Brash AR (2017) A fungal catalase reacts selectively with the 13S fatty acid hydroperoxide products of the adjacent lipoxygenase gene and exhibits 13S-hydroperoxide-dependent peroxidase activity. Biochim. Biophys. Acta 1862: 706-715. PMCID: PMC5481161

Teder, T., Boelgin, W.E., and Brash, A.R. (2017) Oxidation of C18 Hydroxy-Polyunsaturated Fatty Acids to Epoxide or Ketone by Catalase-Related Hemoproteins Activated with Iodosylbenzene. Lipids 52: 587-597. PMCID: PMC5551055

2016

Hebert SP, Cha JK, Brash AR, Schlegel HB. (2016) Investigation into 9(S)-HPODE-derived allene oxide to cyclopentenone cyclization mechanism via diradical oxyallyl intermediates. Org. Biomol. Chem. 2016 Apr 14;14(14):3544-57. PMCID: PMC4814336

Martin SA, Brash AR, Murphy RC. (2016) The discovery and early structural studies of arachidonic acid. J. Lipid Res. 2016 Jul;57(7):1126-32. PMCID: PMC4918860

Chiba T, Thomas CP, Calcutt MW, Boeglin WE, O’Donnell VB, Brash AR. (2016) The precise structures and stereochemistry of trihydroxy-linoleates esterified in human and porcine epidermis and their significance in skin barrier function: IMPLICATION OF AN EPOXIDE HYDROLASE IN THE TRANSFORMATIONS OF LINOLEATE. J. Biol. Chem. 291(28):14540-5. PMCID: PMC4938176

Mashhadi, Z., Newcomer ME and Brash AR (2106) The Thr-His Connection on the Distal Heme of Catalase-related Hemoproteins: a Hallmark of Reaction with Fatty Acid Hydroperoxides. ChemBioChem, 17:2000-2006. PMCID:PMC5267355

2015

Newcomer ME, Brash AR. (2015) The structural basis for specificity in lipoxygenase catalysis. Protein Sci. 24(3):298-309 PMCID:PMC4353356

Mashhadi Z, Boeglin WE, Brash AR. (2015) Robust inhibitory effects of conjugated linolenic acids on a cyclooxygenase-related linoleate 10S-dioxygenase: Comparison with COX-1 and COX-2. Biochim Biophys Acta. 2015 Oct;1851(10):1346-52. PMCID: PMC4561586

Teder T, Lõhelaid H, Boeglin WE, Calcutt WM, Brash AR, Samel N. (2015) A Catalase-related Hemoprotein in Coral Is Specialized for Synthesis of Short-chain Aldehydes: DISCOVERY OF P450-TYPE HYDROPEROXIDE LYASE ACTIVITY IN A CATALASE.

J Biol Chem. 2015 Aug 7;290(32):19823-32. PMCID: PMC4528142

2014

Brash AR, Niraula NP, Boeglin WE, Mashhadi Z. (2014) An Ancient Relative of Cyclooxygenase in Cyanobacteria Is a Linoleate 10S-Dioxygenase That Works in Tandem with a Catalase-related Protein with Specific 10S-Hydroperoxide Lyase Activity. J Biol Chem. 289(19):13101-11 PMCID: PMC4036322

Mashhadi Z, Boeglin WE, Brash AR. (2014) Inhibitory effects of a novel Val to Thr mutation on the distal heme of human catalase. Biochimie. 2014 Nov;106:180-3. PMCID: PMC4250446

Neau DB, Bender G, Boeglin WE, Bartlett SG, Brash AR, Newcomer ME. (2014) Crystal Structure of a lipoxygenase in complex with substrate: the arachidonic acid binding site of 8R-lipoxygenase. J. Biol. Chem. 289(46):31905-13 PMCID: PMC4231669

Teder T, Boeglin WE, Brash AR. (2014) Lipoxygenase-catalyzed transformation of epoxy fatty acids to hydroxy-endoperoxides: a potential P450 and lipoxygenase interaction. J Lipid Res. 55(12):2587-96. PMCID: PMC4242451

2013

Jin J., Zheng Y., Boeglin W.E., Brash A.R. (2013) Biosynthesis, Isolation, and NMR Analysis of Leukotriene A Epoxides: Substrate Chirality as a Determinant of the cis or trans Epoxide Configuration. J. Lipid Res. 54(3):754-61. PMCID: PMC3719183

Thomas, C.P., Boeglin, W.E., Garcia-Diaz, Y., O’Donnell, V.B. and Brash, A.R. (2013) Steric analysis of epoxyalcohol and trihydroxy derivatives of 9-hydroperoxy-linoleic acid from hematin and enzymatic synthesis. Chem. Phys. Lipids 167-168: 21-32. PMCID: PMC3678760

Brash, A. R., Boeglin, W. E., Stec, D. F., Voehler, M., Schneider, C., and Cha, J. K. (2013) Isolation and characterization of two geometric allene oxide isomers synthesized from 9S-hydroperoxy-linoleic acid by P450 CYP74C3: Stereochemical assignment of natural fatty acid allene oxides. J. Biol. Chem. 288: 20979-20806. PMCID: PMC3774351

Muñoz-Garcia, A., Thomas, C.P., Keeney, D.S., Zheng, Y., and Brash, A.R. (2013) Importance of the lipoxygenase-hepoxilin pathway in the mammalian epidermal barrier. Biochim. Biophys. Acta 1841(3):401-408 PMCID: PMC4116325

2012

218. Brash AR, Schneider C, Hamberg M. (2012) Applications of Stereospecifically-Labeled Fatty Acids in Oxygenase and Desaturase Biochemistry. Lipids. 47, 101-116.

PMCID: PMC3315059

Jin, J., Boeglin, W.E., Cha, J.K., Brash, A.R. (2012) 8R-Lipoxygenase-catalyzed synthesis of a prominent cis-epoxyalcohol from dihomo-γ-linolenic acid: a distinctive transformation compared with S-lipoxygenases. J Lipid Res. 2012 Feb;53(2):292-9. Epub 2011 Dec 10. PMCID: PMC3269157

Gilbert NC, Rui Z, Neau DB, Waight MT, Bartlett SG, Boeglin WE, Brash AR, Newcomer ME. (2012) Conversion of human 5-lipoxygenase to a 15-lipoxygenase by a point mutation to mimic phosphorylation at Serine-663. FASEB J. 26(8):3222-9 PMCID: PMC3405276

Boeglin, W.E., and Brash, A.R. (2012) Cytochrome P450-type hydroxylation and epoxidation in a tyrosine-liganded hemoprotein, catalase-related allene oxide synthase. J. Biol. Chem. 287: 24139-24147 PMCID: PMC3397841

2011

Liu, W., Porter, N.A., Schneider, C., Brash, A.R., Yin, H. (2011) Formation of 4-hydroxynonenal from cardiolipin oxidation: intramolecular peroxyl radical addition and decomposition. Free Rad. Biol. Med. 50(1):166-178

Gilbert, N.C., Bartlett, S.G., Waight, M.T., Neau, D.B., Boeglin, W.E., Brash, A.R., Newcomer M.E. (2011) The structure of human 5-lipoxygenase. Science 331: 217-219.

Zheng Y, Yin H, Boeglin WE, Elias PM, Crumrine D, Beier DR, Brash AR. (2011) Lipoxygenases mediate the effect of essential fatty acid in skin barrier formation: A proposed role in releasing omega-hydroxyceramide for construction of the corneocyte lipid envelope. J. Biol. Chem. 286(27):24046-56.

Brash AR, Schneider C, Hamberg M. (2011) Applications of Stereospecifically-Labeled Fatty Acids in Oxygenase and Desaturase Biochemistry. Lipids. 2011 Oct 5. [Epub ahead of print]

PMID: 21971646

Bandara DM, Sono M, Bruce GS, Brash AR, Dawson JH. (2011) Coordination modes of tyrosinate-ligated catalase-type heme enzymes: Magnetic circular dichroism studies of Plexaura homomalla allene oxide synthase, Mycobacterium avium ssp. paratuberculosis protein-2744c, and bovine liver catalase in their ferric and ferrous states. J. Inorg. Biochem. 2011 Sep 22. [Epub ahead of print] PMID: 22104301

2010

Gao, B., Boeglin, W.E., and Brash, AR (2010) Omega-3 fatty acids are oxygenated at the n-7 carbon by the lipoxygenase domain of a fusion protein in the cyanobacterium Acaryochloris marina. Biochim. Biophys. Acta 2010 Jan;1801(1):58-63. Epub 2009 Sep 25.

Zheng, Y., and Brash, A.R. (2010) Formation of a cyclopropyl epoxide via a Leukotriene A synthase-related pathway in an anaerobic reaction of soybean lipoxygenase-1 with 15S-hydroperoxyeicosatetraenoic acid: Evidence that oxygen access is a determinant of secondary reactions with fatty acid hydroperoxides. J. Biol. Chem. 285(18):13427-36.

Zheng, Y., and Brash, A. R. (2010) Dioxygenase activity of epidermal lipoxygenase-3 unveiled: Typical and atypical features of its catalytic activity with natural and synthetic polyunsaturated fatty acids. J. Biol. Chem. 285: 39866-39875

Zheng, Y., and Brash, A. R. (2010) On the role of molecular oxygen in lipoxygenase activation: comparison and contrast of epidermal lipoxygenase-3 with soybean lipoxygenase-1. J. Biol. Chem. 285(51): 39876-39887.