Biomedical Research Education & Training
Faculty Member

Porter, Ned Allen, Ph.D.
Research Professor of Chemistry
Professor of Biochemistry

Lab Url: http://www.vanderbilt.edu/AnS/Chemistry/PorterGroup/nap.html

Phone Number:

Email Address: n.porter@vanderbilt.edu

Porter, Ned's picture
Academic history
B. S. Ch. E., Princeton University
Ph. D., Harvard University

Office Address   Mailing Address

Stevenson Center 7962

VU Station B 351822


Research Keywords
Mechanistic and synthetic organic chemistry, Free Radicals and Lipid Peroxidation,Biochemistry,Spectroscopy,Toxicology

Research Specialty
Organic and Bio-Organic Chemistry

Research Description
.Most of our research has centered on the study of free radical reactions. Areas of interest include: Mechanism of the free radical reactions of natural products such as lipids and phospholipids with molecular oxygen; mechanism and utility of free radical reactions in the construction of new substructures; and the control of stereochemistry in free radical additions, including polymerization, reactions in aggregates, such as micelles and membrane bilayers, and enzyme photoactivation.

Publications
Furse, KE, Pratt, DA, Porter, NA, Lybrand, TP. Molecular Dynamics Simulations of Arachidonic Acid Complexes with COX-1 and COX-2: Insights into Equilibrium Behavior. Biochemistry, 45(10), 3189-205, 2006 PMCID:2504530

Furse, KE, Pratt, DA, Schneider, C, Brash, AR, Porter, NA, Lybrand, TP. Molecular Dynamics Simulations of Arachidonic Acid-Derived Pentadienyl Radical Intermediate Complexes with COX-1 and COX-2: Insights into Oxygenation Regio- and Stereoselectivity. Biochemistry, 45(10), 3206-18, 2006 PMCID:2504531

Kim, HY, Pratt, DA, Seal, JR, Wijtmans, M, Porter, NA. Lipid-soluble 3-pyridinol antioxidants spare alpha-tocopherol and do not efficiently mediate peroxidation of cholesterol esters in human low-density lipoprotein. J Med Chem, 48(22), 6787-9, 2005

Milne, GL, Seal, JR, Havrilla, CM, Wijtmans, M, Porter, NA. Identification and analysis of products formed from phospholipids in the free radical oxidation of human low density lipoproteins. J Lipid Res, 46(2), 307-19, 2005

Norris, JL, Hangauer, MJ, Porter, NA, Caprioli, RM. Nonacid cleavable detergents applied to MALDI mass spectrometry profiling of whole cells. J Mass Spectrom, 40(10), 1319-26, 2005

Norris, JL, Porter, NA, Caprioli, RM. Combination detergent/MALDI matrix: functional cleavable detergents for mass spectrometry. Anal Chem, 77(15), 5036-40, 2005

Schneider, C, Boeglin, WE, Yin, H, Ste, DF, Hachey, DL, Porter, NA, Brash, AR. Synthesis of dihydroperoxides of linoleic and linolenic acids and studies on their transformation to 4-hydroperoxynonenal. Lipids, 40(11), 1155-62, 2005

Yin, H, Musiek, ES, Gao, L, Porter, NA, Morrow, JD. Regiochemistry of neuroprostanes generated from the peroxidation of docosahexaenoic acid in vitro and in vivo. J Biol Chem, 280(28), 26600-11, 2005

Yin, H, Porter, NA. New insights regarding the autoxidation of polyunsaturated fatty acids. Antioxid Redox Signal, 7(1-2), 170-84, 2005

Yin, H, Porter, NA, Morrow, JD. Separation and identification of F2-isoprostane regioisomers and diastereomers by novel liquid chromatographic/mass spectrometric methods. J Chromatogr B Analyt Technol Biomed Life Sci, 827(1), 157-64, 2005

Masterson, DS, Porter, NA. Mechanism of beta-silyl diacyl peroxide decomposition: a mild and stereoselective synthesis of beta-silyl esters. J Org Chem, 69(11), 3693-9, 2004

Masterson, DS, Yin, H, Chacon, A, Hachey, DL, Norris, JL, Porter, NA. Lysine peroxycarbamates: free radical-promoted peptide cleavage. J Am Chem Soc, 126(3), 720-1, 2004

Musiek, Erik S, Cha, Jin K, Yin, Huiyong, Zackert, William E, Terry, Erin S, Porter, Ned A, Montine, Thomas J, Morrow, Jason D. Quantification of F-ring isoprostane-like compounds (F(4)-neuroprostanes) derived from docosahexaenoic acid in vivo in humans by a stable isotope dilution mass spectrometric assay. J Chromatogr B Analyt Technol Biomed Life Sci, 799(1), 95-102, 2004

Schneider, C, Porter, NA, Brash, AR. Autoxidative transformation of chiral omega6 hydroxy linoleic and arachidonic acids to chiral 4-hydroxy-2E-nonenal. Chem Res Toxicol, 17(7), 937-41, 2004

Seal, JR, Porter, NA. Liquid chromatography coordination ion-spray mass spectrometry (LC-CIS-MS) of docosahexaenoate ester hydroperoxides. Anal Bioanal Chem, 380(2), 356, 2004

Tallman, KA, Roschek, B, Porter, NA. Factors influencing the autoxidation of fatty acids: effect of olefin geometry of the nonconjugated diene. J Am Chem Soc, 126(30), 9240-7, 2004

Wijtmans, M, Pratt, DA, Brinkhorst, J, Serwa, R, Valgimigli, L, Pedulli, GF, Porter, NA. Synthesis and reactivity of some 6-substituted-2,4-dimethyl-3-pyridinols, a novel class of chain-breaking antioxidants. J Org Chem, 69(26), 9215-23, 2004

Gao, Ling, Zackert, William E, Hasford, Justin J, Danekis, Michael E, Milne, Ginger L, Remmert, Catha, Reese, Jeff, Yin, Huiyong, Tai, Hsin-Hsiung, Dey, Sudhansu K, Porter, Ned A, Morrow, Jason D. Formation of prostaglandins E2 and D2 via the isoprostane pathway: a mechanism for the generation of bioactive prostoglandins independent of cyclooxygenase. J Biol Chem, 278(31), 28479-89, 2003

Montine, Thomas J, Montine, Kathleen S, Reich, Erin E, Terry, Erin S, Porter, Ned A, Morrow, Jason D. Antioxidants significantly affect the formation of different classes of isoprostanes and neuroprostanes in rat cerebral synaptosomes. Biochem Pharmacol, 65(4), 611-7, 2003

Norris, Jeremy L, Porter, Ned A, Caprioli, Richard M. Mass spectrometry of intracellular and membrane proteins using cleavable detergents. Anal Chem, 75(23), 6642-7, 2003

Pratt, Derek A, Mills, Jeremy H, Porter, Ned A. Theoretical calculations of carbon-oxygen bond dissociation enthalpies of peroxyl radicals formed in the autoxidation of lipids. J Am Chem Soc, 125(19), 5801-10, 2003

Pratt, Derek A, Porter, Ned A. Role of hyperconjugation in determining carbon-oxygen bond dissociation enthalpies in alkylperoxyl radicals. Org Lett, 5(4), 387-90, 2003

Seal, Jennifer R, Havrilla, Christine M, Porter, Ned A, Hachey, David L. Analysis of unsaturated compounds by Ag+ coordination ionspray mass spectrometry: studies of the formation of the Ag+/lipid complex. J Am Soc Mass Spectrom, 14(8), 872-80, 2003

Seal, Jennifer R., Porter, Ned A.. Liquid chromatography coordination ion-spray mass spectrometry (LC-CIS-MS) of docosahexaenoate ester hydroperoxides. Anal Bioanal Chem, 2003

Truong, Thy T, Marriott, Philip J, Porter, Nichola A, Leeming, Rhys. Application of comprehensive two-dimensional gas chromatography to the quantification of overlapping faecal sterols. J Chromatogr A, 1019(1-2), 197-210, 2003

Wijtmans, Maikel, Pratt, Derek A., Valgimigli, Luca, DiLabio, Gino A., Pedulli, Gian Franco, Porter, Ned A.. 6-Amino-3-Pyridinols: Towards Diffusion-Controlled Chain-Breaking Antioxidants. Angew Chem Int Ed Engl, 42(36), 4370-4373, 2003

Wijtmans, Maikel, Pratt, Derek A., Valgimigli, Luca, DiLabio, Gino A., Pedulli, Gian Franco, Porter, Ned A.. 6-Amino-3-Pyridinols: Towards Diffusion-Controlled Chain-Breaking Antioxidants. Angew Chem Int Ed Engl, 42(40), 4847, 2003

Yin, H, Havrilla, CM, Gao, L, Morrow, JD, Porter, NA. Mechanisms for the formation of isoprostane endoperoxides from arachidonic acid. "Dioxetane" intermediate versus beta-fragmentation of peroxyl radicals. J Biol Chem, 278(19), 16720-5, 2003

Yin, Huiyong, Morrow, Jason D., Porter, Ned A.. Identification of a novel class of endoperoxides from Arachidonate autoxidation. J Biol Chem, 2003

Yin, Huiyong, Porter, Ned A. Specificity of the ferrous oxidation of xylenol orange assay: analysis of autoxidation products of cholesteryl arachidonate. Anal Biochem, 313(2), 319-26, 2003

Culbertson, Sean M, Antunes, Fernando, Havrilla, Christine M, Milne, Ginger L, Porter, Ned A. Determination of the alpha-tocopherol inhibition rate constant for peroxidation in low-density lipoprotein. Chem Res Toxicol, 15(6), 870-6, 2002

Fam, Samuel S, Murphey, Laine J, Terry, Erin S, Zackert, William E, Chen, Yan, Gao, Ling, Pandalai, Saurabh, Milne, Ginger L, Roberts, L Jackson, Porter, Ned A, Montine, Thomas J, Morrow, Jason D. Formation of highly reactive A-ring and J-ring isoprostane-like compounds (A4/J4-neuroprostanes) in vivo from docosahexaenoic acid. J Biol Chem, 277(39), 36076-84, 2002

Feng, Hao, Kavrakova, Ivanka K, Pratt, Derek A, Tellinghuisen, Joel, Porter, Ned A. Lewis acid-promoted Kharasch-Curran additions: a competition kinetics study of bromine atom transfer addition of N-alpha-bromoacetyl-oxazolidinone to 1-hexene. J Org Chem, 67(17), 6050-4, 2002

Fessel, Joshua P, Porter, Ned A, Moore, Kevin P, Sheller, James R, Roberts, L Jackson. Discovery of lipid peroxidation products formed in vivo with a substituted tetrahydrofuran ring (isofurans) that are favored by increased oxygen tension. Proc Natl Acad Sci U S A, 99(26), 16713-8, 2002 PMCID:139209

Huiyong Yin, Christine M. Havrilla, Jason D. Morrow and Ned A. Porter. Formation of Isoprostane Bicylic Endoperoxides from the Autoxidation of Cholesteryl Arachidonate. J. Amer. Chem. Soc., 124, 7745-7754, 2002

Masterson, Douglas S, Porter, Ned A. Diastereoselective free radical halogenation, azidation, and rearrangement of beta-silyl Barton esters. Org Lett, 4(24), 4253-6, 2002

Thuring, Jan Willem, Li, Hui, Porter, Ned A. Comparative study of the active site caging of serine proteases: thrombin and factor Xa. Biochemistry, 41(6), 2002-13, 2002

Yin, Huiyong, Havrilla, Christine M, Morrow, Jason D, Porter, Ned A. Formation of isoprostane bicyclic endoperoxides from the autoxidation of cholesteryl arachidonate. J Am Chem Soc, 124(26), 7745-54, 2002

Claus Schneider, Keri A. Tallman, Ned A. Porter, and Alan R. Brash. Two distinct pathways of formation of 4-hydroxy-nonenal . Mechanisms of non-enzymatic transformation of the 9- and 13-hydroperoxides of linoleic acid to 4-hydroxy-alkenals . J. Biol. Chem., 276, 20831-20838, 2001

Culbertson, S M, Vinqvist, M R, Barclay, L R, Porter, N A. Minimizing tocopherol-mediated radical phase transfer in low-density lipoprotein oxidation with an amphiphilic unsymmetrical azo initiator. J Am Chem Soc, 123(37), 8951-60, 2001

Culbertson, Sean M., Porter, Ned A.. Design of Unsymmetrical Azo Initiators to Increase Radical Generation Efficiency in Low-Density Lipoproteins. Free Radic Res, 33(6), 705-718, 2001

Milne, G L, Porter, N A. Separation and identification of phospholipid peroxidation products. Lipids, 36(11), 1265-75, 2001

Schneider, C, Tallman, K A, Porter, N A, Brash, A R. Two distinct pathways of formation of 4-hydroxynonenal. Mechanisms of nonenzymatic transformation of the 9- and 13-hydroperoxides of linoleic acid to 4-hydroxyalkenals. J Biol Chem, 276(24), 20831-8, 2001

Tallman, K A, Pratt, D A, Porter, N A. Kinetic products of linoleate peroxidation: rapid beta-fragmentation of nonconjugated peroxyls. J Am Chem Soc, 123(47), 11827-8, 2001

Truong, T T, Marriott, P J, Porter, N A. Analytical study of comprehensive and targeted multidimensional gas chromatography incorporating modulated cryogenic trapping. J AOAC Int, 84(2), 323-35, 2001

Yin, H, Hachey, D L, Porter, N A. Analysis of diacyl peroxides by Ag+ coordination ionspray tandem mass spectrometry: free radical pathways of complex decomposition. J Am Soc Mass Spectrom, 12(4), 449-55, 2001

Christine M. Havrilla, David L. Hachey, and Ned A. Porter. Coordination (Ag+) Ion Spray-Mass Spectrometry of Peroxidation Products of Cholesterol Linoleate and Cholesterol Arachidonate: High-Performance Liquid Chromatography-Mass Spectrometry Analysis of Peroxide Products from Polyunsaturated Lipid Autoxidation. J. Amer. Chem. Soc, 122, 8042-8055, 2000

Culbertson, S M, Porter, N A. Design of unsymmetrical azo initiators to increase radical generation efficiency in low-density lipoproteins. Free Radic Res, 33(6), 705-18, 2000

Pollastri, M P, Porter, N A, McIntosh, T J, Simon, S A. Synthesis, structure, and thermal properties of 1,2-dipalmitoylgalloylglycerol (DPGG), a novel self-adhering lipid. Chem Phys Lipids, 104(1), 67-74, 2000

S. M. Culbertson and N. A. Porter. The Initiation of Radical Reactions in Molecular Aggregates and Lipoproteins. Free Radical Research, 33(6), 705-718, 2000

Yin, H, Hachey, D L, Porter, N A. Structural analysis of diacyl peroxides by electrospray tandem mass spectrometry with ammonium acetate: bond homolysis of peroxide-ammonium and peroxide-proton adducts. Rapid Commun Mass Spectrom, 14(14), 1248-54, 2000

McIntosh, T J, Pollastri, M P, Porter, N A, Simon, S A. Polyphenols increase adhesion between lipid bilayers by forming interbilayer bridges. Basic Life Sci, 66, 451-70, 1999

Arroyo, J G, Jones, P B, Porter, N A, Hatchell, D L. In vivo photoactivation of caged-thrombin. Thromb Haemost, 78(2), 791-3, 1997

Porter, N A, Bush, K A, Kinter, K S. Photo-reversible binding of thrombin to avidin by means of a photolabile inhibitor. J Photochem Photobiol B, 38(1), 61-9, 1997

Huh, N W, Porter, N A, McIntosh, T J, Simon, S A. The interaction of polyphenols with bilayers: conditions for increasing bilayer adhesion. Biophys J, 71(6), 3261-77, 1996 PMCID:1233814

Kenar, J A, Havrilla, C M, Porter, N A, Guyton, J R, Brown, S A, Klemp, K F, Selinger, E. Identification and quantification of regioisomeric cholesteryl linoleate hydroperoxides in oxidized human low density lipoprotein and high density lipoprotein. Chem Res Toxicol, 9(4), 737-44, 1996

Porter, N A, Caldwell, S E, Mills, K A. Mechanisms of free radical oxidation of unsaturated lipids. Lipids, 30(4), 277-90, 1995

Porter, N A, Bruhnke, J D. Photocoagulation of human plasma: acyl serine proteinase photochemistry. Photochem Photobiol, 51(1), 37-43, 1990

Porter, N A, Dussault, P, Breyer, R A, Kaplan, J, Morelli, J. The resolution of racemic hydroperoxides: a chromatography-based separation of perketals derived from arachidonic, linoleic, and oleic acid hydroperoxides. Chem Res Toxicol, 3(3), 236-43, 1990

Pryor, W A, Porter, N A. Suggested mechanisms for the production of 4-hydroxy-2-nonenal from the autoxidation of polyunsaturated fatty acids. Free Radic Biol Med, 8(6), 541-3, 1990

Wagner, C R, Porter, N A. A phospholipase C protocol for phospholipid peroxidation analysis. Chem Res Toxicol, 1(5), 274-80, 1988

Pizzo, S V, Turner, A D, Gonias, S L, Monroe, D M, Roberts, H R, Porter, N A. Nontoxic irreversible inhibitors of factors IXa, Xa, and thrombin: potential therapeutic agents for the in vivo regulation of thrombin generation and activity. Ann N Y Acad Sci, 485, 199-203, 1986

Pizzo, S V, Turner, A D, Porter, N A, Gonias, S L. Evaluation of p-amidinophenyl esters as potential antithrombotic agents. Thromb Haemost, 56(3), 387-90, 1986

Turner, A D, Monroe, D M, Roberts, H R, Porter, N A, Pizzo, S V. p-Amidino esters as irreversible inhibitors of factors IXa and Xa and thrombin. Biochemistry, 25(17), 4929-35, 1986

Stidham, M A, Siedow, J N, McIntosh, T J, Porter, N A, Moreland, D E. Effects of phenylamide herbicides on the physical properties of phosphatidylcholine membranes. Biochim Biophys Acta, 812(3), 721-30, 1985

McIntosh, T J, Simon, S A, Ellington, J C, Porter, N A. New structural model for mixed-chain phosphatidylcholine bilayers. Biochemistry, 23(18), 4038-44, 1984

Porter, N A. Chemistry of lipid peroxidation. Methods Enzymol, 105, 273-82, 1984

Nicholas, A W, Khouri, L G, Ellington, J C, Porter, N A. Synthesis of mixed-acid phosphatidylcholines and high pressure liquid chromatographic analysis of isomeric lysophosphatidylcholines. Lipids, 18(6), 434-8, 1983

Fridovich, S E, Porter, N A. Oxidation of arachidonic acid in micelles by superoxide and hydrogen peroxide. J Biol Chem, 256(1), 260-5, 1981

Porter, N A, Weenen, H. High-performance liquid chromatographic separations of phospholipids and phospholipid oxidation products. Methods Enzymol, 72, 34-40, 1981

Porter, N A, Wolf, R A, Pagels, W R, Marnett, L J. A test for the intermediacy of 11-hydroperoxyeicosa-5,8,12,14-tetraenoic acid [11-HPETE] in prostaglandin biosynthesis. Biochem Biophys Res Commun, 92(2), 349-55, 1980

Siegel, M I, McConnell, R T, Porter, N A, Cuatrecasas, P. Arachidonate metabolism via lipoxygenase and 12L-hydroperoxy-5,8,10,14-icosatetraenoic acid peroxidase sensitive to anti-inflammatory drugs. Proc Natl Acad Sci U S A, 77(1), 308-12, 1980 PMCID:348259

Siegel, M I, McConnell, R T, Porter, N A, Selph, J L, Truax, J F, Vinegar, R, Cuatrecasas, P. Aspirin-like drugs inhibit arachidonic acid metabolism via lipoxygenase and cyclo-oxygenase in rat neutrophils from carrageenan pleural exudates. Biochem Biophys Res Commun, 92(2), 688-95, 1980

Porter, N A, Wolf, R A, Yarbro, E M, Weenen, H. The autoxidation of arachidonic acid: formation of the proposed SRS-A intermediate. Biochem Biophys Res Commun, 89(4), 1058-64, 1979

Siegel, M I, McConnell, R T, Abrahams, S L, Porter, N A, Cuatrecasas, P. Regulation of arachidonate metabolism via lipoxygenase and cyclo-oxygenase by 12-HPETE, the product of human platelet lipoxygenase. Biochem Biophys Res Commun, 89(4), 1273-80, 1979

Porter, N A, Gilmore, D W. 2,3-dioxabicyclo[2.2.1]heptane. J Am Chem Soc, 99(10), 3503-4, 1977

Funk, M O, Isacc, R, Porter, N A. Preparation and purification of lipid hydroperoxides from arachidonic and gamma-linolenic acids. Lipids, 11(2), 113-7, 1976

Menzel, D B, Roycroft, J H, Nixon, J R, Isaac, S R, Porter, N A. Monocyclic peroxides as inhibitors of arachidonic acid and prostaglandin endoperoxide analog initiated aggregation of human platelets. Res Commun Chem Pathol Pharmacol, 15(4), 767-85, 1976

Porter, N A, Funk, M O, Gilmore, D, Isaac, R, Nixon, J. The formation of cyclic peroxides from unsaturated hydroperoxides: Models for prostaglandin biosynthesis. J Am Chem Soc, 98(19), 6000-5, 1976

Porter, N A, Nixon, J, Isaac, R. Cyclic peroxides and the thiobarbituric assay. Biochim Biophys Acta, 441(3), 506-12, 1976

Funk, M O, Isaac, R, Porter, N A. Letter: Free radical cyclization of unsaturated hydroperoxides. J Am Chem Soc, 97(5), 1281-2, 1975

Porter, N A, Funk, M O. Letter: Peroxy radical cyclization as a model for prostaglandin biosynthesis. J Org Chem, 40(24), 3614-5, 1975


Postdoctoral Position Available
Yes

Postdoctoral Position Details
Organic Chemistry, Lipid Oxidation, Free Radical Chemistry

Updated Date
8/26/2003