Publications

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**Publications after 2012 are linked to the journal articles.

2022

Manley, O.M.; Phan, H.N.; Stewart, A.; Mosley, D.A.; Xue, S.; Cha, L.; Bai, H.: Lightfoot, V.; Rucker, P.A.; Collins, L.; Williams, T.I., Chang, W-c; Guo, Y: Makris, T. M., Self-sacrificial tyrosine cleavage by an Fe:Mn oxygenase for the biosynthesis of para-aminobenzoate in Chlamydia trachomatis. Proc. Natl. Acad. Sci. USA

Dutra, M.; McElhenney, S.; Manley, O.M; Makris, T.M.; Rassolov, V.; Garashchuk, S. Modeling the Ligand Effect on the Structure of CYP450 within the Density Functional Theory., J Phys Chem A 2022, 126 (18), 2818- 2824.

Dutra, M.; Amaya, J. A.; McElhenney, S.; Manley, O. M.; Makris, T. M., Rassolov, V.; Garashchuk, S. Experimental and Theoretical Examination of the Kinnetic Isotope Effect in Cytochrome P450 Decarboxylase OleT, J Phys Chem B 2022 126, 3493-3504.

Daneshian, L.; Renggli, I.; Hanaway, R.; Offermann, L. R.; Schlachter, C. R.; Hernandez Arriaza, R.; Henry, S.; Prakash, R.; Wybouw, N.; Dermauw, W.; Shimizu, L. S.; Van Leeuwen, T.; Makris, T. M.; Grbic, V.; Grbic, M.; Chruszcz, M., Structural and functional characterization of beta-cyanoalanine synthase from Tetranychus urticae. Insect Biochem Mol Biol 2022, 142, 103722.

Martin, C. R.; Park, K. C.; Leith, G. A.; Yu, J.; Mathur, A.; Wilson, G. R.; Gange, G. B.; Barth, E. L.; Ly, R. T.; Manley, O. M.; Forrester, K. L.; Karakalos, S. G.; Smith, M. D.; Makris, T. M.; Vannucci, A. K.; Peryshkov, D. V.; Shustova, N. B., Stimuli-Modulated Metal Oxidation States in Photochromic MOFs. J Am Chem Soc 2022, 144 (10), 4457-4468.

2021

Manley, O. M.; Tang, H. Y.; Xue, S.; Guo, Y. S.; Chang, W. C.; Makris, T. M., BesC Initiates C-C Cleavage through a Substrate-Triggered and Reactive Diferric-Peroxo Intermediate. J Am Chem Soc 2021, 143 (50), 21416- 21424.

Manley, O. M.; Makris, T. M., Cytochrome P450 Enzyme Mechanisms. In Reference Module in Chemistry, Molecular Sciences and Chemical Engineering, Elsevier: 2021.

2020

Zhang, L.; Manley, O. M.; Ma, D.; Yin, Y.; Makris, T. M.; Wang, Q., Enhanced P450 fatty acid decarboxylase catalysis by glucose oxidase coupling and co-assembly for biofuel generation. Bioresour Technol 2020, 311, 123538.

Zhang, L.; Beatty, A.; Lu, L.; Abdalrahman, A.; Makris, T. M.; Wang, G.; Wang, Q., Microfluidic-assisted polymer-protein assembly to fabricate homogeneous functional nanoparticles. Mater Sci Eng C Mater Biol Appl 2020, 111, 110768.

Metavarayuth, K.; Ejegbavwo, O.; McCarver, G.; Myrick, M. L.; Makris, T. M.; Vogiatzis, K. D.; Senanayake, S. D.; Manley, O. M.; Ebrahim, A. M.; Frenkel, A. I.; Hwang, S.; Rajeshkumar, T.; Jimenez, J. D.; Chen, K.; Shustova, N. B.; Chen, D. A., Direct Identification of Mixed-Metal Centers in Metal-Organic Frameworks: Cu3(BTC)2 Transmetalated with Rh(2+) Ions. J Phys Chem Lett 2020, 11 (19), 8138-8144.

2019

Manley, O. M.; Fan, R.; Guo, Y.; Makris, T. M., Oxidative Decarboxylase UndA Utilizes a Dinuclear Iron Cofactor. J Am Chem Soc 2019, 141 (22), 8684-8688.

Makris, T. M., Cytochrome P450 Decarboxylases. Rsc Metallobio Ser 2019, 13, 127-143.

Schlachter, C.R., Daneshian, L., Amaya, J., Klapper, V., Wybouw, N., Borowski, T., Van Leeuwen, T., Grbic, V., Grbic, M., Makris, T.M., Chruszcz, M. (2019) Structural and functional characterization of an intradiol ring-cleavage dioxygenase from the polyphagous spider mite herbivore Tetranychus urticae Koch, Insect Biochem. Mol. Biol. 107, 19-30.

Blahut, M.; Wise, C. E.; Bruno, M. R.; Dong, G.; Makris, T. M.; Frantom, P. A.; Dunkle, J. A.; Outten, F. W., Direct observation of intermediates in the SufS cysteine desulfurase reaction reveals functional roles of conserved active-site residues. J. Biol. Chem. 2019, 294 (33), 12444-12458.

Kader, S.; Monavarian, M.; Barati, D.; Moeinzadeh, S.; Makris, T. M.; Jabbari, E., Plasmin-Cleavable Nanoparticles for On-Demand Release of Morphogens in Vascularized Osteogenesis. Biomacromolecules 2019, 20 (8), 2973-2988.

2018

Wise, C. E., Hsieh, C. H., Poplin, N. L. and Makris, T. M. (2018) Dioxygen Activation by the Biofuel-Generating Cytochrome P450 OleT, ACS Catalysis 8 (10) 9342-9352.

Munro, A. W., McLean, K. J., Grant, J. L., Makris, T. M. (2018) Structure and Function of the Cytochrome P450 Peroxygenase Enzymes, Biochemistry Society Transactions

Zhang, L., Xu, Y., Makris, T. M. and Wang, Q. (2018) Enhanced Arylamine N-Oxygenase Activity of Polymer–Enzyme Assemblies by Facilitating Electron-Transferring Efficiency, Biomacromolecules 19 (3) 918-925.

Amaya, J. A., Rutland, C. D., Leschinsky, N., Makris, T. M. (2018) A Distal Loop Controls Product Release and Chemo and Regioselectivity in Cytochrome P450 Decarboxylases, Biochemistry 57 (3) 344-353.

Milazcewska, A. M., Kot, E., Amaya, J. A., Makris, T. M., Zajac, M., Korecki, J., Chumakov, A., Trzewik, B., Minor, W., Chruszcz, M., Borowski, T. M. (2018) On structure and reaction mechanism of human acireductone dioxygenase, Chemistry Eur. J. 24, 1 - 14.

2017

Rahman, Md. M., Smith, M. D., Amaya, J. A., Makris, T. M., and Peryshkov, D. L. (2017) Activation of C-H bonds of Alkyl- and Arylnitriles by the TaCl5-PPh3 Lewis Pair, Inorganic Chemistry 56 (19), 11798-11803.

Khivantsev, K., Biancardi, A., Fathizadeh, M., Almalki, F., Grant, J. L., Tien, H. N., Shakouri, A. N., Blom, D. A., Makris, T. M., Regalbuto, J. R., Caricato, M., and Yu, M. (in press) Catalytic N-H Bond Activation amd Breaking by a Well-defined Co(II)1O4 Site of a Heterogeneous Catalyst, ChemCatChem, Epub ahead of print

Hsieh, C. H., Huang, X., Amaya, J. A., Rutland, C. D., Keys, C. L., Groves, J. T., Austin, R. N., and Makris, T. M. (2017) The Enigmatic P450 Decarboxylase OleT is Capable of, but Evolved to Frustrate, Oxygen Rebound Chemistry, Biochemistry 56 (26), pp 3347–3357

DeHaven, B. A., Tokarski, J. T., Korous, A. A., Mentink-Vigier, F., Makris, T. M., Brugh, A. M., Forbes, M. D. E., van Tol, J., Bowers, C. R., and Shimizu, L. S. (2017) Persistent Radicals of Self-assembled Benzophenone bis-urea Macrocycles: Characterization and Application as a Polarizing Agent for Solid-state DNP MAS Spectroscopy. Chemistry-Eur. J. 23, 8315-8319.

Wise, C. E. and Makris, T.M. (2017) Recruitment and Regulation of the Non-ribosomal Peptide Synthetase Modifying Cytochrome P450 Involved in Nikkomycin Biosynthesis. ACS Chem. Biol. 12 (5) 1316-1326.

Wise, C. E., Grant, J. L., Amaya, J. A., Ratigan, S. C., Hsieh, C.H., Manley, O. M. (2017) Divergent mechanisms of iron-containing enzymes for hydrocarbon biosynthesis. J. Biol. Inorg. Chem. 22 (3) 221-235.

2016

Grant, J. L., Mitchell, M. E., and Makris, T. M. (2016) Catalytic strategy for carbon-carbon bond scission by the cytochrome P450 OleT. Proc. Natl. Acad. Sci. 113 (36), 10049-10054.

Hsieh, C. H., and Makris, T. M. (2016) Expanding the substrate scope and reactivity of cytochrome P450 OleT, Biochem. Biophys. Res. Commun. 476, 462-466.

Amaya, J. A., Rutland, C. D., and Makris, T. M. (2016) Mixed regiospecificity compromises alkene synthesis by a cytochrome P450 peroxygenase from Methylobacterium populi, J. Inorg. Biochem. 158, 11-16.

2015

Grant, J. L., Hsieh, C. H., and Makris, T. M. (2015) Decarboxylation of Fatty Acids to Terminal Alkenes by Cytochrome P450 Compound I. Journal of the American Chemical Society 137, 4940-4943

Makris, T. M., Vu, V. V., Meier, K. K., Komor, A. J., Rivard, B. S., Munck, E., Que, L., and Lipscomb, J. D. (2015) An Unusual Peroxo Intermediate of the Arylamine Oxygenase of the Chloramphenicol Biosynthetic Pathway. Journal of the American Chemical Society 137, 1608-1617

Abeysinghe, D., Gerke, B., Morrison, G., Hsieh, C. H., Smith, M. D., Pottgen, R., Makris, T. M., and zur Loye, H. C. (2015) Synthesis, characterization, and properties of reduced europium molybdates and tungstates. J Solid State Chem 229, 173-180

Knoot, C. J, Makris, T. M., and Lipscomb, J. D. (2015) Dinuclear iron cluster-containing CmlA.  Encyclopedia of Inorganic and Bioinorganic Chemistry, 1-10

2014

Su, S., Panmanee, W., Wilson, J. J., Mahtani, H. K., Li, Q., Vanderwielen, B. D., Makris, T. M., Rogers, M., McDaniel, C., Lipscomb, J. D., Irvin, R. T., Schurr, M. J., Lancaster, J. R., Jr., Kovall, R. A., and Hassett, D. J. (2014) Catalase (KatA) plays a role in protection against anaerobic nitric oxide in Pseudomonas aeruginosa. PloS one 9, e91813

2013

Makris, T. M., Knoot, C. J., Wilmot, C. M., and Lipscomb, J. D. (2013) Structure of a dinuclear iron cluster-containing beta-hydroxylase active in antibiotic biosynthesis. Biochemistry 52, 6662-667

Aukema, K. G., Makris, T. M., Stoian, S. A., Richman, J. E., Munck, E., Lipscomb, J. D., and Wackett, L. P. (2013) Cyanobacterial aldehyde deformylase oxygenation of aldehydes yields n-1 aldehydes and alcohols in addition to alkanes. ACS catalysis 3, 2228-2238

prior to 2013

Thompson, J. W., Salahudeen, A. A., Chollangi, S., Ruiz, J. C., Brautigam, C. A., Makris, T. M., Lipscomb, J. D., Tomchick, D. R., and Bruick, R. K. (2012) Structural and molecular characterization of iron-sensing hemerythrin-like domain within F-box and leucine-rich repeat protein 5 (FBXL5), J. Biol. Chem. 287, 7357-7365.

Vu, V. V., Makris, T. M., Lipscomb, J. D., and Que, L., Jr. (2011) Active-site structure of a beta-hydroxylase in antibiotic biosynthesis, J. Am. Chem. Soc. 133, 6938-6941.

Makris, T. M., Chakrabarti, M., Munck, E., and Lipscomb, J. D. (2010) A family of diiron monooxygenases catalyzing amino acid beta-hydroxylation in antibiotic biosynthesis, Proceedings of the National Academy of Sciences of the United States of America 107, 15391-15396.

Denisov, I. G., Mak, P. J., Makris, T. M., Sligar, S. G., and Kincaid, J. R. (2008) Resonance Raman characterization of the peroxo and hydroperoxo intermediates in cytochrome P450, J. Phys. Chem. A 112, 13172-13179.

Makris, T. M., von Koenig, K., Schlichting, I., and Sligar, S. G. (2007) Alteration of P450 distal pocket solvent leads to impaired proton delivery and changes in heme geometry, Biochemistry 46, 14129-14140.

Mak, P. J., Denisov, I. G., Victoria, D., Makris, T. M., Deng, T., Sligar, S. G., and Kincaid, J. R. (2007) Resonance Raman detection of the hydroperoxo intermediate in the cytochrome P450 enzymatic cycle, J. Am. Chem. Soc. 129, 6382-6383.

Newcomb, M., Zhang, R., Chandrasena, R. E., Halgrimson, J. A., Horner, J. H., Makris, T. M., and Sligar, S. G. (2006) Cytochrome p450 compound I, J. Am. Chem. Soc. 128, 4580-4581.

Makris, T. M., von Koenig, K., Schlichting, I., and Sligar, S. G. (2006) The status of high-valent metal oxo complexes in the P450 cytochromes, J. Inorg. Biochem. 100, 507-518.

Sligar, S. G., Makris, T. M., and Denisov, I. G. (2005) Thirty years of microbial P450 monooxygenase research: peroxo-heme intermediates--the central bus station in heme oxygenase catalysis, Biochem. Biophys. Res. Commun. 338, 346-354.

Denisov, I. G., Makris, T. M., Sligar, S. G., and Schlichting, I. (2005) Structure and chemistry of cytochrome P450, Chem. Rev. 105, 2253-2277.

Ke, N., Baudry, J., Makris, T. M., Schuler, M. A., and Sligar, S. G. (2005) A retinoic acid binding cytochrome P450: CYP120A1 from Synechocystis sp. PCC 6803, Arch. Biochem. Biophys. 436, 110-120.

Sono, M., Perera, R., Jin, S., Makris, T. M., Sligar, S. G., Bryson, T. A., and Dawson, J. H. (2005) The influence of substrate on the spectral properties of oxyferrous wild-type and T252A cytochrome P450-CAM, Arch. Biochem. Biophys. 436, 40-49.

Ibrahim, M., Denisov, I. G., Makris, T. M., Kincaid, J. R., and Sligar, S. G. (2003) Resonance Raman spectroscopic studies of hydroperoxo-myoglobin at cryogenic temperatures, J. Am. Chem. Soc. 125, 13714-13718.

Jin, S., Makris, T. M., Bryson, T. A., Sligar, S. G., and Dawson, J. H. (2003) Epoxidation of olefins by hydroperoxo-ferric cytochrome P450, J. Am. Chem. Soc. 125, 3406-3407.

Makris, T. M., Davydov, R., Denisov, I. G., Hoffman, B. M., and Sligar, S. G. (2002) Mechanistic enzymology of oxygen activation by the cytochromes P450, Drug Metab. Rev. 34, 691-708.

Denisov, I. G., Makris, T. M., and Sligar, S. G. (2002) Formation and decay of hydroperoxo-ferric heme complex in horseradish peroxidase studied by cryoradiolysis, J. Biol. Chem. 277, 42706-42710.

Davydov, R., Makris, T. M., Kofman, V., Werst, D. E., Sligar, S. G., and Hoffman, B. M. (2001) Hydroxylation of camphor by reduced oxy-cytochrome P450cam: mechanistic implications of EPR and ENDOR studies of catalytic intermediates in native and mutant enzymes, J. Am. Chem. Soc. 123, 1403-1415.

Denisov, I. G., Makris, T. M., and Sligar, S. G. (2001) Cryotrapped reaction intermediates of cytochrome p450 studied by radiolytic reduction with phosphorus-32, J. Biol. Chem. 276, 11648-11652.

Davydov, R., Macdonald, I. D. G., Makris, T. M., Sligar, S. G., and Hoffman, B. M. (1999) EPR and ENDOR of catalytic intermediates in cryoreduced native and mutant oxy-cytochromes P450cam: Mutation-induced changes in the proton delivery system, J. Am. Chem. Soc. 121, 10654-10655.