Works (63)

Updated: April 4th, 2024 03:07

2024 journal article

Enhancing ferryl accumulation in H2O2-dependent cytochrome P450s

JOURNAL OF INORGANIC BIOCHEMISTRY, 252.

By: J. Amaya*, O. Manley n, J. Bian*, C. Rutland*, N. Leschinsky*, S. Ratigan*, T. Makris n

author keywords: Cytochrome P450; Compound I; Ferryl; CYP152; Peroxygenase
Sources: Web Of Science, NC State University Libraries
Added: February 12, 2024

2023 journal article

A Ferric-Superoxide Intermediate Initiates P450-Catalyzed Cyclic Dipeptide Dimerization

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 8.

By: H. Gering n, X. Li n, H. Tang n, P. Swartz n, W. Chang n & T. Makris n

Sources: Web Of Science, ORCID, NC State University Libraries
Added: September 11, 2023

2023 journal article

Dimer-assisted mechanism of (un)saturated fatty acid decarboxylation for alkene production

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 120(22).

By: L. Rade*, W. Generoso*, S. Das n, A. Souza*, R. Silveira*, M. Avila*, P. Vieira*, R. Miyamoto* ...

author keywords: CYP152 peroxygenase; decarboxylation activity; molecular mechanism; alkene production; renewable hydrocarbons
MeSH headings : Fatty Acids / metabolism; Alkenes / chemistry; Decarboxylation; Cytochrome P-450 Enzyme System / metabolism; Oxidation-Reduction
TL;DR: It is shown that the dimeric configuration of OleTPRN is involved in the stabilization of the A-A' helical motif, a second-coordination sphere of the substrate, which contributes to the proper accommodation of the aliphatic tail in the distal and medial active-site pocket, creating new opportunities for biological production of renewable hydrocarbons. (via Semantic Scholar)
Sources: Web Of Science, NC State University Libraries
Added: August 7, 2023

2023 journal article

Excision of a Protein-Derived Amine for <i>p</i>-Aminobenzoate Assembly by the Self-Sacrificial Heterobimetallic Protein CADD

BIOCHEMISTRY, 62(22), 3276–3282.

By: H. Phan n, O. Manley n, S. Skirboll n, L. Cha n, D. Hilovsky n, W. Chang n, P. Thompson n, X. Liu n, T. Makris n

TL;DR: Turnover studies using limiting O2 have identified a para-aminobenzaldehyde metabolic intermediate that is formed on the path to pABA formation and use of pABCHO and other probe substrates shows that the heterobimetallic Fe/Mn form of the enzyme is capable of oxygen insertion to generate the pA BA-carboxylate. (via Semantic Scholar)
Sources: ORCID, Web Of Science, NC State University Libraries
Added: December 12, 2023

2023 article

Room-Temperature Aerobic C-CN Bond Activation in Nickel(II) Cyanomethyl Dicarboranyl Complex

Islam, M. J., Park, K. C., Manley, O. M. M., Smith, M. D. D., Makris, T. M. M., & Peryshkov, D. V. V. (2023, July 12). ORGANOMETALLICS, Vol. 7.

UN Sustainable Development Goal Categories
Sources: Web Of Science, ORCID, NC State University Libraries
Added: July 24, 2023

2022 journal article

Experimental and Theoretical Examination of the Kinetic Isotope Effect in Cytochrome P450 Decarboxylase OleT

JOURNAL OF PHYSICAL CHEMISTRY B, 126(19), 3493–3504.

MeSH headings : Carboxy-Lyases / metabolism; Cytochrome P-450 Enzyme System / chemistry; Fatty Acids / chemistry; Hydrogen / chemistry; Isotopes; Kinetics
TL;DR: A more fundamental understanding of the OleT reaction coordinate contributes to the development of biomimetic catalysts for controlled C─H bond activation, an outstanding current challenge for (bio)synthetic chemistry. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Sources: Web Of Science, ORCID, NC State University Libraries
Added: June 13, 2022

2022 journal article

Modeling the Ligand Effect on the Structure of CYP 450 Within the Density Functional Theory

JOURNAL OF PHYSICAL CHEMISTRY A, 126(18), 2818–2824.

MeSH headings : Cysteine / chemistry; Density Functional Theory; Heme / chemistry; Iron / chemistry; Ligands
UN Sustainable Development Goal Categories
Sources: Web Of Science, ORCID, NC State University Libraries
Added: June 6, 2022

2022 journal article

Self-sacrificial tyrosine cleavage by an Fe:Mn oxygenase for the biosynthesis of para-aminobenzoate in Chlamydia trachomatis

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 119(39).

By: O. Manley n, H. Phan n, A. Stewart n, D. Mosley n, S. Xue*, L. Cha n, H. Bai n, V. Lightfoot* ...

Contributors: T. Williams n

author keywords: folate biosynthesis; radical transfer; spectroscopy; heterobinuclear cluster
MeSH headings : Bacterial Proteins / metabolism; Chlamydia trachomatis / enzymology; Folic Acid; Iron / metabolism; Manganese / metabolism; Oxygen / metabolism; Oxygenases / metabolism; Tyrosine / metabolism; para-Aminobenzoates / metabolism
TL;DR: High in vitro activity relies on the stoichiometric addition of both Fe and Mn, and CADD is shown to activate O2 to self-sacrificially produce pABA from Tyr27. (via Semantic Scholar)
Sources: Web Of Science, NC State University Libraries, ORCID
Added: September 21, 2022

2022 journal article

Stimuli-Modulated Metal Oxidation States in Photochromic MOFs

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 144(10), 4457–4468.

By: C. Martin*, K. Park*, G. Leith*, J. Yu*, A. Mathur*, G. Wilson*, G. Gange*, E. Barth* ...

MeSH headings : Metal-Organic Frameworks / chemistry; Metals; Oxidation-Reduction
UN Sustainable Development Goal Categories
Sources: Web Of Science, NC State University Libraries
Added: April 18, 2022

2022 journal article

Structural and functional characterization of beta-cyanoalanine synthase from Tetranychus urticae

INSECT BIOCHEMISTRY AND MOLECULAR BIOLOGY, 142.

By: L. Daneshian*, I. Renggli*, R. Hanaway*, L. Offermann*, C. Schlachter*, S. Henry*, R. Prakash*, N. Wybouw* ...

author keywords: beta-cyanoalanine synthase; Cyanide detoxification; Cyanoalanine; Herbivory; Spider mite
MeSH headings : Animals; Cyanides / metabolism; Cysteine; Lyases / chemistry; Lyases / genetics; Lyases / metabolism; Plants / metabolism; Tetranychidae / metabolism
Sources: Web Of Science, NC State University Libraries
Added: May 2, 2022

2021 article

BesC Initiates C-C Cleavage through a Substrate-Triggered and Reactive Diferric-Peroxo Intermediate

Manley, O. M., Tang, H., Xue, S., Guo, Y., Chang, W.-chen, & Makris, T. M. (2021, December 13). JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, Vol. 12.

By: O. Manley n, H. Tang n, S. Xue*, Y. Guo*, W. Chang n & T. Makris n

MeSH headings : Carbon / chemistry; Carbon / metabolism; Ferric Compounds / chemistry; Oxidoreductases / metabolism; Oxygen / chemistry; Spectroscopy, Mossbauer; Streptomyces / enzymology; Substrate Specificity
TL;DR: The observed reactivity of BesC represents the first example of a dinuclear-iron enzyme that utilizes a diferric-peroxo intermediate to capably cleave a C-H bond as part of its native function, thus circumventing the formation of a high-valent intermediate more commonly associated with substrate monooxygenations. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Sources: Web Of Science, ORCID, NC State University Libraries
Added: January 3, 2022

2020 journal article

Direct Identification of Mixed-Metal Centers in Metal-Organic Frameworks: Cu<inf>3</inf>(BTC)<inf>2</inf>Transmetalated with Rh<sup>2+</sup>Ions

Journal of Physical Chemistry Letters, 11(19), 8138–8144.

TL;DR: Electron paramagnetic resonance (EPR) spectroscopy experiments further support the conclusion that Rh2+ ions are substituted into the paddle-wheel nodes of the Cu3(BTC)2 to form an isostructural heterometallic MOF, and electron microscopy studies show that Rh and Cu are homogenously distributed in CuRhBTC on the nanoscale. (via Semantic Scholar)
Source: ORCID
Added: December 12, 2023

2020 journal article

Enhanced P450 fatty acid decarboxylase catalysis by glucose oxidase coupling and co-assembly for biofuel generation

Bioresource Technology, 311.

Contributors: L. Zhang*, O. Manley*, D. Ma*, Y. Yin*, T. Makris* & Q. Wang*

TL;DR: An artificial enzyme cascade composed of glucose oxidase (GOx) and OleTSA from Staphylococcus aureus for efficient terminal alkene production is reported, showing significantly improved product yield and improved activity compared to the H2O2 injection method. (via Semantic Scholar)
Source: ORCID
Added: December 12, 2023

2020 journal article

Microfluidic-assisted polymer-protein assembly to fabricate homogeneous functionalnanoparticles

Materials Science and Engineering C, 111.

By: L. Zhang*, A. Beatty*, L. Lu*, A. Abdalrahman*, T. Makris*, G. Wang*, Q. Wang*

Contributors: L. Zhang*, A. Beatty*, L. Lu*, A. Abdalrahman*, T. Makris*, G. Wang*, Q. Wang*

TL;DR: The resultant NPs show significantly improved size distribution by comparison with the ones prepared using conventional bulk method, while the NPs size can be tuned by adjusting the mass ratio of polymer to protein. (via Semantic Scholar)
Source: ORCID
Added: December 12, 2023

2019 chapter

CHAPTER 6: Cytochrome P450 Decarboxylases

In RSC Metallobiology: Vol. 2019-January (pp. 127–143).

By: T. Makris*

Contributors: T. Makris*

TL;DR: The intriguing molecular mechanism of OleT and its potential for fungible fuel production is reviewed, revealing an interesting deviation from the activated oxygen-rebound chemistry that is common to most P450 monooxygenases. (via Semantic Scholar)
Source: ORCID
Added: December 12, 2023

2019 journal article

Direct observation of intermediates in the SufS cysteine desulfurase reaction reveals functional roles of conserved active-site residues

Journal of Biological Chemistry, 294(33), 12444–12458.

By: M. Blahut*, C. Wise*, M. Bruno*, G. Dong*, T. Makris*, P. Frantom*, J. Dunkle*, F. Outten*

Contributors: M. Blahut*, C. Wise*, M. Bruno*, G. Dong*, T. Makris*, P. Frantom*, J. Dunkle*, F. Outten*

TL;DR: A detailed model of the SufS-catalyzed reaction from Cys binding to C–S bond cleavage is suggested and it is suggested that Arg-56, His-123, and Cys-364 are criticalSufS residues in this C-S bond Cleavage pathway. (via Semantic Scholar)
UN Sustainable Development Goal Categories
6. Clean Water and Sanitation (OpenAlex)
Source: ORCID
Added: December 12, 2023

2019 journal article

Oxidative Decarboxylase UndA Utilizes a Dinuclear Iron Cofactor

Journal of the American Chemical Society, 141(22), 8684–8688.

By: O. Manley*, R. Fan*, Y. Guo* & T. Makris*

Contributors: O. Manley*, R. Fan*, Y. Guo* & T. Makris*

TL;DR: The first optical and Mössbauer spectroscopic characterization of UndA is reported, revealing that the enzyme harbors a coupled dinuclear iron cluster and is the first characterized example of a diiron decarboxylase. (via Semantic Scholar)
UN Sustainable Development Goal Categories
6. Clean Water and Sanitation (OpenAlex)
Source: ORCID
Added: December 12, 2023

2019 journal article

Plasmin-Cleavable Nanoparticles for On-Demand Release of Morphogens in Vascularized Osteogenesis

Biomacromolecules, 20(8), 2973–2988.

By: S. Kader*, M. Monavarian*, D. Barati*, S. Moeinzadeh*, T. Makris* & E. Jabbari*

Contributors: S. Kader*, M. Monavarian*, D. Barati*, S. Moeinzadeh*, T. Makris* & E. Jabbari*

TL;DR: P2SPCP NPs showed high particle size stability, BMP2 grafting efficiency, grafted protein stability, and high extent of osteogenic differentiation of hMSCs, and not only enhances osteogenesis and vasculogenesis but also potentially reduces many undesired side effects of B MP2 therapy in bone regeneration. (via Semantic Scholar)
Source: ORCID
Added: December 12, 2023

2019 journal article

Structural and functional characterization of an intradiol ring-cleavage dioxygenase from the polyphagous spider mite herbivore Tetranychus urticae Koch

Insect Biochemistry and Molecular Biology, 107, 19–30.

By: C. Schlachter*, L. Daneshian*, J. Amaya*, V. Klapper*, N. Wybouw*, T. Borowski*, T. Leeuwen*, V. Grbic* ...

Contributors: C. Schlachter*, L. Daneshian*, J. Amaya*, V. Klapper*, N. Wybouw*, T. Borowski*, T. Van Leeuwen*, V. Grbic* ...

TL;DR: Tetur07g02040 is not only the first spider mite dioxygenase that has been characterized at the molecular level, but is also the first structurally characterized intradiol ring-cleavage dioXYgenase originating from a eukaryote. (via Semantic Scholar)
Source: ORCID
Added: December 12, 2023

2019 journal article

The Diiron Monooxygenase CmlA from Chloramphenicol Biosynthesis Allows Reconstitution of β-Hydroxylation during Glycopeptide Antibiotic Biosynthesis

ACS Chemical Biology, 14(12), 2932–2941.

By: M. Kaniusaite*, R. Goode*, R. Schittenhelm*, T. Makris* & M. Cryle*

Contributors: M. Kaniusaite*, R. Goode*, R. Schittenhelm*, T. Makris* & M. Cryle*

TL;DR: The results from this study show that CmlA has a broad substrate specificity for modified phenylalanine/tyrosine residues as substrates and can be used in a practical strategy to functionally cross complement compatible NRPS biosynthesis pathways in vitro. (via Semantic Scholar)
Source: ORCID
Added: December 12, 2023

2018 journal article

A Distal Loop Controls Product Release and Chemo- and Regioselectivity in Cytochrome P450 Decarboxylases

Biochemistry, 57(3), 344–353.

By: J. Amaya*, C. Rutland*, N. Leschinsky* & T. Makris*

Contributors: J. Amaya*, C. Rutland*, N. Leschinsky* & T. Makris*

TL;DR: This work probes the influence of substrate coordination on OleT reaction partitioning through the combined use of fluorescent and electron paramagnetic resonance-active FA probes and mutagenesis of a structurally disordered F-G loop that is distal from the heme-iron active site. (via Semantic Scholar)
Source: ORCID
Added: December 12, 2023

2018 journal article

Catalytic N−H Bond Activation and Breaking by a Well-Defined Co<sup>II</sup><inf>1</inf>O<inf>4</inf> Site of a Heterogeneous Catalyst

ChemCatChem, 10(4), 736–742.

By: K. Khivantsev*, A. Biancardi*, M. Fathizadeh*, F. Almalki*, J. Grant*, H. Tien*, A. Shakouri*, D. Blom* ...

Contributors: K. Khivantsev*, A. Biancardi*, M. Fathizadeh*, F. Almalki*, J. Grant*, H. Tien*, A. Shakouri*, D. Blom* ...

Source: ORCID
Added: December 12, 2023

2018 journal article

Dioxygen Activation by the Biofuel-Generating Cytochrome P450 OleT

ACS Catalysis, 8(10), 9342–9352.

By: C. Wise*, C. Hsieh*, N. Poplin* & T. Makris*

Contributors: C. Wise*, C. Hsieh*, N. Poplin* & T. Makris*

TL;DR: Transient kinetics, cryoradiolysis, and steady state turnover are applied to implicating a mechanism whereby OleT can generate Compound I via a canonical P450 O2 dependent reaction scheme. (via Semantic Scholar)
Source: ORCID
Added: December 12, 2023

2018 journal article

Enhanced Arylamine N -Oxygenase Activity of Polymer-Enzyme Assemblies by Facilitating Electron-Transferring Efficiency

Biomacromolecules, 19(3), 918–925.

By: L. Zhang*, Y. Xu*, T. Makris* & Q. Wang*

Contributors: L. Zhang*, Y. Xu*, T. Makris* & Q. Wang*

TL;DR: A novel N-oxygenase-coated core-shell nanoparticle was generated through the coassembly of poly(4-vinylpyridine) (P4VP) and arylamine N- oxygengenase CmlI, which exhibited a significantly enhanced catalytic efficiency when using pyridine nucleotide (NADH) and proper redox mediators. (via Semantic Scholar)
Source: ORCID
Added: December 12, 2023

2018 journal article

On the Structure and Reaction Mechanism of Human Acireductone Dioxygenase

Chemistry - A European Journal, 24(20), 5225–5237.

By: A. Mi?aczewska, E. Kot*, J. Amaya*, T. Makris*, M. Zaj?c, J. Korecki*, A. Chumakov*, B. Trzewik* ...

Contributors: A. Miłaczewska*, E. Kot*, J. Amaya*, T. Makris*, M. Zając*, J. Korecki*, A. Chumakov*, B. Trzewik* ...

TL;DR: The crystal structure of an ARD from Homo sapiens was determined with selenomethionine and major features of Fe vibrational spectra obtained for the native enzyme and upon addition of acireductone were reproduced by QM/MM calculations for the proposed models. (via Semantic Scholar)
Source: ORCID
Added: December 12, 2023

2018 journal article

Structure and function of the cytochrome P450 peroxygenase enzymes

Biochemical Society Transactions, 46(1), 183–196.

By: A. Munro*, K. McLean*, J. Grant* & T. Makris*

Contributors: A. Munro*, K. McLean*, J. Grant* & T. Makris*

TL;DR: The biochemical properties of the P450 peroxygenases are focused on and on their biotechnological applications with respect to production of volatile alkenes as biofuels, as well as other fine chemicals. (via Semantic Scholar)
Source: ORCID
Added: December 12, 2023

2017 journal article

Activation of C-H Bonds of Alkyl- and Arylnitriles by the TaCl<inf>5</inf>-PPh<inf>3</inf> Lewis Pair

Inorganic Chemistry, 56(19), 11798–11803.

By: M. Rahman*, M. Smith*, J. Amaya*, T. Makris* & D. Peryshkov*

Contributors: M. Rahman*, M. Smith*, J. Amaya*, T. Makris* & D. Peryshkov*

TL;DR: These transformations highlight the special role of the high-valent transition metal halide in substrate activation and distinguish the reactivity of the TaCl5-PPh3 system from both non-metal- and late transition metal-based frustrated Lewis pairs. (via Semantic Scholar)
UN Sustainable Development Goal Categories
6. Clean Water and Sanitation (OpenAlex)
Source: ORCID
Added: December 12, 2023

2017 journal article

Divergent mechanisms of iron-containing enzymes for hydrocarbon biosynthesis

Journal of Biological Inorganic Chemistry, 22(2-3), 221–235.

By: C. Wise*, J. Grant*, J. Amaya*, S. Ratigan*, C. Hsieh*, O. Manley*, T. Makris*

Contributors: C. Wise*, J. Grant*, J. Amaya*, S. Ratigan*, C. Hsieh*, O. Manley*, T. Makris*

TL;DR: This review examines the mechanisms of several enzymes involved in hydrocarbon biosynthesis, with specific emphasis on the structural and electronic changes that enable this functional switch. (via Semantic Scholar)
Source: ORCID
Added: December 12, 2023

2017 journal article

Persistent Radicals of Self-assembled Benzophenone bis-Urea Macrocycles: Characterization and Application as a Polarizing Agent for Solid-state DNP MAS Spectroscopy

Chemistry - A European Journal, 23(34), 8315–8319.

By: B. DeHaven*, J. Tokarski*, A. Korous*, F. Mentink‐Vigier*, T. Makris*, A. Brugh*, M. Forbes*, J. Tol*, C. Bowers*, L. Shimizu*

Contributors: B. DeHaven*, J. Tokarski*, A. Korous*, F. Mentink-Vigier*, T. Makris*, A. Brugh*, M. Forbes*, J. Tol*, C. Bowers*, L. Shimizu*

TL;DR: UV-irradiation of a self-assembled benzophenone bis-urea macrocycle generates μm amounts of radicals that persist for weeks under ambient conditions, suggesting that even low levels of endogenous radicals can facilitate the study of host-guest relationships in the solid-state. (via Semantic Scholar)
Source: ORCID
Added: December 12, 2023

2017 journal article

Recruitment and Regulation of the Non-ribosomal Peptide Synthetase Modifying Cytochrome P450 Involved in Nikkomycin Biosynthesis

ACS Chemical Biology, 12(5), 1316–1326.

By: C. Wise* & T. Makris*

Contributors: C. Wise* & T. Makris*

TL;DR: Electrochemistry and transient kinetics have been used to probe the influence of l-His-NikP1 binding on catalysis by NikQ, demonstrating a complex interplay between the NRPS maturation process and the recruitment and regulation of an auxiliary tailoring enzyme required for natural product biosynthesis. (via Semantic Scholar)
Source: ORCID
Added: December 12, 2023

2017 journal article

The Enigmatic P450 Decarboxylase OleT Is Capable of, but Evolved to Frustrate, Oxygen Rebound Chemistry

Biochemistry, 56(26), 3347–3357.

By: C. Hsieh*, X. Huang*, J. Amaya*, C. Rutland*, C. Keys*, J. Groves*, R. Austin*, T. Makris*

Contributors: C. Hsieh*, X. Huang*, J. Amaya*, C. Rutland*, C. Keys*, J. Groves*, R. Austin*, T. Makris*

TL;DR: Transient kinetics and product analyses confirm that OleT capably activates hydrogen peroxide with shorter substrates to form the high-valent intermediate Compound I and largely performs C-C bond scission. (via Semantic Scholar)
Source: ORCID
Added: December 12, 2023

2016 journal article

Catalytic strategy for carbon-carbon bond scission by the cytochrome p450 olet

Proceedings of the National Academy of Sciences of the United States of America, 113(36), 10049–10054.

By: J. Grant*, M. Mitchell* & T. Makris*

Contributors: J. Grant*, M. Mitchell* & T. Makris*

TL;DR: Rapid kinetics studies reveal two critical reaction cycle intermediates that define the catalytic strategy used by OleT and highlight the functional versatility of P450 enzymes. (via Semantic Scholar)
Source: ORCID
Added: December 12, 2023

2016 journal article

Expanding the substrate scope and reactivity of cytochrome P450 OleT

Biochemical and Biophysical Research Communications, 476(4), 462–466.

By: C. Hsieh* & T. Makris*

Contributors: C. Hsieh* & T. Makris*

TL;DR: Spectroscopic and turnover studies show that the mutation eliminates the binding and metabolism of prototypical fatty acid substrates, but permits the oxidation of a broad range of inert hydrocarbon substrates. (via Semantic Scholar)
UN Sustainable Development Goal Categories
6. Clean Water and Sanitation (OpenAlex)
Source: ORCID
Added: December 12, 2023

2016 journal article

Mixed regiospecificity compromises alkene synthesis by a cytochrome P450 peroxygenase from Methylobacterium populi

Journal of Inorganic Biochemistry, 158, 11–16.

By: J. Amaya*, C. Rutland* & T. Makris*

Contributors: J. Amaya*, C. Rutland* & T. Makris*

TL;DR: It is shown that a second CYP152, CYP-MP from Methylobacterium populi ATCC BAA 705, also catalyzes oxidative substrate decarboxylation, suggesting an importance of substrate coordination for regulating alkene production. (via Semantic Scholar)
Source: ORCID
Added: December 12, 2023

2015 journal article

An unusual peroxo intermediate of the arylamine oxygenase of the chloramphenicol biosynthetic pathway

Journal of the American Chemical Society, 137(4), 1608–1617.

By: T. Makris*, V. Vu, K. Meier*, A. Komor, B. Rivard, E. Münck*, L. Que, J. Lipscomb

Contributors: T. Makris*, V. Vu, K. Meier*, A. Komor, B. Rivard, E. Münck*, L. Que, J. Lipscomb

TL;DR: Efficient production of chloramphenicol from the free arylamine precursor suggests that CmlI catalyzes the ultimate step in the biosynthetic pathway and that the precursor is not bound to the NRPS during this step. (via Semantic Scholar)
Source: ORCID
Added: December 12, 2023

2015 journal article

Decarboxylation of fatty acids to terminal alkenes by cytochrome P450 compound i

Journal of the American Chemical Society, 137(15), 4940–4943.

By: J. Grant*, C. Hsieh* & T. Makris*

Contributors: J. Grant*, C. Hsieh* & T. Makris*

TL;DR: Results indicate that the initial mechanism for alkene formation, which does not result from oxygen rebound, is similar to that widely suggested for P450 monooxygenation reactions. (via Semantic Scholar)
UN Sustainable Development Goal Categories
6. Clean Water and Sanitation (OpenAlex)
Source: ORCID
Added: December 12, 2023

2015 journal article

Synthesis, characterization, and properties of reduced europium molybdates and tungstates

Journal of Solid State Chemistry, 229, 173–180.

By: D. Abeysinghe*, B. Gerke*, G. Morrison*, C. Hsieh*, M. Smith*, R. Pöttgen*, T. Makris*, H. Loye*

Contributors: D. Abeysinghe*, B. Gerke*, G. Morrison*, C. Hsieh*, M. Smith*, R. Pöttgen*, T. Makris*, H. Zur Loye*

Source: ORCID
Added: December 12, 2023

2014 journal article

Catalase (KatA) Plays a role in protection against anaerobic nitric oxide in Pseudomonas aeruginosa

PLoS ONE, 9(3).

Contributors: S. Su*, W. Panmanee*, J. Wilson*, H. Mahtani*, Q. Li*, B. VanderWielen*, T. Makris*, M. Rogers* ...

TL;DR: KatA is expressed to protect PA against NO generated during anaerobic respiration and it is proposed that such protective effects of KatA may involve buffering of free NO when potentially toxic concentrations of NO are approached. (via Semantic Scholar)
Source: ORCID
Added: December 12, 2023

2013 journal article

Cyanobacterial aldehyde deformylase oxygenation of aldehydes yields n - 1 aldehydes and alcohols in addition to alkanes

ACS Catalysis, 3(10), 2228–2238.

By: K. Aukema*, T. Makris*, S. Stoian*, J. Richman*, E. Münck*, J. Lipscomb*, L. Wackett*

Contributors: K. Aukema*, T. Makris*, S. Stoian*, J. Richman*, E. Münck*, J. Lipscomb*, L. Wackett*

TL;DR: It is shown that ADO also catalyzes incorporation of an oxygen atom from O2 into the alkane product to yield alcohol and aldehyde products, and the nature of the diiron cluster and the newly recognized products from ADO catalysis hold implications for the mechanism of C-C bond cleavage. (via Semantic Scholar)
Source: ORCID
Added: December 12, 2023

2013 journal article

Structure of a dinuclear iron cluster-containing β-hydroxylase active in antibiotic biosynthesis

Biochemistry, 52(38), 6662–6671.

Contributors: T. Makris*, C. Knoot*, C. Wilmot* & J. Lipscomb*

TL;DR: The 2.17 Å X-ray crystal structure of the archetypal enzyme from the NRPS family, CmlA, is reported and it is hypothesize that it likely serves additional roles in NRPS recognition and the regulation of O2 activation. (via Semantic Scholar)
Source: ORCID
Added: December 12, 2023

2012 journal article

Structural and molecular characterization of iron-sensing hemerythrin-like domain within F-box and leucine-rich repeat protein 5 (FBXL5)

Journal of Biological Chemistry, 287(10), 7357–7365.

By: J. Thompson*, A. Salahudeen*, S. Chollangi*, J. Ruiz*, C. Brautigam*, T. Makris*, J. Lipscomb*, D. Tomchick*, R. Bruick*

Contributors: J. Thompson*, A. Salahudeen*, S. Chollangi*, J. Ruiz*, C. Brautigam*, T. Makris*, J. Lipscomb*, D. Tomchick*, R. Bruick*

TL;DR: The atomic structure of the FBXL5 N terminus is presented, a hemerythrin-like α-helical bundle fold not previously observed in mammalian proteins, which provides insights into the mechanisms by whichFBXL5 serves as a unique mammalian metabolic sensor. (via Semantic Scholar)
Source: ORCID
Added: December 12, 2023

2011 journal article

Active-site structure of a β-hydroxylase in antibiotic biosynthesis

Journal of the American Chemical Society, 133(18), 6938–6941.

Contributors: V. Vu*, T. Makris*, J. Lipscomb* & L. Que Jr.

TL;DR: X-ray absorption and resonance Raman spectroscopies show that CmlA, the β-hydroxylase of the chloramphenicol biosynthetic pathway, contains a (μ-oxo)-(μ-1,3-carboxylato)diiron(III) cluster with 6-coordinate iron centers and 3 - 4 His ligands. (via Semantic Scholar)
Source: ORCID
Added: December 12, 2023

2011 article

Dinuclear Iron Cluster-Containing Oxygenase CmlA

Encyclopedia of Inorganic and Bioinorganic Chemistry.

By: C. Knoot*, T. Makris* & J. Lipscomb*

TL;DR: CmlA is the first diiron cluster-containing enzyme known to be active in an NRPS pathway, but a gene search reveals numerous homologs of CmlA that are likely to catalyze similar reactions during biosynthesis of other natural products. (via Semantic Scholar)
Source: ORCID
Added: December 12, 2023

2010 journal article

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(35), 15391–15396.

By: T. Makris*, M. Chakrabarti*, E. Münck* & J. Lipscomb*

Contributors: T. Makris*, M. Chakrabarti*, E. Münck* & J. Lipscomb*

TL;DR: It is shown that CmlA contains an oxo-bridged dinuclear iron cluster, a metal center not previously associated with nonribosomal peptide synthetase chemistry, suggesting that the diiron cluster is in a protein environment not previously known to effect monooxygenase reactions. (via Semantic Scholar)
Source: ORCID
Added: December 12, 2023

2008 journal article

Resonance Raman characterization of the peroxo and hydroperoxo intermediates in cytochrome P450

Journal of Physical Chemistry A, 112(50), 13172–13179.

By: I. Denisov*, P. Mak*, T. Makris*, S. Sligar* & J. Kincaid*

Contributors: I. Denisov*, P. Mak*, T. Makris*, S. Sligar* & J. Kincaid*

TL;DR: Experimental Resonance Raman studies of intermediates generated by cryoreduction of the oxyferrous complex of the D251N mutant of cytochrome P450(cam) (CYP101) are reported, showing that the nu(O-O) mode decreases from a superoxo-like frequency near approximately 1130 cm(-1) to 792 cm (-1) upon reduction. (via Semantic Scholar)
Source: ORCID
Added: December 12, 2023

2007 journal article

Alteration of P450 distal pocket solvent leads to impaired proton delivery and changes in heme geometry

Biochemistry, 46(49), 14129–14140.

By: T. Makris*, K. Von Koenig*, I. Schlichting* & S. Sligar*

Contributors: T. Makris*, K. Von Koenig*, I. Schlichting* & S. Sligar*

TL;DR: Results indicate that the distal pocket microenvironment governs the transformation of reactive heme-oxygen intermediates in P450 cytochromes. (via Semantic Scholar)
UN Sustainable Development Goal Categories
6. Clean Water and Sanitation (OpenAlex)
Source: ORCID
Added: December 12, 2023

2007 journal article

Resonance Raman detection of the hydroperoxo intermediate in the cytochrome P450 enzymatic cycle

Journal of the American Chemical Society, 129(20), 6382–6383.

By: P. Mak*, I. Denisov*, D. Victoria*, T. Makris*, T. Deng*, S. Sligar*, J. Kincaid*

Contributors: P. Mak*, I. Denisov*, D. Victoria*, T. Makris*, T. Deng*, S. Sligar*, J. Kincaid*

TL;DR: The resonance Raman spectra of the hydroperoxo complex of camphor-bound CYP101 have been obtained by cryoradiolytic reduction of the oxygenated ferrous form that had been rapidly frozen in water/glycerol frozen solution; EPR spectroscopy was employed to confirm the identity of the trapped intermediate. (via Semantic Scholar)
UN Sustainable Development Goal Categories
6. Clean Water and Sanitation (OpenAlex)
Source: ORCID
Added: December 12, 2023

2006 journal article

Cytochrome P450 compound I

Journal of the American Chemical Society, 128(14), 4580–4581.

By: M. Newcomb*, R. Zhang*, R. Chandrasena*, J. Halgrimson*, J. Horner*, T. Makris*, S. Sligar*

Contributors: M. Newcomb*, R. Zhang*, R. Chandrasena*, J. Halgrimson*, J. Horner*, T. Makris*, S. Sligar*

TL;DR: Formation of the Compound I derivative of a P450 enzyme is reported by laser flash photolysis oxidation of the corresponding Compound II species, an iron(IV)-oxo neutral porphyrin intermediate. (via Semantic Scholar)
Source: ORCID
Added: December 12, 2023

2006 journal article

The status of high-valent metal oxo complexes in the P450 cytochromes

Journal of Inorganic Biochemistry, 100(4), 507–518.

By: T. Makris*, K. Koenig*, I. Schlichting* & S. Sligar*

Contributors: T. Makris*, K. Koenig*, I. Schlichting* & S. Sligar*

TL;DR: The current status of the isolation and characterization of the P450 oxo-Fe(IV) is examined and compared to analogous states in related heme enzymes, and the utilization of cofactor exchange to stabilize high-valent oxe-states in the P 450 is addressed. (via Semantic Scholar)
UN Sustainable Development Goal Categories
6. Clean Water and Sanitation (OpenAlex)
Source: ORCID
Added: December 12, 2023

2005 journal article

A retinoic acid binding cytochrome P450: CYP120A1 from Synechocystis sp. PCC 6803

Archives of Biochemistry and Biophysics, 436(1), 110–120.

By: N. Ke*, J. Baudry*, T. Makris*, M. Schuler* & S. Sligar*

Contributors: N. Ke*, J. Baudry*, T. Makris*, M. Schuler* & S. Sligar*

TL;DR: Homology modeling predictions of the three-dimensional structure of CYP120A1 coupled with in silico screening for potential substrates and experimental spectroscopic analyses have identified retinoic acid as a compound binding with high affinity to this P450's catalytic site. (via Semantic Scholar)
UN Sustainable Development Goal Categories
15. Life on Land (OpenAlex)
Source: ORCID
Added: December 12, 2023

2005 book

Activation of molecular oxygen by cytochrome P450

In Cytochrome P450: Structure, Mechanism, and Biochemistry: Third edition (pp. 149–182).

By: T. Makris*, I. Denisov*, I. Schlichting* & S. Sligar*

Contributors: T. Makris*, I. Denisov*, I. Schlichting* & S. Sligar*

Source: ORCID
Added: December 12, 2023

2005 journal article

Structure and chemistry of cytochrome P450

Chemical Reviews, 105(6), 2253–2277.

By: I. Denisov*, T. Makris*, S. Sligar* & I. Schlichting*

Contributors: I. Denisov*, T. Makris*, S. Sligar* & I. Schlichting*

TL;DR: This review will concentrate on findings with P-450cam of the Pseudomonas putida camphor-5-exo-hydroxylase, and attention will be drawn to parallel and contrasting examples from other P- 450s as appropriate. (via Semantic Scholar)
Source: ORCID
Added: December 12, 2023

2005 journal article

The influence of substrate on the spectral properties of oxyferrous wild-type and T252A cytochrome P450-CAM

Archives of Biochemistry and Biophysics, 436(1), 40–49.

By: M. Sono*, R. Perera*, S. Jin*, T. Makris*, S. Sligar*, T. Bryson*, J. Dawson*

Contributors: M. Sono*, R. Perera*, S. Jin*, T. Makris*, S. Sligar*, T. Bryson*, J. Dawson*

TL;DR: The present results indicate that the structures of the camphor analogs can sensitively influence the physical (spectroscopic) properties of the P450 dioxygen complex and could also affect its reactivity. (via Semantic Scholar)
Source: ORCID
Added: December 12, 2023

2005 journal article

Thirty years of microbial P450 monooxygenase research: Peroxo-heme intermediates - The central bus station in heme oxygenase catalysis

Biochemical and Biophysical Research Communications, 338(1), 346–354.

By: S. Sligar*, T. Makris* & I. Denisov*

Contributors: S. Sligar*, T. Makris* & I. Denisov*

TL;DR: This volume provides an opportunity to recognize the breakthroughs of the "Hayaishi School" and has been the prolific contributions of Professor Ishimura et al. (via Semantic Scholar)
Source: ORCID
Added: December 12, 2023

2003 journal article

Epoxidation of olefins by hydroperoxo-ferric cytochrome P450

Journal of the American Chemical Society, 125(12), 3406–3407.

By: S. Jin*, T. Makris*, T. Bryson*, S. Sligar* & J. Dawson*

Contributors: S. Jin*, T. Makris*, T. Bryson*, S. Sligar* & J. Dawson*

TL;DR: The present results provide strong evidence that hydroperoxo-ferric P450 can serve as a second electrophilic oxidant capable of olefin epoxidation. (via Semantic Scholar)
UN Sustainable Development Goal Categories
6. Clean Water and Sanitation (OpenAlex)
Source: ORCID
Added: December 12, 2023

2003 journal article

Haem-oxygen reactive intermediates: Catalysis by the two-step

Biochemical Society Transactions, 31(3), 516–519.

By: T. Makris*, I. Denisov* & S. Sligar*

Contributors: T. Makris*, I. Denisov* & S. Sligar*

TL;DR: The characterization of these intermediates by optical and EPR spectroscopies has reinforced the similarity of these intermediate states in a number of haem enzyme systems, and the reactivity in P450 and horseradish peroxidase provides a paradigm for many other haem enzymes. (via Semantic Scholar)
Source: ORCID
Added: December 12, 2023

2003 journal article

Resonance Raman Spectroscopic Studies of Hydroperoxo-Myoglobin at Cryogenic Temperatures

Journal of the American Chemical Society, 125(45), 13714–13718.

By: M. Ibrahim*, I. Denisov*, T. Makris*, J. Kincaid* & S. Sligar*

Contributors: M. Ibrahim*, I. Denisov*, T. Makris*, J. Kincaid* & S. Sligar*

UN Sustainable Development Goal Categories
7. Affordable and Clean Energy (OpenAlex)
Source: ORCID
Added: December 12, 2023

2002 article

Cryoradiolysis for the study of P450 reaction intermediates

Cytochrome P450 Part C, Vol. 357, pp. 103–115.

By: I. Denisov, T. Makris* & S. Sugar

Contributors: I. Denisov, T. Makris* & S. Sligar

TL;DR: This chapter describes cryoradiolysis for the study of p450 reaction intermediates, a method based on preparing the precursor at ambient conditions, freezing it at 77 K, and irradiating it with high-energy photons from a 6°C source. (via Semantic Scholar)
UN Sustainable Development Goal Categories
6. Clean Water and Sanitation (OpenAlex)
Source: ORCID
Added: December 12, 2023

2002 journal article

Formation and decay of hydroperoxo-ferric heme complex in horseradish peroxidase studied by cryoradiolysis

Journal of Biological Chemistry, 277(45), 42706–42710.

By: I. Denisov*, T. Makris* & S. Sligar*

Contributors: I. Denisov*, T. Makris* & S. Sligar*

Source: ORCID
Added: December 12, 2023

2002 journal article

Mechanistic enzymology of oxygen activation by the cytochromes P450

Drug Metabolism Reviews, 34(4), 691–708.

By: T. Makris*, R. Davydov*, I. Denisov*, B. Hoffman* & S. Sligar*

Contributors: T. Makris*, R. Davydov*, I. Denisov*, B. Hoffman* & S. Sligar*

TL;DR: The detailed mechanism of P450 dioxygen scission is discussed utilizing the CYP101 hydroxylation of camphor as a model system and a structural and spectroscopic analysis of the nature of critical intermediate states in the reaction is discussed. (via Semantic Scholar)
UN Sustainable Development Goal Categories
6. Clean Water and Sanitation (OpenAlex)
Source: ORCID
Added: December 12, 2023

2001 journal article

Cryotrapped Reaction Intermediates of Cytochrome P450 Studied by Radiolytic Reduction with Phosphorus-32

Journal of Biological Chemistry, 276(15), 11648–11652.

By: I. Denisov*, T. Makris* & S. Sligar*

Contributors: I. Denisov*, T. Makris* & S. Sligar*

TL;DR: The UV-visible optical spectra of the reduced oxygenated state of CYP101 are determined and it is shown that the primary intermediate, a hydroperoxo-P450, is stable below 180 K and converts smoothly to the product complex at ∼195 K and no spectral changes indicating the presence of oxoferryl species was observed. (via Semantic Scholar)
Source: ORCID
Added: December 12, 2023

2001 journal article

Hydroxylation of camphor by reduced oxy-cytochrome p450cam: Mechanistic implications of EPR and ENDOR studies of catalytic intermediates in native and mutant enzymes

Journal of the American Chemical Society, 123(7), 1403–1415.

By: R. Davydov*, T. Makris*, V. Kofman*, D. Werst*, S. Sligar* & B. Hoffman*

Contributors: R. Davydov*, T. Makris*, V. Kofman*, D. Werst*, S. Sligar* & B. Hoffman*

TL;DR: Chemical and EPR quantitations indicate the reaction pathway involving 5B yields 5-exo-hydroxycamphor quantitatively, and gamma-irradiation at cryogenic temperatures of the ternary complexes of camphor, dioxygen, and ferro-cytochrome P450cam uses EPR and ENDOR spectroscopies to characterize the primary product of reduction as well as subsequent states created by annealing reduced oxyP450. (via Semantic Scholar)
Source: ORCID
Added: December 12, 2023

1999 journal article

EPR and ENDOR of catalytic intermediates in cryoreduced native and mutant oxy-cytochromes P450cam: Mutation-induced changes in the proton delivery system [15]

Journal of the American Chemical Society, 121(45), 10654–10655.

By: R. Davydov*, I. Macdonald*, T. Makris*, S. Sugar & B. Hoffman*

Contributors: R. Davydov*, I. Macdonald*, T. Makris*, S. Sugar & B. Hoffman*

Source: ORCID
Added: December 12, 2023

Employment

Updated: October 27th, 2021 08:06

2020 - present

North Carolina State University Raleigh, North Carolina, US
Associate Professor Molecular and Structural Biochemistry

2012 - 2020

University of South Carolina Columbia, SC, US
Assistant Professor Chemistry and Biochemistry

Education

Updated: January 17th, 2015 12:13

2006 - 2012

University of Minnesota System Minneapolis, MN, US
Post-Doc Biochemistry Molecular Biology and Biophysics

2003 - 2006

University of Illinois System Urbana, IL, US
Post-doc Biochemistry

1997 - 2003

University of Illinois System Urbana, IL, US
Ph.D Center for Biophysics and Computational Biology

1992 - 1996

University of Pennsylvania Philadelphia, PA, US
B.A. Biology

Funding History

Funding history based on the linked ORCID record. Updated: October 27th, 2021 08:04

grant February 3, 2021 - September 30, 2025
Dioxygen-dependent mechanisms of hydrocarbon biosynthesis
National Institute of Food and Agriculture
grant September 20, 2019 - June 30, 2023
Divergence of Carboxylate-Bridged Diiron Enzymes for Natural Product Biosynthesis
National Institute of General Medical Sciences
grant August 15, 2018 - July 31, 2021
MRI: Acquisition of a High Resolution, Quadrupole Mass Spectrometer to Enable Research and Education at the Interface of Chemistry and Biology
Directorate for Mathematical & Physical Sciences
grant August 1, 2017 - July 31, 2020
In-situ polymerization to immobilize contaminants in groundwater
Directorate for Mathematical & Physical Sciences
grant May 1, 2016 - April 30, 2021
CAREER: Mechanism of Cytochrome P450 Alkene Biosynthesis
National Science Foundation - Directorate for Mathematical & Physical Sciences

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