Patents by Inventor F. Dean Toste
F. Dean Toste has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Publication number: 20250206708Abstract: The present disclosure features compounds (e.g., oxaziridine-based compounds), as well as related compositions and methods of use thereof, e.g., for selectively labeling a methionine residue in a target peptide or protein.Type: ApplicationFiled: March 28, 2023Publication date: June 26, 2025Inventors: F. Dean Toste, Christopher J. Chang, Audrey Reeves, Angel Gonzalez-valero, Patrick J. Moon, Edward Miller, Richard Alan Lewis, Yipin Lu, Jeffrey M. McKenna
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Publication number: 20240316223Abstract: A redox-based strategy for bioconjugation of tryptophan uses oxaziridine reagents that mimic oxidative cyclization reactions in indole-based alkaloid biosynthetic pathways to achieve highly selective and rapid tryptophan labeling.Type: ApplicationFiled: June 1, 2024Publication date: September 26, 2024Applicant: The Regents of the University of CaliforniaInventors: Patrick J. Moon, Xaio Xie, F. Dean Toste, Christopher J. Chang
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Patent number: 11353463Abstract: Chemoselective conjugation is achieved through redox reactivity by reacting an N-transfer oxidant with a thioether substrate in a redox reaction in an aqueous environment to form a conjugation product. In embodiments, Redox-Activated Chemical Tagging (ReACT) strategies for methionine-based protein functionalization. Oxaziridine (Ox) compounds serve as oxidant-mediated reagents for direct functionalization by converting methionine to the corresponding sulfimide conjugation product.Type: GrantFiled: May 2, 2019Date of Patent: June 7, 2022Assignee: The Regents of the University of CaliforniaInventors: ShiXian Lin, XiaoYu Yang, F. Dean Toste, Christopher J. Chang
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Patent number: 11332482Abstract: Au(III) complexes for [18F] trifluoromethylation and methods for producing the same are disclosed. A gold complex comprises Au(CF3)2LR, wherein L comprises a solubility supporting ligand and R comprises an organic substituent. The Au(III) complex can be used to prepare a positron emitting isotope that can be used as tracers for positron emitting tomography (PET) scans.Type: GrantFiled: May 21, 2018Date of Patent: May 17, 2022Assignee: THE REGENTS OF THE UNIVERSITY OF CALIFORNIAInventors: F. Dean Toste, Mark Daniel Levin, James Patrick O'Neil
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Patent number: 11155530Abstract: Chemoselective conjugation is achieved through redox reactivity by reacting an N-transfer oxidant with a thioether substrate in a redox reaction in an aqueous environment to form a conjugation product. In embodiments, Redox-Activated Chemical Tagging (ReACT) strategies for methionine-based protein functionalization. Oxaziridine (Ox) compounds serve as oxidant-mediated reagents for direct functionalization by converting methionine to the corresponding sulfimide conjugation product.Type: GrantFiled: February 1, 2021Date of Patent: October 26, 2021Assignee: The Regents of the University of CaliforniaInventors: Christopher J. Chang, F. Dean Toste, Alec H. Christian, Patti Zhang
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Publication number: 20210155600Abstract: Chemoselective conjugation is achieved through redox reactivity by reacting an N-transfer oxidant with a thioether substrate in a redox reaction in an aqueous environment to form a conjugation product. In embodiments, Redox-Activated Chemical Tagging (ReACT) strategies for methionine-based protein functionalization. Oxaziridine (Ox) compounds serve as oxidant-mediated reagents for direct functionalization by converting methionine to the corresponding sulfimide conjugation product.Type: ApplicationFiled: February 1, 2021Publication date: May 27, 2021Applicant: The Regents of the University of CaliforniaInventors: Christopher J. Chang, F. Dean Toste, Alec H. Christian, Patti Zhang
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Publication number: 20200172557Abstract: Au(III) complexes for [18F] trifluoromethylation and methods for producing the same are disclosed. A gold complex comprises Au(CF3)2LR, wherein L comprises a solubility supporting ligand and R comprises an organic substituent. The Au(III) complex can be used to prepare a positron emitting isotope that can be used as tracers for positron emitting tomography (PET) scans.Type: ApplicationFiled: May 21, 2018Publication date: June 4, 2020Inventors: F. Dean Toste, Mark Daniel Levin, James Patrick O'Neil
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Patent number: 10618856Abstract: Provided herein are methods for producing cyclic and acyclic ketones from trimerization and dimerization of alkyl ketones, including for example methyl ketones. Such cyclic and acyclic ketones may be suitable for use as fuel and lubricant precursors, and may be hydrodeoxygenated to form their corresponding cycloalkanes and alkanes. Such cycloalkanes and alkanes may be suitable for use as fuels, including jet fuels, and lubricants.Type: GrantFiled: December 18, 2018Date of Patent: April 14, 2020Assignees: The Regents of the University of California, BP Corporation North America Inc.Inventors: Sanil Sreekumar, F. Dean Toste, Amit A. Gokhale, Gorkem Gunbas, Balakrishnan Madhesan, Alexis T. Bell, Eric Sacia, George E. Arab
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Publication number: 20190257838Abstract: Chemoselective conjugation is achieved through redox reactivity by reacting an N-transfer oxidant with a thioether substrate in a redox reaction in an aqueous environment to form a conjugation product. In embodiments, Redox-Activated Chemical Tagging (ReACT) strategies for methionine-based protein functionalization. Oxaziridine (Ox) compounds serve as oxidant-mediated reagents for direct functionalization by converting methionine to the corresponding sulfimide conjugation product.Type: ApplicationFiled: May 2, 2019Publication date: August 22, 2019Applicant: The Regents of the University of CaliforniaInventors: ShiXian Lin, XiaoYu Yang, F. Dean Toste, Christopher J. Chang
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Patent number: 10207961Abstract: Provided herein are methods for producing cyclic and acyclic ketones from trimerization and dimerization of alkyl ketones, including for example methyl ketones. Such cyclic and acyclic ketones may be suitable for use as fuel and lubricant precursors, and may be hydrodeoxygenated to form their corresponding cycloalkanes and alkanes. Such cycloalkanes and alkanes may be suitable for use as fuels, including jet fuels, and lubricants.Type: GrantFiled: March 23, 2015Date of Patent: February 19, 2019Assignees: The Regents of the University of California, BP Corporation North America Inc.Inventors: Sanil Sreekumar, F. Dean Toste, Amit A. Gokhale, Gorkem Gunbas, Balakrishnan Madhesan, Alexis T. Bell, Eric Sacia, George E. Arab
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Patent number: 10138193Abstract: Provided herein are methods for producing ?,?-unsaturated ketones from the condensation of methyl ketones in the presence of an amine catalyst. Such amine catalysts may be supported, for example, on a silica-alumina support. Such amine catalysts may be used in the presence of an additional acid. The ?,?-unsaturated ketones may be produced by dimerization and/or timerization of the methyl ketones. Such ?,?-unsaturated ketones may be suitable for use in producing fuels, gasoline additives, and/or lubricants, or precursors thereof. The methyl ketones may be obtained from renewable sources, such as by the fermentation of biomass.Type: GrantFiled: October 28, 2015Date of Patent: November 27, 2018Assignees: The Regents of the University of California, BP Corporation North America Inc.Inventors: Shylesh Sankaranarayanapillai, Sanil Sreekumar, F. Dean Toste, Alexis T. Bell, Amit A. Gokhale, Adam Grippo, George E. Arab
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Patent number: 10106480Abstract: Provided herein are methods for producing ketone(s) from the condensation of methyl ketone(s) and alcohol(s) in the presence of an amine catalyst and a metal catalyst. Such amine catalysts may be supported, for example, on a silica-alumina support. Such ketones may be suitable for use in producing fuels, gasoline additives, and/or lubricants, or precursors thereof. The methyl ketone(s) and/or alcohol(s) may be obtained from renewable sources, such as by fermentation of biomass.Type: GrantFiled: October 28, 2015Date of Patent: October 23, 2018Assignees: The Regents of the University of California, BP Corporation North America Inc.Inventors: Shylesh Sankaranarayanapillai, Sanil Sreekumar, F. Dean Toste, Alexis T. Bell, Amit A. Gokhale, Adam Grippo
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Patent number: 9981977Abstract: The discovery of distinct modes of asymmetric catalysis has the potential to rapidly advance chemists' ability to build enantioenriched molecules. As an example, the use of chiral cation salts as phase-transfer catalysts for anionic reagents has enabled a vast set of enantioselective transformations. A largely overlooked analogous mechanism wherein a chiral anionic catalyst brings a cationic species into solution is itself a powerful method. The concept is broadly applicable to a number of different reaction pathways, including to the enantioselective fluorocyclization of olefins, and dearomatization of aromatic systems with a cationic electrophile-transferring (e.g., fluorinating) agent and a chiral phosphate catalyst. The reactions proceed in high yield and stereoselectivity. The compounds and methods of the invention are of particular value, especially considering the scarcity of alternative approaches.Type: GrantFiled: December 26, 2012Date of Patent: May 29, 2018Assignee: THE REGENTS OF THE UNIVERSITY OF CALIFORNIAInventors: Vivek Rauniyar, Aaron D. Lackner, Gregory L. Hamilton, F. Dean Toste, Robert J. Phipps, Hunter Shunatona, Natalja Frueh, Yiming Wang, Jeffrey Wu, Jigar Patel, Takashi Honjo
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Patent number: 9856427Abstract: The present disclosure provides methods to produce ketones suitable for use as fuels and lubricants by catalytic conversion of an acetone-butanol-ethanol (ABE) fermentation product mixture that can be derived from biomass.Type: GrantFiled: April 26, 2012Date of Patent: January 2, 2018Assignees: The Regents of the University of California, BP Corporation North America Inc.Inventors: F. Dean Toste, Pazhamalai Anbarasan, Joseph B. Binder, Paul A. Willems, Douglas S. Clark, Zach Baer, Sanil Sreekumar, Harvey W. Blanch
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Patent number: 9790444Abstract: The present disclosure generally relates to the catalytic conversion of alcohols into hydrocarbon ketones suitable for use as fuels. More specifically, the present disclosure relates to the catalytic conversion of a mixture of isopropanol-butanol-ethanol (IBE) or acetone-butanol-ethanol (ABE), into ketones suitable for use as fuels. The ABE or IBE mixtures may be obtained from the fermentation of biomass or sugars.Type: GrantFiled: April 25, 2014Date of Patent: October 17, 2017Assignees: The Regents of the University of California, BP Corporation North America Inc.Inventors: Zachary C. Baer, Harvey W. Blanch, Douglas S. Clark, Sanil Sreekumar, F. Dean Toste, Gorkem Gunbas, Konstantinos A. Goulas, Amit A. Gokhale, Joseph B. Binder
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Patent number: 9738617Abstract: The present disclosure generally relates to the production of fuels, gasoline additives, and/or lubricants, and precursors thereof. The compounds used to produce the fuels, gasoline additives, and/or lubricants, and precursors thereof may be derived from biomass. The fuels, gasoline additives, and/or lubricants, and precursors thereof may be produced by a combination of intermolecular and/or intramolecular aldol condensation reactions, Guerbet reactions, hydrogenation reactions, and/or oligomerization reactions.Type: GrantFiled: June 3, 2014Date of Patent: August 22, 2017Assignees: The Regents of the University of California, BP Corporation North America Inc.Inventors: Eric Sacia, Anbarasan Pazhamalai, Balakrishnan Madhesan, Sanil Sreekumar, F. Dean Toste, Amit A. Gokhale, Martin E. Carrera, Alexis T. Bell, Gorkem Gunbas
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Patent number: 9403854Abstract: The invention pertains to the use of Group 8 transition metal carbene complexes as catalysts for olefin cross-metathesis reactions. In particular, ruthenium and osmium alkylidene complexes substituted with an N-heterocyclic carbene ligand are used to catalyze cross-metathesis reactions to provide a variety of substituted and functionalized olefins, including phosphonate-substituted olefins, directly halogenated olefins, 1,1,2-trisubstituted olefins, and quaternary allylic olefins. The invention further provides a method for creating functional diversity using the aforementioned complexes to catalyze cross-metathesis reactions of a first olefinic reactant, which may or may not be substituted with a functional group, with each of a plurality of different olefinic reactants, which may or may not be substituted with functional groups, to give a plurality of structurally distinct olefinic products.Type: GrantFiled: October 16, 2013Date of Patent: August 2, 2016Assignee: CALIFORNIA INSTITUTE OF TECHNOLOGYInventors: Robert H. Grubbs, Arnab K. Chatterjee, Tae-Lim Choi, Steven D. Goldberg, Jennifer A. Love, John P. Morgan, Daniel P. Sanders, Matthias Scholl, F. Dean Toste, Tina M. Trnka
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Publication number: 20140350253Abstract: The discovery of distinct modes of asymmetric catalysis has the potential to rapidly advance chemists' ability to build enantioenriched molecules. As an example, the use of chiral cation salts as phase-transfer catalysts for anionic reagents has enabled a vast set of enantioselective transformations. A largely overlooked analogous mechanism wherein a chiral anionic catalyst brings a cationic species into solution is itself a powerful method. The concept is broadly applicable to a number of different reaction pathways, including to the enantioselective fluorocyclization of olefins, and dearomatization of aromatic systems with a cationic electrophile-transferring (e.g., fluorinating) agent and a chiral phosphate catalyst. The reactions proceed in high yield and stereoselectivity. The compounds and methods of the invention are of particular value, especially considering the scarcity of alternative approaches.Type: ApplicationFiled: December 26, 2012Publication date: November 27, 2014Applicant: The Regents Of The University Of CaliforniaInventors: Vivek Rauniyar, Aaron D. Lackner, Gregory L. Hamilton, F. Dean Toste, Robert J. Phipps, Hunter Shunatona, Natalja Frueh, Yiming Wang, Jeffrey Wu, Jigar Patel, Takashi Honjo
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Publication number: 20140137465Abstract: The present disclosure provides methods to produce ketones suitable for use as fuels and lubricants by catalytic conversion of an acetone-butanol-ethanol (ABE) fermentation product mixture that can be derived from biomass.Type: ApplicationFiled: April 26, 2012Publication date: May 22, 2014Applicants: BP Corporation North America Inc., The Regents of the Universtiy of CaliforniaInventors: F. Dean Toste, Pazhamalai Anbarasan, Joseph B. Binder, Paul A. Willems, Douglas S. Clark, Zach Baer, Sanil Sreekumar, Harvey W. Blanch
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Patent number: 7262315Abstract: Methods are provided for carrying out nucleophilic addition reactions using oxo, sulfido or amido complexes of transition metals as reaction catalysts. Exemplary catalysts are oxo complexes of Group 7 transition metals, with rhenium (V) oxo complexes, including dioxo complexes, preferred. Nucleophilic addition reactions that can be catalyzed using the present methods include silylation, hydrosilylation, hydroamination, silylmetalation, carbometalation, aldol reactions, hydro- and carbometalation initiated cyclization/polymerization, and epoxide/aziridine opening. The invention also pertains to novel transition metal complexes that have utility in catalyzing such reactions.Type: GrantFiled: May 21, 2002Date of Patent: August 28, 2007Assignee: California Institute of TechnologyInventors: Robert H. Grubbs, F. Dean Toste