Patents by Inventor John Ralph
John Ralph 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: 20260144255Abstract: A method to produce a mixture comprising poacic acid (X) and poacidiene (Y) and the resulting product-by-process. The method includes the steps of subjecting a solution of ferulic acid to a free-radical coupling reaction to yield an intermediate mixture comprising ferulic acid dehydrodimers and decarboxylating the intermediate mixture to yield a product mixture containing poacic acid (X) and poacidiene (Y).Type: ApplicationFiled: November 19, 2025Publication date: May 28, 2026Applicant: Wisconsin Alumni Research FoundationInventors: John Ralph, Fachuang Lu, Mehdi Kabbage
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Patent number: 12358939Abstract: A method of completely dissolving lignocellulosic biomass. The method includes the steps of dissolving a sample of biomass in an aqueous solution of strong acid and an amine-thiol to yield a first solution. A method for measuring lignin concentration in biomass via absorbance of the first solution at a wavelength of about 283 nm by comparing the measured absorbance to a standard curve of absorbance values made from solutions of known lignin concentration.Type: GrantFiled: June 9, 2022Date of Patent: July 15, 2025Assignee: Wisconsin Alumni Research FoundationInventors: Fachuang Lu, John Ralph
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Publication number: 20250059130Abstract: A method for producing paracetamol from renewable biological feedstocks. The method comprises isolating p-hydroxybenzoic acid (pHBA) or a mixture of pHBA and p-hydroxybenzamide (pHBAm) from biomass. One version of the method comprises converting pHBA to pHBAm, subsequently to p-aminophenol (pAmP), and subsequently to paracetamol. The yield can be increased by recycling unreacted pHBAm to feed into the amide to amine conversion step. In a second version of the method, the phenolic hydroxyl group of pHBA or pHBAm is first protected. The subsequent reactions proceed as noted, with deprotection as the last step.Type: ApplicationFiled: August 13, 2024Publication date: February 20, 2025Applicant: Wisconsin Alumni Research FoundationInventors: John Ralph, Steven Karlen, Vitaliy Timokhin, Canan Sener
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Publication number: 20240276985Abstract: Antimicrobial diferulates, compositions containing same, and uses of same for inhibiting growth of microorganisms. The antimicrobial diferulates can be used alone or in combination with other antimicrobial agents to inhibit growth of microorganisms such as fungi, oomycetes, and other microorganisms having a glucan-containing cell wall. The antimicrobial diferulates can be included in pharmaceutical compositions for treatment of animals or included in agricultural compositions for treatment of plants, crops, and soils.Type: ApplicationFiled: April 18, 2024Publication date: August 22, 2024Applicant: Wisconsin Alumni Research FoundationInventors: Jeff S. Piotrowski, Fachuang Lu, Mehdi Kabbage, John Ralph, Robert C. Landick
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Patent number: 11985974Abstract: Antimicrobial diferulates, compositions containing same, and uses of same for inhibiting growth of microorganisms. The antimicrobial diferulates can be used alone or in combination with other antimicrobial agents to inhibit growth of microorganisms such as fungi, oomycetes, and other microorganisms having a glucan-containing cell wall. The antimicrobial diferulates can be included in pharmaceutical compositions for treatment of animals or included in agricultural compositions for treatment of plants, crops, and soils.Type: GrantFiled: August 27, 2021Date of Patent: May 21, 2024Assignee: Wisconsin Alumni Research FoundationInventors: Jeff S. Piotrowski, Fachuang Lu, Mehdi Kabbage, John Ralph, Robert C. Landick
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Patent number: 11981904Abstract: The invention is directed to BAHD acyltransferase enzymes, nucleic acids encoding BAHD acyltransferase enzymes, and inhibitory nucleic acids adapted to inhibit the expression and/or translation of BAHD acyltransferase RNA; expression cassettes, plant cells, and plants that have or encode such nucleic acids and enzymes; and methods of making and using such nucleic acids, enzymes, expression cassettes, cells, and plants.Type: GrantFiled: November 8, 2019Date of Patent: May 14, 2024Assignees: Wisconsin Alumni Research Foundation, The University of British ColumbiaInventors: Steven D. Karlen, Rebecca Anne Smith, John Ralph, Emily Beebe, Craig Bingman, Brian Fox, Shawn Mansfield, Heather Mackay, Hoon Kim, Yaseen Mottiar, Faride Unda
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Patent number: 11807876Abstract: The invention is directed to p-coumaroyl-CoA:monolignol transferase enzymes, nucleic acids encoding p-coumaroyl-CoA:monolignol transferase enzymes, and inhibitory nucleic acids adapted to inhibit the expression and/or translation of p-coumaroyl-CoA:monolignol transferase RNA; expression cassettes, plant cells, and plants that have or encode such nucleic acids and enzymes; and methods of making and using such nucleic acids, enzymes, expression cassettes, cells, and plants.Type: GrantFiled: November 30, 2020Date of Patent: November 7, 2023Assignee: Wisconsin Alumni Research FoundationInventors: John Ralph, Steven D. Karlen, Rebecca Anne Smith, Brian Fox, Emily Beebe, Craig Bingman
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Patent number: 11807875Abstract: The invention relates to feruloyl-CoA:monolignol transferase enzymes and nucleic acids encoding the feruloyl-CoA:monolignol transferase enzymes. The enzymes and/or the nucleic acids enable incorporation of monolignol ferulates into the lignin of plants. The monolignol ferulates include, for example, p-coumaryl ferulate, coniferyl ferulate, and/or sinapyl ferulate.Type: GrantFiled: November 30, 2020Date of Patent: November 7, 2023Assignee: Wisconsin Alumni Research FoundationInventors: John Ralph, Steven D. Karlen, Rebecca Anne Smith, Brian Fox, Emily Beebe, Craig Bingman
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Publication number: 20230203461Abstract: The present application relates to nucleic acids encoding polypeptides with ?-etherase activity; polypeptides with ?-etherase activity; vectors comprising said nucleic acids for the production of recombinant ?-etherase; cells, for example microbial cells transformed with nucleic acids encoding ?-etherase activity and vectors, including nucleic acids encoding ?-etherases; a composition comprising ?-etherases suitable for processing lignocellulose and a method that uses ?-etherases or compositions comprising ?-etherases in the processing of lignocellulose and related polysaccharides.Type: ApplicationFiled: January 9, 2021Publication date: June 29, 2023Applicants: The University of York, Wisconsin Alumni Research FoundationInventors: Neil Bruce, Nicola Oates, John Ralph
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Publication number: 20220411453Abstract: A method of completely dissolving lignocellulosic biomass. The method includes the steps of dissolving a sample of biomass in an aqueous solution of strong acid and an amine-thiol to yield a first solution. A method for measuring lignin concentration in biomass via absorbance of the first solution at a wavelength of about 283 nm by comparing the measured absorbance to a standard curve of absorbance values made from solutions of known lignin concentration.Type: ApplicationFiled: June 9, 2022Publication date: December 29, 2022Inventors: Fachuang Lu, John Ralph
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Patent number: 11447754Abstract: Enzymes for depolymerizing lignin. The enzymes include dehydrogenases, ?-etherases, and glutathione lyases. The dehydrogenases can comprise one or more or LigD, LigO, LigN, and LigL. The ?-etherases can comprise one or more of LigE, LigF, LigP, and BaeA. The glutathione lyases can comprise any one or more of LigG and a number of non-stereospecific, optionally recombinant glutathione lyases derived from Sphingobium sp. SYK-6, Novosphingobium aromaticivorans, Escherichia coli, Streptococcus sanguinis, Phanerochaete chrysosporium, and other microorganisms. The enzymes can be combined in compositions and/or used in methods of processing lignin or other aromatic compounds in vitro.Type: GrantFiled: September 30, 2020Date of Patent: September 20, 2022Assignee: Wisconsin Alumni Research FoundationInventors: Timothy James Donohue, Daniel Leo Gall, Wayne S. Kontur, Hoon Kim, John Ralph, Daniel R. Noguera, Brian Fox, Craig Bingman
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Patent number: 11414372Abstract: Methods of detecting and, optionally, determining a level of incorporation of monolignol ester conjugates into lignin. The methods include derivatizing lignin to acylate at least a portion of free phenolic and aliphatic hydroxyls and to halogenate at least a portion of benzylic alcohols present in the lignin to yield derivatized lignin, treating the derivatized lignin with a reducing agent to cleave at least a portion of the derivatized lignin to yield lignin cleavage products, acetylating at least a portion of free hydroxyl groups in the lignin cleavage products with a labeled acetylation agent to yield labeled lignin fragments, and detecting the labeled lignin fragments.Type: GrantFiled: January 21, 2019Date of Patent: August 16, 2022Assignee: WISCONSIN ALUMNI RESEARCH FOUNDATIONInventors: John Ralph, Steven D Karlen, Fachuang Lu, Dharshana Padmakshan
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Patent number: 11326178Abstract: The invention relates to nucleic acids encoding a p-coumaroyl-CoA:monolignol transferase and to inhibitory nucleic acids adapted to inhibit the expression and/or translation of a p-coumaroyl-CoA:monolignol transferase RNA. Inhibition of p-coumaroyl-CoA:monolignol transferase in plants improves the incorporation of monolignol ferulates into the lignin of plants, giving rise to plant biomass that is more easily processed into useful products such as paper and biofuels.Type: GrantFiled: August 14, 2019Date of Patent: May 10, 2022Assignees: Wisconsin Alumni Research Foundation, Board of Trustees of Michigan State University, The Board of Trustees of Illinois State UniversityInventors: Curtis Wilkerson, John Ralph, Saunia Withers, John Sedbrook
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Publication number: 20220061321Abstract: Antimicrobial diferulates, compositions containing same, and uses of same for inhibiting growth of microorganisms. The antimicrobial diferulates can be used alone or in combination with other antimicrobial agents to inhibit growth of microorganisms such as fungi, oomycetes, and other microorganisms having a glucan-containing cell wall. The antimicrobial diferulates can be included in pharmaceutical compositions for treatment of animals or included in agricultural compositions for treatment of plants, crops, and soils.Type: ApplicationFiled: August 27, 2021Publication date: March 3, 2022Applicant: WISCONSIN ALUMNI RESEARCH FOUNDATIONInventors: Jeff S. Piotrowski, Fachuang Lu, Mehdi Kabbage, John Ralph, Robert C. Landick
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Publication number: 20220002744Abstract: The invention is directed to BAHD acyltransferase enzymes, nucleic acids encoding BAHD acyltransferase enzymes, and inhibitory nucleic acids adapted to inhibit the expression and/or translation of BAHD acyltransferase RNA; expression cassettes, plant cells, and plants that have or encode such nucleic acids and enzymes; and methods of making and using such nucleic acids, enzymes, expression cassettes, cells, and plants.Type: ApplicationFiled: November 8, 2019Publication date: January 6, 2022Applicants: WISCONSIN ALUMNI RESEARCH FOUNDATION, THE UNIVERSITY OF BRITISH COLUMBIAInventors: Steven D. Karlen, Rebecca Anne Smith, John Ralph, Emily Beebe, Craig Bingman, Brian Fox, Shawn Mansfield, Heather Mackay, Hoon Kim, Yaseen Mottiar, Faride Unda
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Patent number: 11186882Abstract: A method of liquefying biomass. The method includes the steps of contacting biomass with a solution comprising an acyl halide and an acid; and then contacting the biomass with a reductant.Type: GrantFiled: July 23, 2019Date of Patent: November 30, 2021Assignee: Wisconsin Alumni Research FoundationInventors: Steven D. Karlen, John Ralph
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Publication number: 20210207104Abstract: The invention relates to feruloyl-CoA:monolignol transferase enzymes and nucleic acids encoding the feruloyl-CoA:monolignol transferase enzymes. The enzymes and/or the nucleic acids enable incorporation of monolignol ferulates into the lignin of plants. The monolignol ferulates include, for example, p-coumaryl ferulate, coniferyl ferulate, and/or sinapyl ferulate.Type: ApplicationFiled: November 30, 2020Publication date: July 8, 2021Applicant: WISCONSIN ALUMNI RESEARCH FOUNDATIONInventors: John Ralph, Steven D. Karlen, Rebecca Anne Smith, Brian Fox, Emily Beebe, Craig Bingman
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Publication number: 20210095263Abstract: The invention is directed to p-coumaroyl-CoA:monolignol transferase enzymes, nucleic acids encoding p-coumaroyl-CoA:monolignol transferase enzymes, and inhibitory nucleic acids adapted to inhibit the expression and/or translation of p-coumaroyl-CoA:monolignol transferase RNA; expression cassettes, plant cells, and plants that have or encode such nucleic acids and enzymes; and methods of making and using such nucleic acids, enzymes, expression cassettes, cells, and plants.Type: ApplicationFiled: November 30, 2020Publication date: April 1, 2021Applicant: WISCONSIN ALUMNI RESEARCH FOUNDATIONInventors: John Ralph, Steven D. Karlen, Rebecca Anne Smith, Brian Fox, Emily Beebe, Craig Bingman
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Publication number: 20210095265Abstract: Enzymes for depolymerizing lignin. The enzymes include dehydrogenases, ?-etherases, and glutathione lyases. The dehydrogenases can comprise one or more or LigD, LigO, LigN, and LigL. The ?-etherases can comprise one or more of LigE, LigF, LigP, and BaeA. The glutathione lyases can comprise any one or more of LigG and a number of non-stereospecific, optionally recombinant glutathione lyases derived from Sphingobium sp. SYK-6, Novosphingobium aromaticivorans, Escherichia coli, Streptococcus sanguinis, Phanerochaete chrysosporium, and other microorganisms. The enzymes can be combined in compositions and/or used in methods of processing lignin or other aromatic compounds in vitro.Type: ApplicationFiled: September 30, 2020Publication date: April 1, 2021Applicant: WISCONSIN ALUMNI RESEARCH FOUNDATIONInventors: Timothy James Donohue, Daniel Leo Gall, Wayne S. Kontur, Hoon Kim, John Ralph, Daniel R. Noguera, Brian Fox, Craig Bingman
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Patent number: 10883090Abstract: The invention is directed to p-coumaroyl-CoA:monolignol transferase enzymes, nucleic acids encoding p-coumaroyl-CoA:monolignol transferase enzymes, and inhibitory nucleic acids adapted to inhibit the expression and/or translation of p-coumaroyl-CoA:monolignol transferase RNA; expression cassettes, plant cells, and plants that have or encode such nucleic acids and enzymes; and methods of making and using such nucleic acids, enzymes, expression cassettes, cells, and plants.Type: GrantFiled: April 18, 2018Date of Patent: January 5, 2021Assignee: WISCONSIN ALUMNI RESEARCH FOUNDATIONInventors: John Ralph, Steven D. Karlen, Rebecca Anne Smith, Brian Fox, Emily Beebe, Craig Bingman