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Method for producing 3-hydroxypropionic acid and other products

Patent ·
OSTI ID:1489753

This invention relates to metabolically engineered microorganism strains, such as bacterial strains, in which there is an increased utilization of malonyl-CoA for production of a chemical product, which includes 3-hydroxypropionic acid.

Research Organization:
Cargill, Incorporated, Wayzata, MN (United States)
Sponsoring Organization:
USDOE
DOE Contract Number:
AR0000088
Assignee:
Cargill, Incorporated (Wayzata, MN)
Patent Number(s):
10,100,342
Application Number:
15/167,439
OSTI ID:
1489753
Country of Publication:
United States
Language:
English

References (153)

On the Role of Helix 0 of the Tryptophan Synthetase α Chain of Escherichia coli journal June 1996
Unprecedented acetoacetyl-coenzyme A synthesizing enzyme of the thiolase superfamily involved in the mevalonate pathway journal June 2010
A new perspective on thiamine catalysis journal August 2004
Rapid dissection of a complex phenotype through genomic-scale mapping of fitness altering genes journal May 2010
ZrOCl2·8H2O: An Efficient, Cheap and Reusable Catalyst for the Esterification of Acrylic Acid and Other Carboxylic Acids with Equimolar Amounts of Alcohols journal April 2006
The tyrosine repressor negatively regulates aroH expression in Escherichia coli. journal June 1991
Structure–function analysis of NADPH:nitrate reductase from Aspergillus nidulans: analysis of altered pyridine nucleotide specificity in vivo journal June 2000
Mycobacterium tuberculosis appears to lack α-ketoglutarate dehydrogenase and encodes pyruvate dehydrogenase in widely separated genes: Pyruvate dehydrogenase of Mycobacterium tuberculosis journal June 2005
Lactate-Utilizing Bacteria, Isolated from Human Feces, That Produce Butyrate as a Major Fermentation Product journal October 2004
Expression of proteins encoded by the Escherichia coli cyn operon: carbon dioxide-enhanced degradation of carbonic anhydrase. journal September 1994
Directed Evolution of Toluene ortho-Monooxygenase for Enhanced 1-Naphthol Synthesis and Chlorinated Ethene Degradation journal January 2002
De novo biosynthetic pathways: rational design of microbial chemical factories journal October 2008
Switch of coenzyme specificity of p -hydroxybenzoate hydroxylase 1 1Edited by A. R. Fersht journal September 1999
Monofunctional chorismate mutase from Bacillus subtilis: purification of the protein, molecular cloning of the gene, and overexpression of the gene product in Escherichia coli journal January 1990
Induction of specific base-pair substitutions in E. coli trpA mutants by chloroenthylene oxide, a carcinogenic vinyl chloride metabolite journal November 1985
A Physiology Study of Escherichia coli Overexpressing Phosphoenolpyruvate Carboxykinase journal April 2008
Binding of Two Flaviolin Substrate Molecules, Oxidative Coupling, and Crystal Structure of Streptomyces coelicolor A3(2) Cytochrome P450 158A2 journal January 2005
Top Value Added Chemicals from Biomass: Volume I -- Results of Screening for Potential Candidates from Sugars and Synthesis Gas report August 2004
Practical limits of function prediction journal January 2000
Extractive recovery of products from fermentation broths journal April 1999
A process for microbial hydrocarbon synthesis: Overproduction of fatty acids in Escherichia coli and catalytic conversion to alkanes journal June 2010
Aminotransferases: demonstration of homology and division into evolutionary subgroups journal June 1993
Conversion of a β-Ketoacyl Synthase to a Malonyl Decarboxylase by Replacement of the Active-Site Cysteine with Glutamine journal September 1999
Reactions of β-lactones with potassium alkoxides and their complexes with 18-crown-6 in aprotic solvents journal July 1993
Diversion of the Metabolic Flux from Pyruvate Dehydrogenase to Pyruvate Oxidase Decreases Oxidative Stress during Glucose Metabolism in Nongrowing Escherichia coli Cells Incubated under Aerobic, Phosphate Starvation Conditions journal October 2004
Enzymatic Conversion of β-Hydroxypropionate to Malonic Semialdehyde journal July 1959
Inhibitory activity spectrum of reuterin produced by Lactobacillus reuteri against intestinal bacteria journal January 2007
In vitro mutagenesis and overexpression of the Escherichia coli trpA gene and the partial characterization of the resultant tryptophan synthase mutant alpha-subunits. journal December 1986
Catalytic Plasticity of Fatty Acid Modification Enzymes Underlying Chemical Diversity of Plant Lipids journal November 1998
Effect of process parameters on 3-hydroxypropionic acid production from glycerol using a recombinant Escherichia coli journal April 2009
Cloning of the two pyruvate kinase isoenzyme structural genes from Escherichia coli: the relative roles of these enzymes in pyruvate biosynthesis. journal October 1995
Cloning and sequencing of Escherichia coli ubiC and purification of chorismate lyase. journal August 1992
Genome shuffling of Lactobacillus for improved acid tolerance journal July 2002
Challenges in Engineering Microbes for Biofuels Production journal February 2007
Development and evaluation of efficient recombinant Escherichia coli strains for the production of 3-hydroxypropionic acid from glycerol journal January 2009
Variant tricarboxylic acid cycle in Mycobacterium tuberculosis: Identification of α-ketoglutarate decarboxylase journal July 2005
The Enoyl-[Acyl-Carrier-Protein] Reductase (FabI) of Escherichia coli, which Catalyzes a Key Regulatory Step in Fatty Acid Biosynthesis, Accepts NADH and NADPH as Cofactors and is Inhibited by Palmitoyl-CoA journal December 1996
Synthesis of labeled acrylamide andN-methylolacrylamide (NMA):15N-acrylamide,13C-NMA,15N-NMA, and13C,15N-NMA journal January 2005
Malonyl-Coenzyme A Reductase from Chloroflexus aurantiacus, a Key Enzyme of the 3-Hydroxypropionate Cycle for Autotrophic CO2 Fixation journal May 2002
Organic acid toxicity, tolerance, and production in Escherichia coli biorefining applications journal August 2005
Fermentation of Glucose to Lactic Acid Coupled with Reactive Extraction:  A Review journal September 2004
Selective production of L-aspartic acid and L-phenylalanine by coupling reactions of aspartase and aminotransferase in Escherichia coli journal July 2000
Enoyl-Acyl Carrier Protein Reductase ( fabI ) Plays a Determinant Role in Completing Cycles of Fatty Acid Elongation in Escherichia coli journal November 1995
Effect of Overexpression of Actinobacillus succinogenes Phosphoenolpyruvate Carboxykinase on Succinate Production in Escherichia coli journal February 2004
Genetic and biochemical analyses of pantothenate biosynthesis in Escherichia coli and Salmonella typhimurium. journal January 1982
Molecular Iodine in Ionic Liquid: A Green Catalytic System for Esterification and Transesterification journal May 2010
Prediction of protein function from protein sequence and structure journal January 1999
Beta-alanine synthesis in Escherichia coli. journal January 1980
A mild and efficient method for esterification and transesterification catalyzed by iodine journal January 2002
A core catalytic domain of the TyrA protein family: arogenate dehydrogenase from Synechocystis journal August 2004
DNA shuffling of a family of genes from diverse species accelerates directed evolution journal January 1998
Inverse metabolic engineering: A strategy for directed genetic engineering of useful phenotypes journal July 2002
Engineered ketol-acid reductoisomerase and alcohol dehydrogenase enable anaerobic 2-methylpropan-1-ol production at theoretical yield in Escherichia coli journal May 2011
Overexpression, Purification, and Characterization of Tyrosine-Sensitive 3-Deoxy-d-arabino-heptulosonic Acid 7-Phosphate Synthase fromEscherichia coli journal March 1997
Melamine Deaminase and Atrazine Chlorohydrolase: 98 Percent Identical but Functionally Different journal April 2001
Methionine Biosynthesis in Escherichia coli and Corynebacterium glutamicum book January 2006
Nucleotide sequence of the adi gene, which encodes the biodegradative acid-induced arginine decarboxylase of Escherichia coli. journal March 1993
Application of Functional Genomics to Pathway Optimization for Increased Isoprenoid Production journal March 2008
The ARO4 gene of Candida albicans encodes a tyrosine-sensitive DAHP synthase: evolution, functional conservation and phenotype of Aro3p-, Aro4p-deficient mutants journal May 2002
Identification of PhoB binding sites of the yibD and ytfK promoter regions in Escherichia coli journal April 2011
Characterization of the hca Cluster Encoding the Dioxygenolytic Pathway for Initial Catabolism of 3-Phenylpropionic Acid in Escherichia coliK-12 journal June 1998
Autotrophic CO2 Fixation by Chloroflexus aurantiacus: Study of Glyoxylate Formation and Assimilation via the 3-Hydroxypropionate Cycle journal July 2001
Simultaneous synthesis of enantiomerically pure (S)-amino acids and (R)-amines using coupled transaminase reactions journal January 2003
?-hydroxypropionic acid production by Byssochlamys sp. grown on acrylic acid journal November 1993
Metabolic engineering of aromatic group amino acid pathway in Bacillus subtilis for L-phenylalanine production journal November 2004
Developments in Directed Evolution for Improving Enzyme Functions journal August 2007
Construction of an Escherichia coli K-12 Mutant for Homoethanologenic Fermentation of Glucose or Xylose without Foreign Genes journal January 2007
Menaquinone (vitamin K2) biosynthesis: overexpression, purification, and characterization of a new isochorismate synthase from Escherichia coli. journal May 1997
Cloning and Overexpression in Soluble Form of Functional Shikimate Kinase and 5-Enolpyruvylshikimate 3-Phosphate Synthase Enzymes from Mycobacterium tuberculosis journal August 2001
Sequencing and overexpression of the Escherichia coli aroE gene encoding shikimate dehydrogenase journal January 1988
The Rut Pathway for Pyrimidine Degradation: Novel Chemistry and Toxicity Problems journal April 2010
Engineering a mevalonate pathway in Escherichia coli for production of terpenoids journal June 2003
Semi-rational approaches to engineering enzyme activity: combining the benefits of directed evolution and rational design journal August 2005
Directed evolution of RuBisCO hypermorphs through genetic selection in engineered E.coli journal January 2006
Engineering of a functional human NADH-dependent cytochrome P450 system journal January 2001
Changes in the Intracellular Concentration of Acetyl-CoA and Malonyl-CoA in Relation to the Carbon and Energy Metabolism of Escherichia coli K12 journal August 1988
Toward a science of metabolic engineering journal June 1991
Improving cellular malonyl-CoA level in Escherichia coli via metabolic engineering journal May 2009
Inhibiting Bacterial Fatty Acid Synthesis journal April 2006
Sequences of the envM gene and of two mutated alleles in Escherichia coli journal October 1992
Enoyl Coenzyme A Hydratase (Crotonase) journal August 1972
Purification and characterization of 2-oxoglutarate decarboxylase of Leuconostoc oenos journal August 1990
Enzymes of a novel autotrophic CO2 fixation pathway in the phototrophic bacterium Chloroflexus aurantiacus, the 3-hydroxypropionate cycle journal August 1993
A novel methodology employing Corynebacterium glutamicum genome information to generate a new L -lysine-producing mutant journal January 2002
The overexpression, purification and complete amino acid sequence of chorismate synthase from Escherichia coli K12 and its comparison with the enzyme from Neurospora crassa journal April 1988
Molecular breeding of carotenoid biosynthetic pathways journal July 2000
Control Mechanisms in the Synthesis of Saturated Fatty Acids journal June 1977
A "Silent" Polymorphism in the MDR1 Gene Changes Substrate Specificity journal January 2007
A genomics approach to improve the analysis and design of strain selections journal May 2008
Characterization of the major promoter for the plasmid-encoded sucrose genes scrY, scrA, and scrB. journal December 1991
Identification and cloning of the Mycobacterium avium folA gene, required for dihydrofolate reductase activity journal November 1997
Light-directed, spatially addressable parallel chemical synthesis journal February 1991
Inhibition of Escherichia coli growth by acetic acid: a problem with methionine biosynthesis and homocysteine toxicity journal July 2002
A T42M Substitution in Bacterial 5-Enolpyruvylshikimate-3-phosphate Synthase (EPSPS) Generates Enzymes with Increased Resistance to Glyphosate journal January 2003
Human Catechol-O-Methyltransferase Haplotypes Modulate Protein Expression by Altering mRNA Secondary Structure journal December 2006
Improving lycopene production in Escherichia coli by engineering metabolic control journal May 2000
Thermal regulation of membrane lipid fluidity in bacteria journal February 1983
A New Enzymatic Method of Acrylamide Production journal May 1982
Polypeptide Release Factors in Prokaryotes and Eukaryotes journal January 2002
Sequence and overexpression of the menD gene from Escherichia coli. journal August 1989
Engineering Central Metabolic Pathways for High-Level Flavonoid Production in Escherichia coli journal April 2007
Exploring the diversity of complex metabolic networks journal December 2004
The qmeA (ts) mutation of Escherichia coli is localized in the fabI gene, which encodes enoyl-ACP reductase journal January 1996
A Novel Quinone-forming Monooxygenase Family Involved in Modification of Aromatic Polyketides journal February 2005
Cloning, crystallization and preliminary characterization of a β-carbonic anhydrase from Escherichia coli journal September 2000
3-phenylpropionate catabolism and the Escherichia coli oxidative stress response journal April 2005
Oxidation of Cysteine 645 of Cobalamin-Independent Methionine Synthase Causes a Methionine Limitation in Escherichia coli journal March 2009
Structure−Cytoprotective Activity Relationship of Simple Molecules Containing an α,β-Unsaturated Carbonyl System journal June 1997
Mutational analysis of the catalytic and feedback sites of the tryptophan-sensitive 3-deoxy-D-arabino-heptulosonate-7-phosphate synthase of Escherichia coli. journal December 1988
The Lysine Decarboxylase CadA Protects Escherichia coli Starved of Phosphate against Fermentation Acids journal January 2007
Structure of the EntB Multidomain Nonribosomal Peptide Synthetase and Functional Analysis of Its Interaction with the EntE Adenylation Domain journal April 2006
Genes restoring redox balance in fermentation-deficient E. coli NZN111 journal November 2009
Interdomain Communication between the Thiolation and Thioesterase Domains of EntF Explored by Combinatorial Mutagenesis and Selection journal August 2006
Role of bicarbonate/CO2 in the inhibition of Escherichia coli growth by cyanate. journal June 1995
Silent Polymorphisms Speak: How They Affect Pharmacogenomics and the Treatment of Cancer journal October 2007
Nucleotide sequence of the Escherichia coli cad operon: a system for neutralization of low extracellular pH. journal April 1992
Network rigidity and metabolic engineering in metabolite overproduction journal June 1991
Structure of Cellulases and Their Applications journal April 1997
Polyphosphate Kinase Protects Salmonella enterica from Weak Organic Acid Stress journal April 2005
Biorefineries:  Current Status, Challenges, and Future Direction journal July 2006
Genetic Evidence for an Interaction of the UbiG O-Methyltransferase with UbiX in Escherichia coli Coenzyme Q Biosynthesis journal August 2006
Metabolic Analysis of Escherichia coli in the Presence and Absence of the Carboxylating Enzymes Phosphoenolpyruvate Carboxylase and Pyruvate Carboxylase journal May 2000
The inhibition by substrate analogues of γ-aminobutyrate aminotransferase from mitochondria of different subcellular fractions of rat brain journal April 1977
Purification and Characterization of Methylmalonate-semialdehyde Dehydrogenase from Rat Liver journal September 1989
The biological degradation of cellulose journal January 1994
Feasibility of acrylic acid production by fermentation journal February 2005
Overproduction of phage Lambda repressor under control of the lac promotor of Escherichia coli journal January 1976
FolM, A New Chromosomally Encoded Dihydrofolate Reductase in Escherichia coli journal November 2003
Extensive mosaic structure revealed by the complete genome sequence of uropathogenic Escherichia coli journal December 2002
Bioengineering for Microbial Inulinases: Trends and Applications journal July 2017
The IdhA Gene Encoding the Fermentative Lactate Dehydrogenase of Escherichia Coli journal January 1997
SCALEs: multiscale analysis of library enrichment journal November 2006
Characterization of Mutations Contributing to Sulfathiazole Resistance in Escherichia coli journal January 1998
Effect of poxB gene knockout on metabolism in Escherichia coli based on growth characteristics and enzyme activities journal September 2006
Malonyl-Coenzyme A Reductase in the Modified 3-Hydroxypropionate Cycle for Autotrophic Carbon Fixation in Archaeal Metallosphaera and Sulfolobus spp. journal October 2006
Biosynthetic pathways for 3-hydroxypropionic acid production journal February 2009
Genome sequence of Bacillus cereus and comparative analysis with Bacillus anthracis journal May 2003
A Single Mutation Converts a Novel Phosphotyrosine Binding Domain into a Dual-specificity Phosphatase journal November 1995
Acetate Metabolism in a pta Mutant ofEscherichia coli W3110: Importance of Maintaining Acetyl Coenzyme A Flux for Growth and Survival journal November 1999
Dihydrolipoamide Dehydrogenase Mutation Alters the NADH Sensitivity of Pyruvate Dehydrogenase Complex of Escherichia coli K-12 journal March 2008
Fe2(SO4)3·4H2O/concentrated H2SO4: an efficient catalyst for esterification journal March 2004
Feedback Inhibition of Chorismate Mutase/Prephenate Dehydrogenase (TyrA) of Escherichia coli: Generation and Characterization of Tyrosine-Insensitive Mutants journal November 2005
The commercial production of chemicals using pathway engineering journal December 2000
Characterization of two temperature-inducible promoters newly isolated from B. subtilis journal July 2007
A new preparation of trifluoromethanesulfinate salts journal July 2007
The overexpression and complete amino acid sequence of Escherichia coli 3-dehydroquinase journal September 1986
Engineering primary metabolic pathways of industrial micro-organisms journal March 2007
Naturally Occurring Adenines within mRNA Coding Sequences Affect Ribosome Binding and Expression in Escherichia coli journal November 2006
Genome-wide screening for trait conferring genes using DNA microarrays journal May 2002
Identification of a 21 amino acid peptide conferring 3-hydroxypropionic acid stress-tolerance to Escherichia coli journal January 2012
Regulation of fatty acid biosynthesis in Escherichia coli. journal January 1993
CHEMISTRY: Sugary Recipe Boosts Grow-Your-Own Plastics journal June 2006
The catabolite repressor/activator (Cra) protein of enteric bacteria. journal June 1996