Abstract is: In organic chemistry, keto acids or ketoacids (also called oxo acids or oxoacids) are organic compounds that contain a carboxylic acid group (−COOH) and a ketone group (>C=O). In several cases, the keto group is hydrated. The alpha-keto acids are especially important in biology as they are involved in the Krebs citric acid cycle and in glycolysis. Common types of keto acids include: * Alpha-keto acids, alpha-ketoacids, or 2-oxoacids have the keto group adjacent to the carboxylic acid. They often arise by oxidative deamination of amino acids, and reciprocally, they are precursors to the same. Alpha-keto acids possesses extensive chemistry as acylation agents. Furthermore, alpha-keto acids such as phenylpyruvic acid are endogenous sources for carbon monoxide (as a gasotransmitter) and pharmaceutical prodrug scaffold. Important representatives: * pyruvic acid, pervasive intermediate in metabolism. * oxaloacetic acid, a component of the Krebs cycle. * alpha-ketoglutarate, a 5-carbon ketoacid derived from glutamic acid. Alpha-ketoglutarate participates in cell signaling by functioning as a coenzyme. It is commonly used in transamination reactions. * Beta-keto acids, beta-ketoacids, or 3-oxoacids, such as acetoacetic acid, have the ketone group at the second carbon from the carboxylic acid. They generally form by the Claisen condensation. The presence of the keto group at the beta position allows them to easily undergo thermal decarboxylation. * Gamma-keto acids, Gamma-ketoacids, or 4-oxoacids have the ketone group at the third carbon from the carboxylic acid. Levulinic acid is an example. Keto acids appear in a wide variety of anabolic pathways in metabolism. For instance, in plants (specifically, in hemlock, pitcher plants, and fool's parsley), 5-oxo-octanoic acid is converted in enzymatic and non-enzymatic steps into the cyclic class of coniine alkaloids. When ingested sugars and carbohydrate levels are low, stored fats and proteins are the primary source of energy production. Glucogenic amino acids from proteins are converted to glucose. Ketogenic amino acids can be deaminated to produce alpha keto acids and ketone bodies. Alpha keto acids are used primarily as energy for liver cells and in fatty acid synthesis, also in the liver.
structural class of chemical entities | Q47154513 |
carboxylic acid | Q134856 |
ketone | Q170744 |
P268 | Bibliothèque nationale de France ID | 11983743f |
P508 | BNCF Thesaurus ID | 17624 |
P1417 | Encyclopædia Britannica Online ID | science/keto-acid |
P646 | Freebase ID | /m/026t_9j |
P227 | GND ID | 4044245-7 |
P11514 | Great Russian Encyclopedia portal ID | ketokisloty-688720 |
P3827 | JSTOR topic ID (archived) | keto-acids |
P244 | Library of Congress authority ID | sh85072096 |
P486 | MeSH descriptor ID | D007651 |
P672 | MeSH tree code | D02.241.755 |
P2004 | NALT ID | 2369 |
P8189 | National Library of Israel J9U ID | 987007543582205171 |
P349 | NDL Authority ID | 00575992 |
P2892 | UMLS CUI | C0022618 |
P910 | topic's main category | Category:Keto acids | Q8573024 |
Q24646431 | 2-KETOGLUCONATE FERMENTATION BY STREPTOCOCCUS FAECALIS |
Q72131972 | 2-Oxobutyric acid: Effects of its condensation products on lactate dehydrogenase activity |
Q72586385 | A C26-keto-acid from the oil of Cuspidaria |
Q76915781 | A KETOIC ACID FROM THE SEEDS OF PAPAVER SOMNIFERUM L |
Q76613693 | A SIMPLE METHOD OF DIFFERENTIATING BETWEEN SERUM LACTATE DEHYDROGENASE OF CARDIAC ORIGIN AND THAT DERIVED FROM OTHER TISSUES |
Q34244255 | A study of acetyl-CoA condensation with α-keto acids |
Q82134147 | A study of beta-hydroxy-alpha-keto acids |
Q78347964 | ABNORMAL BIOCHEMICAL BEHAVIOUR OF FIVE NORMAL HUMAN CERVIX TISSUES CULTIVATED IN VITRO IN SYNTHETIC MEDIUM |
Q34258127 | ACETYLORNITHINE DELTA-TRANSAMINASE. PARTIAL PURIFICATION AND REPRESSION BEHAVIOR |
Q53814597 | AMINO ACID SYNTHESIS IN CANCERATED CONNECTIVE TISSUES INDUCED BY THE EFFECT OF PLASTIC IMPLANTS |
Q51279808 | AN ALPHA-HYDROXY ACID DECARBOXYLASE IN BRAIN MICROSOMES |
Q72611037 | Amino acid and α-keto acid concentrations in plasma and blood of the liverless dog |
Q40254854 | BIOCHEMICAL CHANGES OCCURRING DURING SPORULATION OF BACILLUS CEREUS T. II. EFFECT OF ESTERS OF ORGANIC ACIDS ON SPORULATION |
Q76707089 | CITRIC ACID AS THE PRINCIPAL SERUM INHIBITOR OF CERULOPLASMIN |
Q76510185 | CLINICAL AND EXPERIMENTAL STUDIES ON ALPHA-KETO ACIDS METABOLISM. 3. FLUCTUATION OF THE EXCRETION OF ALPHA-KETO ACIDS IN THE URINE OF PANTOTHENIC ACID DEFICIENT RATS TO WHICH FRUCTOSE SODIUM GLUTAMATE AND ASPARTIC ACID ARE ADMINISTERED |
Q76726581 | CLINICAL, BIOCHEMICAL, AND NEUROPATHOLOGIC ASPECTS OF MAPLE SYRUP URINE DISEASE. A KETOACIDURIA OF THE OPEN CHAIN AMINOACIDS LEUCINE, ISOLEUCINE AND VALINE |
Q51270930 | COMPARISON OF THE ACTIONS OF HUMAN BRAIN, LIVER, AND HEART LACTIC DEHYDROGENASE VARIANTS ON NUCLEOTIDE ANALOGUES AND ON SUBSTRATE ANALOGUES IN THE ABSENCE AND IN THE PRESENCE OF OXALATE AND OXAMATE |
Q76959742 | CONDITIONS OF FORMATION OF IDONATE-GLUCONATE |
Q76915221 | CONGENTIAL TYROSINOSIS |
Q76805334 | CONTRIBUTION TO THE METABOLISM OF ALPHA-KETO ACIDS IN GLYCOGENOSIS WITH GLUCOSE-6-PHOSPHATASE INSUFFICIENCY |
Q34257016 | CONTROL OF ASPARTATE BETA-DECARBOXYLASE ACTIVITY BY TRANSAMINATION |
Q51256181 | CONTROL OF GLUTAMATE METABOLISM. THE EFFECT OF PYRUVATE |
Q53706606 | Carcinogenicity in mice of some fatty acid methyl esters. 1. Skin application |
Q72405942 | Chemistry of Amino Acids. VII. The Synthesis and Spectral Studies of Some 2-Piperidones bearing β-Keto Ester Groups |
Q72295454 | Chromatographic identification of carbonyl compounds VII. Thin-Layer chromatographic resolution of mixtures of keto acid methyl ester 2,4-dinitrophenylhydrazones |
Q71433732 | Circular dichroism of some steroidal α-ketols and their acetates |
Q71989248 | Concerning the keto acid analogues of essential amino acids |
Q34262268 | Condensation of arabinose 5-phosphate and phosphorylenol pyruvate by 2-keto-3-deoxy-8-phosphooctonic acid synthetase |
Q76850439 | DEGRADATION OF CATECHOL BY BACTERIAL ENZYMES |
Q51251937 | DETERMINATION OF ACETYLCOENZYME A IN BRAIN |
Q76823993 | EFFECT OF A THIAZOLIDINIC DERIVATIVE OF PYRIDOXAL PHOPHATE ON THE RESPIRATION OF VARIOUS TISSUES |
Q76508295 | EFFECT OF TATD AND TPD ON ALPHA-KETO ACIDS DURING GLUCOCORTICOID ADMINISTRATION |
Q78263328 | EFFECT OF TRANSAMINATION INHIBITORS ON VALINE BIOSYNTHESIS AND ITS KETO ANALOG IN PLANTS |
Q76512554 | ENZYMATIC DETERMINATION OF BLOOD L-MALIC ACID |
Q78328232 | ENZYMIC PROPERTIES OF MALATE DEHYDROGENASE OF BACILLUS SUBTILIS |
Q76556379 | EXPERIMENTS ON THE PAPER CHROMATOGRAPHIC DETECTION OF ALPHA-KETOCARBOXYLIC ACIDS IN THE FORM OF SOME CHEMICALLY IMPORTANT ACIDS |
Q82197111 | Effect of low-protein diet on deamination, reamination, and amino acid synthesis in the liver and kidney |
Q82196983 | Effect of low-protein diet on metabolism of amino acids and keto acids and on content of glycogen in the liver and muscles in white rats |
Q71225811 | Enzymic, ATP-Dependent cleavage of beta-methyl-delta-keto-delta(alpha beta)-hexenoic acid. I. Beta-methyl-delta-keto-delta(alpha beta)-hexenoic acid as acetyl donor |
Q40434491 | FORMATION OF VALINE BY STREPTOMYCIN-DEPENDENT ESCHERICHIA COLI |
Q78240868 | FREE KETO ACIDS IN AZOTOBACTER VINELANDII |
Q76465643 | Familial glyco-amino-ketoaciduric syndrome (clinical and physiopathological observations) |
Q58952392 | Formation of Ammonia from Glutamate by Mitochondria |
Q72175589 | Formation of an ascorbigen-like product from p-hydroxybenzyl alcohol and L-ascorbic acid |
Q72455477 | Further Studies on Ethylene Formation from α-Keto-γmethylthiobutyric Acid or β-Methylthiopropionaldehyde by Peroxidase in the Presence of Sulfite and Oxygen |
Q51279811 | GAMMA-HYDROXYBUTYRATE IN MAMMALIAN BRAIN. REVERSIBLE OXIDATION BY LACTIC DEHYDROGENASE |
Q42116480 | GENETIC BLOCKS IN THE ISOLEUCINE-VALINE PATHWAY OF NEUROSPORA CRASSA |
Q78405503 | GLYCOLYTIC CONTROL MECHANISMS. I. INHIBITION OF GLYCOLYSIS BY ACETATE AND PYRUVATE IN THE ISOLATED, PERFUSED RAT HEART |
Q76930041 | GRAVE KETOACIDOSIS AND DIABETIC COMA: ITS THERAPY |
Q67349729 | Gas chromatography of α-keto acids as their o-trimethylsilylquinoxalinol derivatives |
Q76650026 | HETEROZYGOTE TEST FOR MAPLE SYRUP URINE DISEASE. DETERMINATION OF THE ENZYMATIC ACTIVITY OF ALPHA-KETOISOCAPROIC ACID OXIDASE IN LEUKOCYTES |
Q76851903 | HIGH MOLECULAR DERIVATIVES OF VITAMIN A |
Q76512167 | HISTO-ENZYMOLOGICAL STUDY OF THE ISLANDS OF LANGERHANS OF THE RAT. EFFECT OF CORTISONE TREATMENT |
Q54188464 | III. SHORT-TERM AND LONG-TERM EFFECTS. A. SOME ASPECTS OF BASIC RADIATION BIOCHEMISTRY |
Q76814874 | IMPORTANCE AND REACTIVE CAPACITY OF ALPHA-KETO ACIDS |
Q76784560 | IMPROVED METHOD FOR DETERMINING ASCORBIC, DEHYDROASCORBIC AND DIKETOGULONIC ACIDS BY THE A. N. KLIMOV METHOD |
Q28320933 | Identification of cysteine as the reactive group in pyruvate kinase alkylated by 5-chloro-4-oxopentanoic acid |
Q58953015 | In vivo Peroxidase Inhibitor in Bush Bean (Phaseolus vulgaris)Leaves |
Q26800036 | Integrase Inhibitor Prodrugs: Approaches to Enhancing the Anti-HIV Activity of β-Diketo Acids |
Q66929891 | Investigations on beta ketosters (author's transl) |
Q78523702 | KETO ACID CONTENT OF CANDIDA TROPICALIS |
Q76786795 | KETO ACID FORMATION IN SUBMERGED CULTURES OF ACTINOMYCES VIOLACEUS 719 |
Q76940363 | KETO ACID PRODUCTION IN PSEUDOMONAS GROUP BACTERIAL CULTURES |
Q78551722 | KETO AND HYDROXYACIDS OF THE CYCLOPARAFFIN SERIES WITH CHOLERETIC ACTIVITY |
Q52508184 | Keto acids in the haemolymph ofDysdercus koenigii (Fabr.) |
Q72686019 | Keto acids of Mycobacterium azot-absorptum sp. n |
Q69161093 | Kinetic studies of acetyl coenzyme A activated phosphoenolpyruvate carboxylase; reverse effects with a fatty acid |
Q78561490 | LEUCINOSIS: A VARIANT OF BRANCHED-CHAIN KETO-ACIDURIA |
Q72763076 | Late-onset branched-chain ketoaciduria: (maple syrup urine disease) |
Q71511681 | Long-chain ethylene compounds. IV. Conjugated diketooctadecanoic acids |
Q78290708 | MALATE-VITAMIN K REDUCTASE, A PHOSPHOLIPID-REQUIRING ENZYME |
Q37413420 | METABOLIC ACTIVITY IN COXIELLA BURNETII |
Q40247792 | METABOLISM OF DICARBOXYLIC ACIDS IN ACETOBACTER XYLINUM |
Q76851503 | METABOLISM OF METHYLMALONYL‐CoA AND THE ROLE OF BIOTIN AND B12 COENZYMES* |
Q59086194 | Mechanism of β-Ketoadipate Formation by Bacteria |
Q54139928 | Metabolism of Bovine Semen. XVIII. Effect of Keto Acids on Glutamate Metabolism |
Q76680935 | NATURE OF THE FATTY ACIDS IN FATS FROM THE BOVINE BCG STRAIN OF MYCOBACTERIUM TUBERCULOSIS |
Q71885516 | Non-enzymatic transamination of histidine with ?-keto acids |
Q76795422 | ON THE BLOOD CONCENTRATION OF PYRUVIC ACID AND ALPHA-KETOGLUTARIC ACID IN PATIENTS WITH LIVER DISEASES. (CHANGES AFTER INTRAVENOUS ADMINISTRATION OF GLYCINE) |
Q50765952 | ON THE EFFECTS OF ADRENALINE LOAD ON ARTERIOVENOUS BLOOD ALCOHOL, PYRUVATES AND SUGAR IN DIABETIC SUBJECTS |
Q42965539 | ORGAN SPECIFICITY AND LACTATE-DEHYDROGENASE ACTIVITY. DIFFERENTIAL INHIBITION BY UREA AND RELATED COMPOUNDS |
Q78353608 | ORGANIC COMPOUNDS IN THE SPENT MEDIUM OF FERROBACILLUS FERROOXIDANS |
Q51281676 | OXIDATION OF L-AMINO ACIDS AND INCORPORATION INTO PROTEIN IN HOMOGENATES OF BRAIN AT TWO STAGES OF DEVELOPMENT |
Q44119763 | On the mechanism of sensitivity to leucine in the case of "leucine sensitive hypoglycemia". II. The hypoglycemic affect of alpha-ketobutyric acid in the case of "leucine sensitive hypoglycemia" |
Q78865005 | On the synthesis of amino acids from keto acids and ammonium salts in rat kidneys |
Q46771622 | On the vitamin C activity of 2-keto-L-gulonic acid in the guinea pig |
Q77125000 | PHYSIOLOGICAL-BIOCHEMICAL CHARACTERISTICS OF AROMA-PRODUCING STREPTOCOCCUS DIACETILACTIS CULTURES |
Q76851863 | PRECURSORS OF METHYL KETONES IN BUTTER |
Q77146310 | PREPARATION OF 5,7-O-ETHYLIDENE 2-KETO-3-DEOXY-HEPTONIC ACID (Ba SALT) |
Q42695859 | PREPARATION OF OPTICALLY ACTIVE GAMMA- AND DELTA-LACTONES BY MICROBIOLOGICAL REDUCTION OF THE CORRESPONDING KETO ACIDS |
Q77158587 | PROSTAGLANDINS AND RELATED FACTORS. 28. METABOLISM OF PROSTAGLANDIN E1 IN GUINEA PIG LUNG: THE STRUCTURES OF TWO METABOLITES |
Q30594749 | Proton magnetic resonance studies of alpha-keto acids |
Q70454061 | Pyruvate kinase substrate activity exhibited by homologs of phosphoenolpyruvate |
Q78384303 | REDUCTION OF AROMATIC KETO ACIDS BY RAT LIVER |
Q76620758 | RESEARCH ON THE AGING OF ENZYMES IN VITRO. IV. ON THE METHODOLOGY OF ENZYME DETERMINATION IN HUMAN ORGAN EXTRACTS AND SERUM |
Q76856913 | RESPONSE OF 1-ASPARTIC-4-CARBOXYLASE TO SELECTED INHIBITORS |
Q67432858 | Reaction of singlet oxygen with .alpha.-ketocarboxylic acids. Oxidative decarboxylation and peroxyacid formation |
Q70487321 | Reductive amination of branched chain keto acids by glutamate dehydrogenase from several animal sources |
Q69483344 | Reductive cleavage of phenylhydrazones of .alpha.-oxo acids to amino acids |
Q51283114 | SOME PROPERTIES OF RAT BRAIN MITOCHONDRIAL PREPARATIONS: RESPIRATORY CONTROL |
Q76707076 | STOICHIOMETRY AND LOCALIZATION OF ADENOSINE TRIPHOSPHATE-DEPENDENT SODIUM AND POTASSIUM TRANSPORT IN THE ERYTHROCYTE |
Q76857062 | STUDIES ON SPECIFIC ENZYME INHIBITORS. VI. CHARACTERIZATION AND MECHANISM OF ACTION OF THE ENZYME-INHIBITORY ISOMER OF MONOFLUOROCITRATE |
Q77164694 | STUDIES ON THE ADAPTATION TEMPERATURE ON THE RESISTANCE AND ACTIVITY OF TRANSAMINASES IN YEAST CELLS |
Q36400065 | STUDIES ON THE GRAM-NEGATIVE CELL WALL. I. EVIDENCE FOR THE ROLE OF 2-KETO- 3-DEOXYOCTONATE IN THE LIPOPOLYSACCHARIDE OF SALMONELLA TYPHIMURIUM |
Q33971951 | STUDIES ON THE METABOLISM OF THE BENZENE RING OF TRYPTOPHAN IN MAMMALIAN TISSUES. I. ENZYMIC FORMATION OF GLUTARIC ACID FROM 3-HYDROXYANTHRANILIC ACID |
Q42061944 | STUDIES ON THE MUCIN DERIVED FROM HUMAN COLLOID BREAST CARCINOMA |
Q77122369 | SYNTHESIS OF GAMMA-KETO-N-CAPROIC ESTER |
Q71210065 | Selective Inactivation of the Glutamine Binding Site of Escherichia coli Carbamyl Phosphate Synthetase by 2-Amino-4-oxo-5-chloropentanoic Acid* |
Q70627153 | Structure of the Dimeric α-Keto Acid Analogue of Asparagine |
Q72669290 | Synthesis of aminolevulinic-(5-C14) acid and 5-dioxovaleric-(5-C14) acid |
Q77139408 | THE BASIS FOR ELEVATION OF SERUM GLUTAMIC PYRUVIC TRANSAMINASE LEVELS IN SERUM STORED ON CLOTS |
Q76834995 | THE CITRATE CLEAVAGE ENZYME. III. CITRYL COENZYME A AS A SUBSTRATE AND THE STEREOSPECIFICITY OF THE ENZYME |
Q35447424 | THE COMPOSITION AND BIOSYNTHESIS OF MILK LIPIDS |
Q76542577 | THE EFFECT OF THIOCTIC ACID ON BLOOD ALPHA-KETO ACID LEVELS IN LIVER DISEASES |
Q42965883 | THE EFFECTS OF ADENINE NUCLEOTIDES ON PYRUVATE METABOLISM IN RAT LIVER |
Q51692630 | THE GLYOXYLIC ACID CONTENT OF HUMAN BLOOD AND ITS RELATIONSHIP TO THIAMINE DEFICIENCY |
Q51281683 | THE INHIBITION OF CEREBRAL DIGLYCINASE BY α‐AMINO‐, α‐KETO‐ AND α‐HYDROXY ACIDS* |
Q42137171 | THE REDUCTION OF 5-OXODECANOIC ACID BY NORMAL BAKER'S YEAST |
Q76850467 | THIN-LAYER CHROMATOGRAPHY OF CARBOXYLIC ACIDS AND KETO ACIDS OF BIOLOGICAL INTEREST |
Q51277469 | TRANSAMINATION OF AROMATIC AMINO ACIDS IN RAT BRAIN |
Q78335147 | TRANSAMINATION OF KETO ACIDS WITH GAMMA-AMINOBUTYRIC ACID AND ITS RELATION TO GLYOXYLIC ACID |
Q76998448 | TRYPTOPHAN-ALPHA-OXOGLUTARATE TRANSAMINASE IN MATURING RAT LIVER |
Q44457798 | The Influence of Steric and Electronic Parameters on the Substrate Behaviour of alpha-Oxo Acids to Yeast Pyruvate Decarboxylase |
Q72239464 | The formation of an enzyme-bound β-carbanion in the enzymic conversion of l-homoserine to α-ketobutyrate |
Q42918513 | The oxidation of Schiff bases of pyridoxamine with α-oxo acids by manganous ions and peroxidase |
Q42728588 | The preparation of α-oxo acid derivatives suitable for specific-radioactivity determination |
Q71736962 | The stereochemistry of pyruvate kinase |
Q76485450 | The synthesis of 2-acetoxy of 2-acetoxy-delta12:13-30-oxymethyl-keto-oleanenic acid and the others of glycyrrhetinic acid derivatives, the pharmacological studies of its derivatives and D. C. A |
Q66917364 | Thiamine increases the specific activity of human liver branched chain α-ketoacid dehydrogenase |
Q52107665 | Use of keto acids in inborn errors of urea synthesis |
Q76717557 | VARIOUS ASPECTS OF KETOACIDURIA AND KETOACIDEMIA IN DIABETICS: URINARY EXCRETION AND HEMATIC LEVELS OF ALPHA-KETOISOCAPROIC ACID, ALPHA-KETOISOVALERIC ACID, PYRUVIC ACID AND ALPHA-KETOGLUTARIC ACID |
Q78801232 | alpha-Keto acid dehydrogenation complexes. I. Purification and properties of pyruvate and alpha-ketoglutarate dehydrogenation complexes of Escherichia coli |
Q78801237 | alpha-Keto acid dehydrogenation complexes. II. The role of protein-bound lipoic acid and flavin adenine dinucleotide |
Q78801241 | alpha-Keto acid dehydrogenation complexes. III. Purification and properties of dihydrolipoic dehydrogenase of Escherichia coli |
Q76487689 | alpha-Keto acid dehydrogenation complexes. IV. Resolution and reconstitution of the Escherichia coli pyruvate dehydrogenation complex |
Q71165860 | α-Keto analogues of amino acids as inhibitors of α-chymotrypsin, carboxypeptidase A, and pepsin |
Q76852704 | oxaloacetates | facet of | P1269 |
Q497173 | oxoacid | different from | P1889 |
Q8573024 | Category:Keto acids | category's main topic | P301 |
Q17116068 | pseudoacid | tautomer of | P6185 |