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Amino Acid MetabolismRole of Amino AcidsProtein Monomeric UnitsEnergy SourcePrecursors (Nitrogen-containing Compounds)Precursors (a-ketoacids)Classification (Mammals)Amino Acid Deamination (First Reaction in Amino Acid Breakdown)Aminotransferases (Transaminases)Oxidative DeaminationAmino Acid OxidaseTransamination (Reactions)Transamination (Enzyme Cofactor)Transamination(1) Transimination(2) TautomerizationResonance-stabilized IntermediateSlide 18(3) Hydrolysis(4) Transfer of AmineResonance StabilizationSlide 22SummaryDegradative Fates of Glutamate Regeneration of a-KetoglutarateGlutamate-Aspartate AminotransferaseGlutamate Dehydrogenase (Oxidative Deamination)Formation of UreaSlide 28Urea CycleUrea Cycle (Introduction)Nitrogen Waste ProductsClassification of Organisms (Nitrogen Excretion Patterns)Overall Urea Cycle (Liver)Glutamate Dehydrogenase (Generation of NH3)Carbamyl Phosphate Synthetase (CPS) (Mitochondrion)Carbamyl Phosphate Synthetase (CPS)Slide 37Activation of HCO3– by ATPDisplacement of Phosphate by NH3Phosphorylation of Carbamate by ATPOrnithine Transcarbamylase (OTC) (Mitochondrion)PowerPoint PresentationArgininosuccinate Synthetase (Cytosol)MechanismArgininosuccinase (Cytosol)Arginase (Cytosol)Ornithine TransportSlide 48Recovery of ATPGlutamate DehydrogenaseRegeneration of Aspartate (Cytosol)Oxidation of 2 NADH Yields 6 ATPRegulation of the Urea CycleActivatorFormation of N-acetylglutamateDeficiencies of the Urea CycleMetabolic Breakdown of Individual Amino AcidsProducts of Amino Acid BreakdownAnimals cannot carryout net synthesis of precursors of gluconeogenesis from acetyl-CoA or acetoacetateConversion of Pyruvate and Oxaloacetate to PEP (Gluconeogenesis)Degradation to PyruvateCysteineAlanineGlycine, Threonine and SerineAmino Acid MetabolismIntroductionRole of Amino Acids•Protein monomeric units•Energy source•Precursors of other biological moleculesProtein Monomeric Units+H3N CR1HCOO– +H3N CR2HCOO–H2O+H3N CR1HC NH C COO–R2OH+Energy SourceAmino AcidsWaste ProductsADP + Pi ATPPrecursors(Nitrogen-containing Compounds)•Heme•Nucleotides•Amines•Nucleotide Coenzymes•GlutathionePrecursors(-ketoacids)Amino AcidsPyruvateOxaloacetateα-Ket oglutarat eGlucoseFatty AcidsKetone BodiesClassification(Mammals)•Essential amino acids•Non-essential amino acidsAmino Acid Deamination(First Reaction in Amino Acid Breakdown)+H3N CRCOO–HR COCOO–OAAH2NCNH2Oα-keto acidGlutamat eAspartateFumarat eUreaaKGαKGNitrogen-containing compoundsUreaCycleAminotransf erases(Transaminases)Aminotransferases(Transaminases)Amino Acid + α-Ketoglut arateα-Ket o Acid + GlutamateGlutamate + Oxaloacet at eα-Ket oglutarate + AspartateOxidative DeaminationGlutamat e + NAD(P)+ + H2Oα-Ketoglutarat e + NH4+ + NAD(P)H + H+GlutamateDehydrogenaseAmino Acid OxidaseAmino Acid + FAD + H2O α-Keto Acid + NH3 + FADH2FADH2 + O2FAD + H2O2Transamination(Reactions)Amino Acid + Enzymeα -Keto Acid + Enzyme–NH2Enzyme–NH2 + α -KetoglutarateEnzyme + GlutamateTransamination(Enzyme Cofactor)N CH3HH2CCH OOHPyridoxal-5'-P(PLP)PON CH3HH2CH2COHHOOHPyridoxine(Vitamin B6)N CH3HH2CH2COHPONH2Pyridoxamine-5'-P(PMP)TransaminationEnzyme Mechanism(1) TransiminationN CH3HPCH NHO–(CH2)4Enzyme–B:R CαHNH2COO–+N CH3HPCH NHO–R CαHCOO–Enzyme–B:α -Amino AcidEnzyme-PLPSchiff BaseAmino Acid-PLP Schiff Base(aldimine)Lys(2) TautomerizationN CH3HPCH NHO–R CαHCOO–Enzyme–B:LysN CH3HPCH NHO–R CαCOO–Enzyme–BH+LysResonance-stabilized IntermediateN CH3HPCH NHO–R CαCOO–Enzyme–BH+LysN CH3HPCH NHO–R CαCOO–Enzyme–BH+LysResonance-stabilized IntermediateN CH3HPCH NHO–R CαCOO–Enzyme–BH+LysN CH3HPCH NHO–R CαCOO–Enzyme–B:LysHKetimine(3) HydrolysisN CH3HPCH NHO–R CαCOO–Enzyme–B:LysHN CH3HPCO–H HNHCαR COO–OHEnzyme–B:LysOH–N CH3HPCO–H HNH2R CαOCOO–Enzyme–B:LysPyridoxamine Phosphate(PMP) Enzymeα -Keto Acid(4) Transfer of AminePMP-Enzyme + α -ketoglutaratePLP-Enzyme + GlutamateResonance StabilizationN CH3HPCH NHO–R CαHCOO–Resonance Stabilization•Transaminaton•Decarboxylation•Removal of R groupSummaryAmino Acid + α -Ketoglutarateα -Keto Acid + GlutamateDegradative Fates of GlutamateRegeneration of -KetoglutarateOAANH4+H2NCNH2OCO2GlutamateAspartateFumarateUreaαKGNitrogen-containing compoundsUreaCycleα-ketoacidAmino Acidα-KGCarbon and EnergyGlutamate-Aspartate AminotransferaseGlutamate + Oxaloacetate α -Ketoglutarate + AspartateGlutamate Dehydrogenase(Oxidative Deamination)C COO–CH2H2C+H3NHCOO–GlutamateC COO–CH2H2CH2NCOO–NAD(P)+ NAD(P)H + H+C COO–CH2H2COCOO–H2O NH4+α -Ketoglutarateα -IminoglutarateFormation of UreaAspartate + HCO3- + NH4+UreaUrea CycleDegradative Fates of GlutamateRegeneration of -KetoglutarateOAANH4+H2NCNH2OCO2GlutamateAspartateFumarateUreaαKGNitrogen-containing compoundsUreaCycleα-ketoacidAmino Acidα-KGCarbon and EnergyUrea CycleUrea Cycle(Introduction)Catabolism(Oxidation)ADPATPNADP+NADPHIntermediatesAnabolism(Biosynthesis)ProteinsFatsCarbohydrates(Nutrients)Waste(CO2/Urea/etc.)Nitrogen Waste ProductsNH3H2NCNH2ONNNNOOHOAmmonia Urea(Vertebrates)Uric Acid(Birds and Reptiles)Require less water for excretionClassification of Organisms(Nitrogen Excretion Patterns)•Ammonotelic: ammonia excreting•Ureotelic: urea excreting•Uricotelic: uric acid excretingOverall Urea Cycle(Liver)NH3 + HCO3– +H2NCNH2OH3N C COO–H2CHCOO–3ATP 2ADP + 2Pi + AMP + PPi+HC COO–CH–OOCAspartateUrea Fumarate+Glutamate Dehydrogenase(Generation of NH3)Glutamate + NAD(P)+ + H2Oα -Ketoglutarate + NH3 + NAD(P)H + H+Carbamyl Phosphate Synthetase (CPS)(Mitochondrion)H2N COOPCarbamyl Phosphate2ATP 2ADP + PiNH3 + HCO3–Carbamyl Phosphate Synthetase (CPS)•CPSI (Mitochondria)–Uses NH3–Urea Cycle•CPSII (Cytosol)–Uses Glutamine–Pyrimidine BiosynthesisCarbamyl Phosphate Synthetase (CPS)MechanismActivation of HCO3– by ATPHO COO–Bicarbonate(CO2)+–O POO–O ADPADPHO COO PCarbonyl-PDisplacement of Phosphate by NH3HO COO P + NH3PiH2N COO–CarbamateCarbonyl-PPhosphorylation of Carbamate by ATPH2N COO–ATP ADPH2N COOPCarbamyl PhosphateCarbamateOrnithine Transcarbamylase (OTC)(Mitochondrion)H2N COO P++H3N C COO–H(CH2)3NH3+OrnithinePi+H3N C COO–H(CH2)3NHCO NH2CitrullineCarbamoyl PNon-standard amino acids(not present in proteins)Citrulline Carrier(Ornithine Antiport)Argininosuccinate Synthetase(Cytosol)+H3N C COO–H(CH2)3NHCO NH2Citrulline+ C+H3N COO–HH2C COO–AspartateATP


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UCLA CHEM 153C - (6)_AA_Metabolism_I

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