Protein and amino acidProtein and amino acidmetabolismmetabolism

SIBCSIBC511511ChayanonChayanon PeerapittayamongkolPeerapittayamongkol,,

JulyJuly 66thth,, 2007

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TopicsTopics

Digestion and absorption of proteinsDigestion and absorption of proteinsIntracellular degradation of proteinsIntracellular degradation of proteinsNitrogen metabolismNitrogen metabolism

Nitrogen balanceNitrogen balanceAmino acid degradationAmino acid degradationUrea cycleUrea cycleMetabolism of the carbon skeletons of amino acidsMetabolism of the carbon skeletons of amino acidsInherited diseases of amino acid metabolismInherited diseases of amino acid metabolismAmino acid biosynthesisAmino acid biosynthesisConversions ofConversions of aaaa to other biological aminesto other biological amines

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ubiquitin,proteasome

in cells

Digestion

(intestine)

in liver

via kidney

connection

catabolism

anabolism

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“N-end rule”

Protein turnover (intracellular)Protein turnover (intracellular)Clic

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ProteasomeProteasome digestsdigeststhethe ubiquitinubiquitin--tagged proteinstagged proteins

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UbiquitinUbiquitin ((88..55 kDkD))Present in allPresent in alleukaryoteseukaryotesHighly conservedHighly conservedFormForm isopeptideisopeptidebond with targetbond with targetproteinsproteins

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UbiquitinUbiquitin conjugationconjugation

E1: ubiquitinactivating enzyme

E2: ubiquitin conjugatingenzyme

E3: ubiquitin-protein ligase

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2626SS proteasomeproteasome

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ApplicationsApplications

EE33, the reader of N, the reader of N--terminal residuesterminal residuesCyclinCyclin destruction in cell cycledestruction in cell cycleProteins rich in PEST sequenceProteins rich in PEST sequenceHPV encodes protein that activates EHPV encodes protein that activates E33

then Ethen E33 ubiquitinatesubiquitinates pp5353 (tumor(tumorsuppresorsuppresor)) degradeddegraded cervical CAcervical CA

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DigestionDigestion

acidacid denaturationdenaturationpepsin,pepsin,

primaryprimary proteolyticproteolyticenzymeenzyme

pancreaticpancreaticenzymesenzymes

trypsintrypsinchymotrypsinchymotrypsinelastaseelastase

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AbsorptionAbsorption

oligpeptidesoligpeptides==didi--,, tripeptidestripeptides----absorbableabsorbable

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ubiquitin,proteasomein cells

Digestion(intestine)

in liver

via kidney

connection

catabolism

anabolism

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Nitrogen balanceNitrogen balance

A wellA well--nourished adult is said to be in nitrogen equilibrium ornourished adult is said to be in nitrogen equilibrium ornormal nitrogen balance ifnormal nitrogen balance if

Dietary intake of nitrogen = Nitrogen loss (throughDietary intake of nitrogen = Nitrogen loss (throughexcretion and other processes, such as perspiration)excretion and other processes, such as perspiration)

Positive nitrogen balance occurs when:Positive nitrogen balance occurs when:

Dietary intake of nitrogen > Nitrogen lossDietary intake of nitrogen > Nitrogen loss

Negative nitrogen balance occurs when:Negative nitrogen balance occurs when:

Dietary intake of nitrogen < Nitrogen lossDietary intake of nitrogen < Nitrogen loss

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Nitrogen balance (application)Nitrogen balance (application)

Daily protein recommendation:Daily protein recommendation: 00..88g/kg/dayg/kg/day11..44--11..77 g/kg/day for strength athletesg/kg/day for strength athletes totomaintain muscle massmaintain muscle massBalance between the rate of proteinBalance between the rate of proteinsynthesis and protein breakdownsynthesis and protein breakdownExcess intake >Excess intake > 33 g/kg/dayg/kg/day have negativehave negativeeffecteffect

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Amine group removal (Amine group removal (deaminationdeamination))

11.Transamination :.Transamination : transaminasetransaminase22.Oxidative.Oxidative deaminationdeamination :: glutamateglutamate

dehydrogenasedehydrogenase, L, L--amino acidamino acid oxidaseoxidase33.Dehydratase : removal of water first and.Dehydratase : removal of water first and

then followed bythen followed by deaminationdeamination e.ge.g serineserinedehydratasedehydratase andand threoninethreonine dehydratasedehydratase

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--Amino acids andAmino acids and --ketoketo acidsacids

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TransaminationTransamination

EnzEnz:: transaminasetransaminase,, aminotransferaseaminotransferaseMecMec: transfer of: transfer of --amino group fromamino group from --amino acid to anamino acid to an --ketoacidketoacid——usuusu.. --ketolgutarateketolgutarateAspartateAspartate aminotransferaseaminotransferase::aspartateaspartate ++ --ketoglutarateketoglutarate oxaloacetateoxaloacetate + glutamate+ glutamate

AlanineAlanine aminoamino transferasetransferase::alaninealanine ++ --ketoglutarateketoglutarate pyruvatepyruvate + glutamate+ glutamate

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PingPing--pong reactionpong reaction

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TransaminationTransamination

--ketoglutateketoglutate oftenoftenused by manyused by manytransaminasetransaminaseallall transaminasestransaminasescontaincontain pyridoxalpyridoxalphosphatephosphate(prosthetic(prosthetic grgr))Occur in mostOccur in mosttissuestissues

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Aspartate aminotransferase

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Vitamin BVitamin B66

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TransaminationTransamination followed by oxidativefollowed by oxidativedeaminationdeamination

aminotransferase glutamate dehydrogenase

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Glutamate DHGlutamate DH

Release freeRelease freeammoniumammoniumOccur inOccur inmitochondrionmitochondrionAllosteric inhibitors

GTP, ATP

Allsteric activators

GDP, ADP

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Glucose-alanine cycle

Cori cycle

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Nitrogen transport to liverNitrogen transport to liver

Amino acid degradation occurs in tissues otherAmino acid degradation occurs in tissues otherthan liverthan liverMuscle usesMuscle uses aaaa during prolong exercise and fastingduring prolong exercise and fastingOnly liver contains all enzymes for urea cycleOnly liver contains all enzymes for urea cycleMuscle transports nitrogen in the form ofMuscle transports nitrogen in the form of alaninealanine(via glucose(via glucose ––alaninealanine cycle)cycle)Others transport nitrogen as glutamine viaOthers transport nitrogen as glutamine viaglutamineglutamine synthetasesynthetase

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GlutamineGlutamine

Formation of glutamineFormation of glutaminefrom glutamate, ATP,from glutamate, ATP,ammoniumammoniumOccurred in tissues otherOccurred in tissues otherthan liverthan liverGlutamine carriesGlutamine carriesnitrogen to livernitrogen to liver

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Action ofAction of glutaminaseglutaminase

Glutaminasealso presentin kidney butfor acid-baseregulation

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Urea cycleUrea cycle

11=carbamoyl phosphate synthetase=carbamoyl phosphate synthetase II::22==ornithine transcarbamoylaseornithine transcarbamoylase: ornithine is: ornithine is

carbamoylated citrullinecarbamoylated citrulline33==argininosuccinate synthetaseargininosuccinate synthetase: condensation of: condensation of

citrulline and aspartatecitrulline and aspartate44==argininosuccinaseargininosuccinase: cleavage of argininosuccinate: cleavage of argininosuccinate

into arginine and fumarateinto arginine and fumarate55==arginasearginase: arginine is hydrolyzed to urea and: arginine is hydrolyzed to urea and

ornithineornithine

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Regulation of urea cycle

CPSI needs N-acetylglutamate as an allostricactivator

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Urea cycle and citric acid cycleUrea cycle and citric acid cycle

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Fates ofFates of oxaloacetateoxaloacetate

FumarateFumarate oxaloacetateoxaloacetate = the link= the linkTransaminationTransamination toto aspartateaspartateConversion into glucose viaConversion into glucose via gluconeogenicgluconeogenicpathwaypathwayCondensation withCondensation with acetylCoAacetylCoA to form citrateto form citrateConversion intoConversion into pyruvatepyruvate

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AmmoniaAmmonia

Ammonia is toxicAmmonia is toxicBrain swelling (increase in the brain’s waterBrain swelling (increase in the brain’s watercontent)content)Increase in intracranial pressureIncrease in intracranial pressurePotential depletion of ATPPotential depletion of ATP

ammoniaammonia(( --ketoglutarateketoglutarate glutamateglutamate )) glutamineglutamine

osmolyteosmolyte in brainin brain astrocyteastrocyte

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Treatment of urea cycle defectTreatment of urea cycle defect

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Treatment of urea cycle defectTreatment of urea cycle defect

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CatabolismCatabolismClick t

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CatabolismCatabolism

Accounted forAccounted for 1010--1515% of human energy% of human energyproductionproduction2020 pathways converge topathways converge to 66 major productsmajor products

77 aaaa are broken down to acetylare broken down to acetyl--CoACoA55 aaaa toto --ketoglutarateketoglutarate44 toto succinylsuccinyl--CoACoA22 toto fumaratefumarate22 toto oxaloacetateoxaloacetate

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CatabolismCatabolism

PhePhe, Tyr, Ile,, Tyr, Ile, LeuLeu,, TrpTrp,, ThrThr, Lys, Lys acetoacetylacetoacetylCoACoA/or acetyl/or acetyl CoACoA ketoneketone bodies in liverbodies in liver((acetoacetateacetoacetate acetoneacetone --hydroxybutyratehydroxybutyrate) =) =ketogenicketogenicGlucogenicGlucogenic aaaa == pyruvatepyruvate,, --ketoglutarateketoglutarate,,succinylsuccinyl CoACoA,, fumaratefumarate and/orand/or oxaloacetateoxaloacetateTrpTrp,, PhePhe, Tyr,, Tyr, ThrThr, Ile both, Ile both ketogenicketogenic andandglucogenicglucogenic

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Enzyme cofactors in oneEnzyme cofactors in one--carboncarbontransfer reactiontransfer reaction

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Metabolism of methionineMetabolism of methionine

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Associated withatherosclerosisand neural tubedefect

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Six amino acids topyruvate

Most important pathwayfor glycine breakdown

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High levels in kidneyHigh levels in kidney7575% kidney stones% kidney stones——calcium oxalatecalcium oxalate

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Seven amino acids

to acetyl CoA

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human

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Phenylalanine

catabolism

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Phenylalanine hydroxylasePhenylalanine hydroxylase

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Minor pathwayMinor pathway

In PKUIn PKUphenylpyruvatephenylpyruvateaccumulate inaccumulate intissues, blood, urinetissues, blood, urineUrine also containsUrine also containsphenylacetate andphenylacetate andphenyllactatephenyllactate

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Five amino acids to -ketoglutarate

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Four amino acidsto succinyl CoA

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BranchedBranched--chain amino acidschain amino acids

in tissues otherthan liver

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Pathways of amino acid degradationPathways of amino acid degradation

Removal of their amino groupsRemoval of their amino groupsCarbon skeletons undergo oxidation toCarbon skeletons undergo oxidation tocommon intermediatescommon intermediatesSomeSome aaaa to glucose, some toto glucose, some to ketoneketone bodies,bodies,some to bothsome to bothAcetylAcetyl CoACoA,, --ketoglutarateketoglutarate,, succinylsuccinyl CoACoA,,fumaratefumarate andand oxaloacetateoxaloacetate

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Nitrogen cycleNitrogen cycle

The majority source of N is the air (NThe majority source of N is the air (N22))Nitrogen fixation: reduction of NNitrogen fixation: reduction of N22 to NHto NH44

++

By nitrogenBy nitrogen--fixing bacteria e.g.fixing bacteria e.g. RhizobiumRhizobium

Nitrification: oxidation of NHNitrification: oxidation of NH44++ to nitrite andto nitrite and

nitratenitrateBy soil bacteriaBy soil bacteria

DenitrificationDenitrification: conversion of nitrate to N: conversion of nitrate to N22under anaerobic conditionunder anaerobic condition

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NitrogenaseNitrogenase complexcomplex

Reduction of nitrogen to ammoniaReduction of nitrogen to ammonia

GG’’ ==--3333..55 kJ/molkJ/molActivation energyActivation energy

Bond energy =Bond energy = 930930 kJ/molkJ/molNitrogenaseNitrogenase complexcomplex

2 2 3N + 3H 2 NH

N N

+ - +2 4 i 2N +10H +8e +16ATP 2NH +16ADP+16P +H

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AmmoniaAmmonia GluGlu,, GlnGln

Assimilation of NHAssimilation of NH44++ into glutamateinto glutamate

requires two reactionsrequires two reactionsGlutamineGlutamine synthetasesynthetase

GlutamateGlutamate synthetasesynthetase

+ +4 iGlutamate+ NH + ATP glutamine+ ADP+ P + H

+ +- ketoglutarate+ glutamine+ NADPH+ H 2glutamate+ NADP

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GlutamineGlutaminesynthetase:synthetase:primaryprimaryregulatoryregulatoryinin E.coliE.coli

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Biosynthesis of amino acidsBiosynthesis of amino acids

NonessentialNonessentialamino acidsamino acids

Around half ofAround half of 2020aa can beaa can besynthesizedsynthesized

Essential aminoEssential aminoacidsacids

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Pro is aPro is a cyclizedcyclizedderivative ofderivative ofglutamateglutamateArgArg is synthesizedis synthesizedfrom glutamate viafrom glutamate viaornithineornithine and theand theurea cycleurea cycleOrnithineOrnithine isisinterconvertedinterconverted totoglutamateglutamate --semialdehydesemialdehyde bybyornithineornithine --aminotransferaseaminotransferase

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Major pathway forMajor pathway forsynthesis of serine issynthesis of serine isthe same in allthe same in allorganism.organism.First by oxidation ofFirst by oxidation ofhydroxyl group ofhydroxyl group of 33--phosphoglyceratephosphoglycerateTransaminattionTransaminattion fromfromgluglu yieldsyields 33--phosphoserinephosphoserine

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tryptophan

phenylalanine,tyrosine

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PRPP contributes five carbons, thePRPP contributes five carbons, the purinepurine ring of ATP contributesring of ATP contributesa nitrogen and a carbon, and glutamine supplies the seconda nitrogen and a carbon, and glutamine supplies the second

nitrogen atom.nitrogen atom.

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Synthesis of highSynthesis of highenergy compounds:energy compounds:Creatine phosphateCreatine phosphate

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GlycineGlycine as a precursor ofas a precursor of porphyrinsporphyrins

mammals

bacteria, plants

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Biosynthesis of hemeBiosynthesis of hemeClic

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Biological aminesBiological aminesfromfrom aaaa

decarboxylationdecarboxylation

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Biosynthesis of someneurotransmitters

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