Metabolism of amino acids. Vladimíra Kvasnicová

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1 Metabolism of amino acids Vladimíra Kvasnicová

2 Classification of proteinogenic AAs -metabolic point of view 1) biosynthesis in a human body nonessential (are synthesized) essential (must be present in a diet) 2) degradation within cells glucogenic (Glc can be formed from their carbon sceleton) ketogenic (= AAs degraded to acetyl-coa)

3 Essential amino acids 1) branched chain: Val, Leu, Ile 2) aromatic: Phe ( Tyr), Trp 3) basic: His, Arg, Lys 10 4) sulfur-containing: Met ( Cys) 5) other: Thr

4 Essential amino acids PVT TIM HALL 1) branched chain: Val, Leu, Ile 2) aromatic: Phe ( Tyr), Trp 3) basic: His, Arg, Lys 4) sulfur-containing: Met ( Cys) 5) other: Thr

5 Essential / conditionally essential / nonessential amino acids essential: Val, Leu, Ile, Thr, Phe, Trp, His, Arg, Lys, Met noness.: Gly, Ala, Pro, Ser, Tyr, Asn, Gln, Asp, Glu, Cys AAs ~ organically bound nitrogen dietary proteins proteosynthesis body proteins AAs pool N-compound synthes. de novo biosynthesis degradation (E,glc,fat)

6 Insertion of an inorganic nitrogen to organic comp. in a human metabolism The figure is from (Jan 2007)

7 Synthesis of AAs in a human body - 5 substrates - 1. oxaloacetate Asp, Asn 2. α-ketoglutarate Glu, Gln, Pro, (Arg) 3. pyruvate Ala 4. 3-phosphoglycerate Ser, Cys, Gly 5. Phe Tyr

8 Synthesis of AAs in a human body - important reactions - 1. transamination Pyr Ala OA Asp α-ketoglt Glu 2. amidation Asp Asn Glu Gln 3. synthesis from other amino acids Phe Tyr Ser Gly Glu Pro Met + Ser Cys

9 Transamination reaction! REVERSIBLE! enzymes: amino transferases coenzyme: pyridoxal phosphate (vit. B6 derivative) The figure is from (Jan 2007)

10 Amino transferases important in medicine ( transaminases ) alanine aminotransferase (ALT = GPT) aspartate aminotransferase (AST = GOT) The figure was adopted from Devlin, T. M. (editor): Textbook of Biochemistry with Clinical Correlations, 4th ed. Wiley-Liss, Inc., New York, ISBN

11 amidation of glutamate = side chain carboxylic group of Glu is converted to amide group glutamine synthetase GLUTAMINE = the most important transport form af amino nitrogen in blood The figure was adopted from Devlin, T. M. (editor): Textbook of Biochemistry with Clinical Correlations, 4th ed. Wiley-Liss, Inc., New York, ISBN

12 Synthesis of ASPARAGINE needs glutamine as NH 2 group donor (it is not ammonia as in the Gln synthesis) The figure was adopted from Devlin, T. M. (editor): Textbook of Biochemistry with Clinical Correlations, 4th ed. Wiley-Liss, Inc., New York, ISBN

13 Synthesis of Tyr from Phe The figure is from (Jan 2007)

14 glycolysis Synthesis of serine and glycine The figure is from (Jan 2007)

15 Formation of activated methionine = S-adenosylmethionine (SAM) SAM is used as CH 3 group donor in metabolic methylations The figure is from (Jan 2007)

16 Synthesis of Cys from Met and Ser The figure is from (Jan 2007)

17 The figure is from (Jan 2007)

18 B12 Regeneration of Met (vitamins: folate+b 12 ) The figure is from (Jan 2007)

19 Some amino acids are used for synthesis of other N-compound: 1) Gln, Asp, Gly purines, pyrimidines 2) Gly porphyrines, creatine (+ Arg and Met) 3) Arg NO 4) Cys taurine The figure was adopted from Devlin, T. M. (editor): Textbook of Biochemistry with Clinical Correlations, 4th ed. Wiley-Liss, Inc., New York, ISBN

20 Decarboxylation of AAs gives monoamines (= biogenic amines) 1) Tyr catecholamines (adrenaline, noradrenaline, dopamine) 2) Trp serotonin (= 5-hydroxytryptamine) 3) His histamine 4) Ser etanolamine choline acetylcholine 5) Cys cysteamine Asp β-alanine coenzyme A Glu γ-aminobutyrate (GABA)

21 TEST / Choose correct statement(s) a) valine is a branched chain amino acid b) serine contains thiol group in its side chain c) glutamate is an essential amino acid d) tryptophan is a precursor of catecholamines

22 Degradation of amino acids (AAs) 1) -NH 2 group removing from AA 2) detoxification of the amino group 3) metabolism of carbon sceleton of AA 7 products

23 7 degradation products of AAs 1. pyruvate Gly, Ala, Ser, Thr, Cys, Trp 2. oxaloacetate Asp, Asn 3. α-ketoglutarate Glu, Gln, Pro, Arg, His 4. succinyl-coa Val, Ile, Met, Thr 5. fumarate Phe, Tyr 6. acetyl-coa Ile glucogenic AAs ketogenic AAs 7. acetoacetyl-coa Lys, Leu, Phe, Tyr, Trp

24 The entrance of amino acids into the citrate cycle The figure is from (Jan 2007)

25 An example of AA degradation to produce intermediate of the citrate cycle The figure is from (Jan 2007)

26 Fate of amino nitrogen derived from AAs a) in extrahepatic tissues transamination (forms mainly Ala and Glu + 2-oxoacids) deamination (only some AAs: Ser,Thr,His; releases NH 3 ) amidation Glu + NH 3 Gln (needs ATP) b) in the liver see a) oxidative deamination of Glu (forms α-ketoglt + NH 3 ) enzyme: glutamate dehydrogenase (GMD = GLD)

27 Glutamine is principal transport form of amino nitrogen The figure is from (Dec 2006)

28 Transport of amino nitrogen from degraded muscle proteins excreted products The figure was adopted from Devlin, T. M. (editor): Textbook of Biochemistry with Clinical Correlations, 4th ed. Wiley-Liss, Inc., New York, ISBN

29 Glucose-alanine cycle The figure was adopted from Devlin, T. M. (editor): Textbook of Biochemistry with Clinical Correlations, 4th ed. Wiley-Liss, Inc., New York, ISBN

30 Metabolism of amino nitrogen The figure is from (Jan 2007)

31 GLUTAMATE DEHYDROGENASE removes amino group from carbon skeleton of Glu in the liver 1. NH 2 from AAs was transfered by transamination Glu 2. free ammonia is released by oxidative deamination of Glu The figure is from (Jan 2007)

32 Transport and detoxification of amino nitrogen - SUMMARY - aminotransferases glutamate or alanine glutamine synthetase glutamine glutaminase glutamate + NH 4 + glutamate dehydrogenase 2-oxoglutarate + NH 4 + liver: urea cycle urea kidneys: glutaminase glutamate + NH 4 + urine

33 TEST / The products can be formed from carbon skeleton of the amino acids: a) aspartate oxaloacetate b) lysine glucose c) alanine fat d) glutamine α-ketoglutarate

34 TEST / Amino nitrogen released from carbon skeletons of AAs can be transported in blood as a) NH + 4 b) alanine c) glutamine d) urea

35 Urea (ornithine) cycle = detoxification pathway (NH 3 is toxic for brain) proceeds only in the liver is localized in mitochondria /cytoplasm carbamoyl phosphate synthetase I (= mitoch.) can acidify the organism (consumes HCO 3- ) needs energy (3 ATP, but 4 energy rich bonds) is connected with citrate cycle through fumarate urea is end product of NH 2 metabolism ( urine)

36 Detoxification of ammonia in the liver The figure is from (Jan 2007)

37 Interconnection of the urea cycle with the citrate cycle The figure is from (Jan 2007)

38 Regulation of urea cycle allosteric regulation + enzyme induction by protein rich diet or by metabolic changes during starvation regulatory enzyme carbamoyl phosphate synthetase I (= mitochondrial) activation N-acetylglutamate inhibition N-acetylglutamate synthetase arginine Urea synthesis is inhibited by acidosis HCO 3- is saved

39 TEST / Detoxification of ammonia in a human body includes a) urea cycle proceeding only in the liver b) cleavage of glutamine in the liver and the kidneys c) consumption of energy in a form of ATP d) formation of ornithine from citrulline and carbamoyl phosphate

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