Midterm 2. Low: 14 Mean: 61.3 High: 98. Standard Deviation: 17.7

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1 Midterm 2 Low: 14 Mean: 61.3 High: 98 Standard Deviation: 17.7

2 Lecture 17 Amino Acid Metabolism Review of Urea Cycle N and S assimilation Last cofactors: THF and SAM Synthesis of few amino acids

3 Dietary (Exogenous) Proteins Hydrolyzed in digestive system (~100 g/day) Replenish endogenous amino acids (muscle protein) Replenish glycogen stores (glucogenic amino acids) Excess intake to ATP production and lipid synthesis) Excess nitrogen is excreted (urea, ammonia) Nitrogen balance is typically zero

4 Endogenous Proteins A. Normal Protein Turnover ( g/day) Digestive enzymes (pancreas: >30 g/day) Plasma proteins Cell death (e.g., intestinal mucosa, immune system) Intracellular turnover (damaged proteins, enzyme regulation) B. Mobilization of Skeletal Muscle Protein Fasting, exercise, trauma, injury Gluconeogenesis Malnutrition (diets deficient in essential amino acids)

5

6 Amino Acids C-Skeletons NADH α-kga AA NADH Glu Dehydrogenase Asp Aminotransferase NAD + Glu NAD + NH + 4 Asp Malate Urea Cycle Fumarate H 2 N C NH 2 HC 3 - Review

7 Carbamoyl-P Synthetase NH 3 + HC ATP Carbamoyl amoyl-p + 2ADP + Pi Carbamoyl amoyl-p H 2 N-Asp rnithine Urea Cycle Fumarate Malate AA H 2 N C NHNH 2 Mitochondria and Cytosol Review

8 Skeletal Muscle Intracellular Proteolysis Amino Acids Amino Acid x Aminotransferases + α-kga α-keto Acid x + Glu Ala Aminotransferase Glu + Pyr α-kga + Ala To Liver

9 Skeletal Muscle Intracellular Proteolysis Amino Acids Amino Acid x Aminotransferases + α-kga α-keto Acid x + Glu Glu Dehydrogenase Glu + NAD + + H 2 α-kga + NADH + NH 3 Glutamine Synthetase NH 3 + Glu + ATP ADP + Pi + Gln To Liver To Kidneys

10 Liver Ala Aminotransferase Ala + α-kga Glu + Pyr Glucose Glutaminase NH 3 or Asp Gln + H 2 Glu + NH 3 Urea Kidneys Glutaminase Gln + H 2 Glu + NH 3 Urine

11 Muscles (other extrahepatic organs) B L D Ala Gln In conditions of metabolic acidosis Liver Urea Kidneys NH 3 HC - 3 Urea

12 The Cori and Alanine Cycle Glycogen Glucose Pyruvate Proteins Muscle Lactate Alanine Blood Liver Lactate Alanine Glycogen Glucose Pyruvate Urea p. 89

13 Degradation of Amino Acids: Fate of C-Skeletons Glucogenic Amino Acids: C-skeletons are converted to Pyruvate α-ketoglutarate Succinyl-CoA Fumarate xaloacetate (AA) Ketogenic Amino Acids: C-skeletons are converted to Acetyl-CoA Acetoacetate p. 90

14 Glucose Pyruvate Glucogenic Acetyl-CoA Ketogenic Lipids Ketone Bodies xalaoacetate Citrate Malate TCA Cycle Isocitrate Fumarate α-ketoglutarate Succinyl-CoA

15 Amino Acids Common Degradation Product nly glucogenic Ala, Cys, Gly, Ser, Thr Asp, Asn Met, Thr (humans), Val Arg, Glu, Gln, His, Pro Pyruvate AA Succinyl-CoA α-ketoglutarate nly ketogenic Leu, Lys Acetoacetate Ketogenic and glucogenic Phe, Tyr Trp Ile Fumarate, Acetoacetate Pyruvate, Acetyl-CoA Succinyl-CoA CoA, Acetyl-CoA p. 90

16 Nitrogen and Sulfur Assimilation (Amino Acid Synthesis)

17 Nitrogen and Sulfur Assimilation (Amino Acid Biosynthesis) LIGHT 2 ATP NADPH C 2 N 3-, N 2 S 2-4 Photosynthesis NADP + ADP + Pi H 2 Carbohydrates Amino Acids p. 91

18 Bioenergetics of Macronutrient Assimilation Electronegativity Assimilation (3.4) N (3.0) S (2.6) C (2.6) - N 3 2- S 4 C 2 NAD(P)H NAD(P)H + ATP NAD(P)H + ATP NH 3 H 2 S CH Photosynthesis H (2.2) H 2 (H 2 ) P (2.1) P 4 3- PH 3

19 Nitrate Assimiliation and Nitrogen Fixation A. Most Microorganisms, Fungi, and Plants Nitrate Reductase N NADH + H + N NAD + + H 2 Nitrite Reductase N Fd red + 8 H + NH H Fd ox B. Biological Nitrogen Fixation (Microorganisms) Nitrogenase N 2 + 8e H ATP + 16 H 2 2 NH ADP + 16 Pi + H 2 p. 91

20 Assimilation of Ammonia A. Major Pathway for Ammonia Net Assimilation (M, Fungi, Plants) Glutamine Synthetase (GS) NH 3 + Glu + ATP Gln + ADP + Pi Glutamate Synthase Gln + α-kga + NAD(P)H + H + 2 Glu + NAD(P) + Glutamate Aminotransferase (also present in animals) Glu + α-keto Acid α-kga + L-α-Amino Acid Glutamine Amidotransferase (also present in animals) Gln + R-H or R 1 -(C=)-R 2 Glu + R-NH 2 or R 1 -(C=NH)-R 2 p. 92

21 Assimilation of Ammonia B. Assimilation of Ammonia (no Net) via Carbamoyl-P P Synthesis (Urea Cycle) Carbamoyl-P synthetase I (Mitochondria) NH 3 + HC ATP Carbamoyl-P + 2 ADP + Pi p. 92

22 Assimilation of Ammonia A. Major Pathway for Ammonia Net Assimilation (M, Fungi, Plants) Glutamine Synthetase (GS) NH 3 + Glu + ATP Gln + ADP + Pi Glutamate Synthase Gln + α-kga + NAD(P)H + H + 2 Glu + NAD(P) + Glutamate Aminotransferase (also present in animals) Glu + α-keto Acid α-kga + L-α-Amino Acid Glutamine Amidotransferase (also present in animals) Gln + R-H or R 1 -(C=)-R 2 Glu + R-NH 2 or R 1 -(C=NH)-R 2 p. 92

23

24 Multi-level Regulation of Glutamine Synthetase (GS) Allosteric Regulation NH 3 + ATP ADP + Pi (-) Gly (-) Ala Glutamate Glutamine Synthetase (-) Glutamine AMP, CTP, His, Trp Carbamoyl-P Glucosamine-6-P p. 93

25 Covalent Modification and Allosteric Regulation (+) α-kga (+) ATP UT ( ) Gln Uridylylation UTP De-uridylylation AT P UMP De-adenylylation ATP Adenylylation Active GS AMP Inactive p. 93

26 The Nitogen Cycle p. 94

27 Sulfur Assimilation S 4 2- S P H H H H H H Adenosine monophosphate sulfate (APS) Adenine carrier AMP carrier-s-s 3-6 Reduced Ferredoxin 6 xidized Ferredoxin 2Fdox 2Fdred HS CH 2 CH C H carrier-s-s - NH 2 Cysteine Acetate H 3 C C CH 2 CH C H H NH 2 -acetyl serine p. 95

28 Sulfur Assimilation 2 Cysteine Acetate H 3 C C CH 2 CH C H H NH 2 -acetyl serine Pi CH 2 C C H 3-Phosphoglycerate (3PGA) H NAD + CoA NADH + H + Acetyl CoA Pi CH 2 C C H Glu Pi αkg CH 2 CH NH 2 C H H 2 Pi H CH 2 CH NH 2 C H Hydroxy-P-pyruvate -phospho-serine Serine p. 95

29 New Co-factor of Carbon Transfer Coenzyme A Acetyl- and acyl- groups TPP C2-aldehyde/keto groups Biotin Activated C 2 Tetrahydrofolic acid (THF) C1 groups of different oxidation states

30 Folic Acid and Tetrahydrofolic acid (THF) FLIC ACID H 2 N HN N N 8 5 N H CH 2 N H C - HN C CH CH2 CH 2 C - Pteridine ring (6-methyl pterin) p-amino benzoic acid Glutamate p. 96

31 Folic Acid NADPH + H+ NAD+ 7,8-Dihydrofolic Acid (DHF) Dihydrofolate reductase NADPH + H+ NADP+ H 2 N HN N H N H 6 9 NH H H CH 2 10 N H REST 5,6,7,8-Tetrahydrofolic Acid (THF) THF is a carrier of C1 units at different oxidation states p. 96

32 N 10 formyl THF N 5 N 10 methenyl THF N 5 N 10 methylene THF ATP ADP + Pi 6 9 NADPH + H + NADP + HC - HN 5 10 N CH H 2 N 5 10 C H N N 5 10 C H 2 N 6 9 HN 5 10 NH NADPH + H + Ser PLP H 2 NADP + Gly N 5 10 NH CH 2 H N 5 10 NH unstable CH 3 N 5 methyl THF p. 97

33 Tetrahydrofolate (THF) Carrier of C-1 units of different oxidation state N 10 -Formyl ( CH) N 5,N 10 -Methenyl ( CH=) N 5 -Methyl ( CH 3 ) N 5,N 10 -Methylene ( CH 2 ) C-1 units are derived from glycolysis 3-Phosphoglycerate Ser Ser Gly + N 5,N 10 -Methylene-THF + H 2 Gly NH 3 + C 2 + N 5,N 10 -Methylene-THF Met biosynthesis (N 5 -Methyl-THF; bacteria, fungi, plants) S-Adenosylmethionine (SAM) production Purine biosynthesis (N 10 -Formyl-THF)

34 A. Bacteria, Fungi, and Plants Synthesis of Sulfur-containing Amino Acids 3PGA THF N 5, N 10 Methylene THF Serine Glycine H + + NADH NAD + Acetyl-CoA THF N 5, N 10 Methylene THF N 5 Methyl THF THF CoA Cleavage Site S -Acetyl-serine S CH 2 S CH 2 CH 2 H C NH 3 H C NH 3 C SH C Cysteine Homoserine (-Phosphate) (-Acetyl) (-Succinyl) Cystathionine Succinate (or Acetate, or Pi) Homocysteine Methionine Vit. B 12 NH Pyruvate Aspartate AA p. 98

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