Dynamics of Protein And Amino Acid Metabolism
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2 Dynamics of Protein And Amino Acid Metabolism Dietary Proteins Digestion to Amino Acids Transport in Blood to Cells Protein Synthesis Functional Proteins Amino Acids Metabolites Protein Degradation In Proteasomes Following Tagging With Ubiquitin 2
3 Digestion of Proteins Stomach: Pepsinogen Pepsin (max. act. p 2) Small Intestine: Trypsinogen Enteropeptidase Trypsin Trypsin cleaves: Chymotrypsinogen to chymotrypsin Proelastase to elastase Procarboxypeptidase to carboxypeptidase Aminopeptidases (from intestinal epithelia) 3
4 Intestinal Absorption Amino Acids Oligopeptides Lumen Transport Protein Oligopeptides Peptidases Amino Acids Blood 4
5 Carbamoyl 1) 4 CO 3 2 ATP 2 Phosphate 2 CO 2 PO 3 2 ADP Carbamoyl Phosphate P i 2 Synthase I (CPSI) TCA Cycle mitochondria 2) 4 O O 2 CC 2 C 2 CCO 2 Glutamate dehydrogenase 3 O 2 CC 2 C 2 CCO 2 aketoglutarate ADP ADP Glutamate 5
6 3) 3 O 2 CC 2 C 2 CCO ATP Glutamate Glutamine Synthase Mg O 3 2 CC 2 C 2 CCO 2 Glutamine of glutamine donated to other compounds in synthesis of purines, pyrimidines, and other amino acids 6
7 Amino Acid 1 aketo Acid 2 Amino Acid 2 aketo Acid 1 3 O 2 CC 2 C 2 CCO 2 Glutamate O RCCO 2 Pyridoxal phosphate (PLP) Dependent Aminotransferase O O 2 CC 2 C 2 CCO 2 aketoglutarate 2 RCCO 2 7
8 8
9 CO 2 O CO C 2 OPO 3 2 O CC 2 C 2 CO 2 C C 2 OPO C 3 O 2 CC 2 C 2 CCO 2 2 O 3 C Tautomerization O CO 2 O C 2 2 C 2 OPO 3 2 O 2 CC 2 C 2 CCO 2 O CC 2 C 2 CO 2 C 2 C 2 OPO C 2 O 3 C 9
10 GlutamatePyruvate Aminotransferase (Alanine Transferase ALT) Glutamate Pyruvate Alanine GlutamateOxaloacetate Aminotransferase (Aspartate Transferase AST) aketoglutarate Glutamate aketoglutarate Oxaloacetate Aspartate Blood levels of these aminotransferases, also called transaminases, are important indicators of liver disease 10
11 Essential and onessential Glucogenic and Ketogenic 11
12 ot required in diet Can be formed from aketo acids by transamination and subsequent reactions Alanine Asparagine Aspartate Glutamate Glutamine Glycine Proline Serine Cysteine (from Met*) Tyrosine (from Phe*) * Essential amino acids 12
13 Required in diet umans incapable of forming requisite carbon skeleton Arginine* istidine* Isoleucine Leucine Valine Lysine Methionine Threonine Phenylalanine Tryptophan * Essential in children, not in adults 13
14 Metabolized to aketoglutarate, pyruvate, oxaloacetate, fumarate, or succinyl CoA Phosphoenolpyruvate Glucose Aspartate Asparagine Arginine Phenylalanine Tyrosine Isoleucine Methionine Valine Glutamine Glutamate Proline istidine Alanine Serine Cysteine Glycine Threonine Tryptophan 14
15 Metabolized to acetyl CoA or acetoacetyl CoA Animals cannot convert acetyl CoA or acetoacetyl CoA to pyruvate Isoleucine Leucine * Lysine * Threonine Tryptophan Phenylalanine Tyrosine * Leucine and lysine are only ketogenic 15
16 O O 2 CC 2 C 2 CCO 2 aketoglutarate 3 O 2 CC 2 C 2 CCO 2 Glutamate O Transamination or Glutamate dehydrogenase 3 2 CC 2 C 2 CCO 2 Glutamine Glutamine synthase 5 Steps 4 Steps Guanidino group CO 2 3 Proline 3 C 2 C 2 C 2 CCO 2 Urea Cycle =CC 2 C 2 C 2 CCO 2 Ornithine Arginine 16
17 3 O 2 CC 2 C 2 CCO 2 Glutamate Glutamate decarboxylase CO 2 3 O 2 CC 2 C 2 C 2 Gammaaminobutyrate (GABA) GABA is an important inhibitory neurotransmitter in the brain Drugs (e.g., benzodiazepines) that enhance the effects of GABA are useful in treating epilepsy 17
18 3 O 2 CC 2 C 2 CCO 2 Glutamate Acetylglutamate synthase CoASAc COC 3 O 2 CC 2 C 2 CCO 2 Acetylglutamate Activates 4 Steps 4 CO 3 CPSI Carbamoyl phosphate 2 CO 2 PO C 2 C 2 C 2 CCO 2 Ornithine 3 2 COC 2 C 2 C 2 CCO 2 Citrulline Ureido group Ornithine Transcarbamoylase (OTC) (mitochondria) 18
19 Glucose Glycolysis 3 Steps Pyruvate CO 2 C O C 2 OPO 3 2 3Phosphoglycerate Dehydrogenase AD AD Inhibits CO 2 C=O C 2 OPO 3 2 3Phosphohydroxypyruvate Glutamate Transaminase CO 2 C 3 Phosphatase CO 2 C aketoglutarate 3 C 2 O C 2 OPO 3 2 Serine (Ser) 3Phosphoserine 19
20 Folate Dihydrofolate reductase Key intermediate in biosynthesis of purines and formation of thymine 2 O Tetrahydrofolate (F 4 ) 2 C C 2 C 2 R 5, 10 Methylene F 4 CO 2 C 3 C 2 O CO 2 C 3 Serine Serine hydroxymethyl transferase (PLPdep.) Glycine Important in biosynthesis of heme, porphyrins, and purines 20
21 3 C 3 SC 2 C 2 CCO 2 Methionine (Essential) F 4 Methionine Synthase (Vit. B12dep.) Cystathionine bsynthase (PLPdep.) 3 SC 2 C 2 CCO 2 Lomocysteine CO 2 C 3 C 2 O 5Methyl F 4 Serine O C 3 CC 2 CO 2 bydroxybutyrate 3 SC 2 CCO 2 Cysteine (onessential) Cystathionine lyase C 2 CCO SC 2 C 2 CCO 2 Cystathionine 21
22 omocysteinuria Rare; deficiency of cystathionine bsynthase Dislocated optical lenses Mental retardation Osteoporosis Cardiovascular disease death igh blood levels of homocysteine associated with cardiovascular disease May be related to dietary folate deficiency Folate enhances conversion of homocysteine to methionine 22
23 2 3 C 3 SC 2 C 2 CCO 2 Methionine SAdenosyl methionine synthase ATP O 2 CCC 2 C 2 S 2 C 3 C 3 O Decarboxylated SAM 3 C 2 C 2 C 2 S 2 C 2 O SAM Decarboxylase CO 2 O 2 CCC 2 C 2 S 2 C 3 2 O RC 3 O O R Methyltransferases SAdenosyl Methionine (SAM) C 3 O O SAdenosyl homocysteine O O 23
24 2 3 2 =CC 2 C 2 C 2 CCO 2 Arginine Arginineglycine transamidinase (Kidney) Glycine Ornithine 2 2 =CC 2 CO 2 Guanidoacetate Creatinine (Urine) Creatine C 3 O 2 2 =CC 2 CO 2 C 3 Guanidoacetate Methyltransferase (Liver) onenzymatic (Muscle) Creatine kinase (Muscle) ATP ADP P i SAM ATP SAdenosylhomocysteine ADP PO =CC 2 CO 2 C 3 Phosphocreatine 24
25 Creatine: Dietary supplement Used to improve athletic performance Creatinine: Urinary excretion generally constant; proportional to muscle mass Creatinine Clearance Test: Compares the level of creatinine in urine (24 hrs.) with the creatinine level in the blood Used to assess kidney function Important determinant in dosing of several drugs in patients with impaired renal function 25
26 3 C 2 CCO 2 istidine decarboxylase C 2 C 2 2 istidine CO 2 istamine istamine: Synthesized in and released by mast cells Mediator of allergic response: vasodilation, bronchoconstriction ( 1 receptors) 1 blockers: Diphenhydramine (Benadryl) Loratidine (Claritin) Stimulates secretion of gastric acid ( 2 receptors) 2 blockers: Cimetidine (Tagamet); ranitidine (Zantac) 26
27 Phenylalanine (Essential) 3 C 2 CCO 2 2 O CCC 3 O O Tetrahydrobiopterin (B 4 ) O O 2 2 O Tyrosine (onessential) Phenylalanine4 Monooxygenase (Phenylalanine hydroxylase) 3 C 2 CCO 2 2 O ADP ADP Dihydrobiopterin CCC 3 O O 27
28 ormal Utilization of Phenylalanine Phenylalanine Protein (~25%) Tyrosine (~75%) 28
29 Deficiency of Phe hydroxylase Occurs in 1:20,000 live births in U.S. Seizures, mental retardation, brain damage Treatment: limit phenylalanine intake Screening of all newborns mandated in all states Tyr Phe Transamination O C 2 CCO 2 Phenylpyruvate (urine) 29
30 O O O Tyrosine 3 C 2 CCO 2 Epinephrine (Adrenaline) CC 2 C 3 O SAdenosylhomocysteine Methyl transferase SAM Tyr hydroxylase O O 2 O O Dopamine hydroxylase O O Catechol 3 C 2 CCO 2 Dihydroxyphenylalanine (DOPA) DOPA decarboxylase CO 2 C 2 C 2 2 Dopamine O DOPA, dopamine, norepinephrine, and epinephrine are all neurotransmitters CC 2 2 orepinephrine O 30
31 O Tyrosine 3 C 2 CCO 2 Cleavage of aromatic ring Transamination Deficient in alkaptonuria omogentisate dioxygenase pydroxyphenylpyruvate O O O 2 pydroxyphenylpyruvate dioxygenase (ascorbatedep.) CO 2 O C 2 CCO 2 Fumarate acetoacetate O 2 O C 2 CO 2 omogentisate 31
32 O Tyrosine 3 C 2 CCO 2 Tyr hydroxylase O 2 O O 3 C 2 CCO 2 DOPA Tyrosinase Melanin (Black polymer) ighly colored polymeric intermediates O O C 2 CCO 2 Melanin formed in skin (melanocytes), eyes, and hair In skin, protects against sunlight Albinism: genetic deficiency of tyrosinase 3 Dopaquinone 32
33 Indole ring C 2 CCO 2 Tryptophan (Trp) 3 Trp hydroxylase O 2 O 5ydroxytryptophan 3 C 2 CCO 2 O Decarboxylase CO 2 C 2 C 2 2 5ydroxytryptamine (5T); Serotonin 33
34 Serotonin formed in: Brain (neurotransmitter; regulation of sleep, mood, appetite) Platelets (platelet aggregation, vasoconstriction) Smooth muscle (contraction) Gastrointestinal tract (enterochromaffin cells major storage site) Drugs affecting serotonin actions used to treat: Depression Serotoninselective reuptake inhibitors (SSRI) Migraine Schizophrenia Obsessivecompulsive disorders Chemotherapyinduced emesis Some hallucinogens (e.g., LSD) act as serotonin agonists 34
35 35
36 O C 2 C 2 2 MAO O C 2 CO Serotonin Dehydrogenase C 2 CO 2 O Carcinoid tumors: Malignant GI tumor type Excretion of large amounts of 5IAA 5ydroxyindole acetic acid (5IAA) (Urine) 36
37 O C 2 C Steps 3 CO C 2 C 2 COC 3 Serotonin Melatonin Melatonin: Formed principally in pineal gland Synthesis controlled by light, among other factors Induces skin lightening Suppresses ovarian function Possible use in sleep disorders 37
38 3 C 2 CCO 2 Several steps CO 2 Tryptophan icotinic acid (iacin) icotinamide adenine dinucleotide (AD) 38
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