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03 alanine metabolism
- 1. Amino Acids M t b li A i A id Metabolism ١ Prof Dr Mohammad Ibrahim Prof of Medical Biochemistry http://osp.mans.edu.eg/medbiochem_mi
- 2. • Alanine • β- Alanine ٢ Prof Dr Mohammad Ibrahim Prof of Medical Biochemistry http://osp.mans.edu.eg/medbiochem_mi
- 3. Alanine NH2 CH 3 CH COOH Structure • It is α-amino propionic acid p p Nutrional Value • It is non-essential amino acid Metabolic Fate • It is glucogenic amino acid g g ٣ Prof Dr Mohammad Ibrahim Prof of Medical Biochemistry http://osp.mans.edu.eg/medbiochem_mi
- 4. Alanine Biosynthesis 1. From pyruvic acid 2. From serine 3. 3 From cysteine 4. From tyrosine 5. From tryptophan 6. From aspartic acid ٤ Prof Dr Mohammad Ibrahim Prof of Medical Biochemistry http://osp.mans.edu.eg/medbiochem_mi
- 5. Alanine Biosynthesis Glutamic acid α ketoglutaric O NH2 CH 3 C COOH PLP CH 3 CH COOH Aminotransferase Pyruvic (ALT) Alanine (GPT) Glucose Serine Cysteine Aspartic Tyrosine Tryptophan 3 phospho glycerate Glycine Phenyl alanine Hydroxy Threonine Choline Glycerol proline ٥ Prof Dr Mohammad Ibrahim Prof of Medical Biochemistry http://osp.mans.edu.eg/medbiochem_mi
- 6. Alanine Metabolic Fate 1. Incorporated in protein structure 2. 2 Formation f Pyruvic acid F m ti of P i id 3. Synthesis of glucose y g 4. Glucose alanine cycle ٦ Prof Dr Mohammad Ibrahim Prof of Medical Biochemistry http://osp.mans.edu.eg/medbiochem_mi
- 7. Alanine 2- Formation of pyruvic acid A- Transamination α ketoglutaric Glutamic acid NH2 PLP O CH 3 CH COOH CH 3 C COOH Aminotransferase (ALT) (GPT) B- Oxidative deamination H2O FMN FMNH2 NH 3 NH2 O CH 3 CH COOH CH 3 C COOH L amino acid oxidase ٧ Prof Dr Mohammad Ibrahim Prof of Medical Biochemistry http://osp.mans.edu.eg/medbiochem_mi
- 8. Alanine 3- Glucose biosynthesis α ketoglutaric g Glutamic acid Alanine PLP Pyruvic acid Aminotransferase Glucose ٨ Prof Dr Mohammad Ibrahim Prof of Medical Biochemistry http://osp.mans.edu.eg/medbiochem_mi
- 9. Alanine 4- Glucose alanine cycle Liver Blood Muscle Glucose Glucose Glucose NADH.H+ NAD Pyruvic Pyruvic Lactic Glutamic Glutamic α Ketoglutaric α Ketoglutaric g Alanine Alanine Alanine ٩ Prof Dr Mohammad Ibrahim Prof of Medical Biochemistry http://osp.mans.edu.eg/medbiochem_mi
- 10. β Alanine Structure formula NH2 NH 2 CH 3 CH COOH CH 2 CH2 COOH α Alanine β Alanine Biosynthesis y 1. From Aspartic acid p 2. From pyrimidine catabolism 3. From carnosine ١٠ Prof Dr Mohammad Ibrahim Prof of Medical Biochemistry http://osp.mans.edu.eg/medbiochem_mi
- 11. β Alanine 1- Biocynthesis from aspartic acid NH2 β Decarboxylation COOH CH 3 CH COOH CH 2 CO2 α Alanine CH NH 2 NH 2 COOH α Decarboxylation CH 2 CH2 COOH Aspartic CO2 β Alanine ١١ Prof Dr Mohammad Ibrahim Prof of Medical Biochemistry http://osp.mans.edu.eg/medbiochem_mi
- 12. β Alanine 2-Bisynthesis from pyrimidine catabolism NH 2 O NH 2 N Deaminase HN C O NH CH 2 CH 2 COOH O N O N β urido propionic H NH3 H 2H H2O Cytosine Uracil H2O NH3 CO2 NH 2 CH 2 CH2 COOH β Alanine ١٢ Prof Dr Mohammad Ibrahim Prof of Medical Biochemistry http://osp.mans.edu.eg/medbiochem_mi
- 13. β Alanine 3-Bisynthesis from carnosine NH2 CH2 CH2 C O Carnosinase NH 2 NH CH 2 CH2 COOH CH2 CH COOH H2O β Alanine HN N + NH2 Carnosine CH2 CH COOH HN N Histidine ١٣ Prof Dr Mohammad Ibrahim Prof of Medical Biochemistry http://osp.mans.edu.eg/medbiochem_mi
- 14. β Alanine Metabolic Fate 1. Enters in the structure of: 1 E t i th t t f • pantothenic acid p • CoASH 2. 2 Forms dipeptides with histidine: • Carnosine • Anserine 3. 3 Catabolized to acetyl CoA ١٤ Prof Dr Mohammad Ibrahim Prof of Medical Biochemistry http://osp.mans.edu.eg/medbiochem_mi
- 15. Biosynthesis of carnosine and anserine y NH2 β Alanine ATP ADP+Pi CH2 CH2 C O NH 2 NH CH 2 CH2 COOH CH2 CH COOH + NH2 H2O HN N CH2 CH COOH CH3 HN N Carnosine Histidine NH2 CH2 CH2 C O NH CH2 CH COOH N N Ansirine CH 3 ١٥ Prof Dr Mohammad Ibrahim Prof of Medical Biochemistry http://osp.mans.edu.eg/medbiochem_mi
- 16. β Alanyl histidine dipeptides y • activate myosin ATPase, • enhance copper uptake. • buffer the pH of anaerobically contracting skeletal muscle. • Hydrolysis of carnosine is catalyzed by carnosinase carnosinase. • Carnosinase deficiency is characterized by – Carnosinosis – C Carnosinuria i i – Muscle spasticity ١٦ Prof Dr Mohammad Ibrahim Prof of Medical Biochemistry http://osp.mans.edu.eg/medbiochem_mi
- 17. β Alanine β-Alanine catabolism NH 2 O O Deamination D i i Decarboxylation CH 2 CH2 COOH CH CH2 COOH CH CH3 B Alanine NH3 Malonic semialdehyde CO Acetaldehyde 2 Oxidation Oxidation HOOC CH 2 COOH CH 3 COOH Malonic acid Acetic acid CoA.SH CoA.SH Thiokinase Thiokinase H2O H2O HOOC CH 2 CO-S.CoA CH 3 CO-S.CoA Malonyl CoA y Acetyl CoA ١٧ Prof Dr Mohammad Ibrahim Prof of Medical Biochemistry http://osp.mans.edu.eg/medbiochem_mi
- 18. Non α amino acids 1. β Alaninie 2. β Aminoisobutyric acid 3. 3 γ Aminobutyric acid (GABA) 4. δ Aminolevulinic acid ١٨ Prof Dr Mohammad Ibrahim Prof of Medical Biochemistry http://osp.mans.edu.eg/medbiochem_mi
- 19. Non protein amino acids 1. β Alaninie 2. 2 β A i i b t i acid Aminoisobutyric id 3. γ Aminobutyric acid (GABA) 4. δ Aminolevulinic acid l l d 5. α Amino β ketoadepic acid 6. α Amino β ketobutyric acid 7. Ornithine 8. Citrulline ١٩ Prof Dr Mohammad Ibrahim Prof of Medical Biochemistry http://osp.mans.edu.eg/medbiochem_mi