Amino Acids M t b liA i A id Metabolism١   Prof Dr Mohammad Ibrahim Prof of Medical Biochemistry            http://osp.man...
•       Alanine    •       β- Alanine٢       Prof Dr Mohammad Ibrahim Prof of Medical Biochemistry                http://o...
Alanine                                                     NH2                                            CH 3     CH COO...
AlanineBiosynthesis 1.   From    pyruvic acid 2.   From   serine 3. 3    From   cysteine 4.   From   tyrosine 5.   From   ...
AlanineBiosynthesis                 Glutamic acid          α ketoglutaric        O                                        ...
AlanineMetabolic Fate1.   Incorporated in protein structure2.2    Formation f Pyruvic acid     F m ti of P        i   id3....
Alanine2- Formation of pyruvic acid A- Transamination            α ketoglutaric                                         Gl...
Alanine3- Glucose biosynthesis                α ketoglutaric                      g             Glutamic acid    Alanine  ...
Alanine 4- Glucose alanine cycle  Liver                   Blood              Muscle           Glucose           Glucose   ...
β AlanineStructure formula            NH2                  NH 2                       CH 3 CH COOH               CH 2 CH2 ...
β Alanine1- Biocynthesis from aspartic acid                                                     NH2                    β D...
β Alanine    2-Bisynthesis from pyrimidine catabolism         NH 2                  O                                     ...
β Alanine 3-Bisynthesis from carnosine      NH2      CH2 CH2 C O       Carnosinase            NH 2              NH        ...
β AlanineMetabolic Fate 1. Enters in the structure of: 1 E t     i th t      t     f     • pantothenic acid       p     • ...
Biosynthesis of carnosine and anserine    y                                                        NH2  β Alanine         ...
β Alanyl histidine dipeptides      y•    activate myosin ATPase,•    enhance copper uptake.•    buffer the pH of anaerobic...
β Alanine β-Alanine catabolismNH 2                      O                          O              Deamination             ...
Non α amino acids1.   β Alaninie2.   β Aminoisobutyric acid3.3    γ Aminobutyric acid (GABA)4.   δ Aminolevulinic acid١٨  ...
Non protein amino acids1.   β Alaninie2.2    β A i i b t i acid       Aminoisobutyric     id3.   γ Aminobutyric acid (GABA...
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03 alanine metabolism

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03 alanine metabolism

  1. 1. Amino Acids M t b liA i A id Metabolism١ Prof Dr Mohammad Ibrahim Prof of Medical Biochemistry http://osp.mans.edu.eg/medbiochem_mi
  2. 2. • Alanine • β- Alanine٢ Prof Dr Mohammad Ibrahim Prof of Medical Biochemistry http://osp.mans.edu.eg/medbiochem_mi
  3. 3. Alanine NH2 CH 3 CH COOHStructure • It is α-amino propionic acid p pNutrional Value • It is non-essential amino acidMetabolic Fate • It is glucogenic amino acid g g٣ Prof Dr Mohammad Ibrahim Prof of Medical Biochemistry http://osp.mans.edu.eg/medbiochem_mi
  4. 4. AlanineBiosynthesis 1. From pyruvic acid 2. From serine 3. 3 From cysteine 4. From tyrosine 5. From tryptophan 6. From aspartic acid٤ Prof Dr Mohammad Ibrahim Prof of Medical Biochemistry http://osp.mans.edu.eg/medbiochem_mi
  5. 5. AlanineBiosynthesis 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 Tryptophan3 phospho glycerate Glycine Phenyl alanine Hydroxy Threonine CholineGlycerol proline ٥ Prof Dr Mohammad Ibrahim Prof of Medical Biochemistry http://osp.mans.edu.eg/medbiochem_mi
  6. 6. AlanineMetabolic Fate1. Incorporated in protein structure2.2 Formation f Pyruvic acid F m ti of P i id3. Synthesis of glucose y g4. Glucose alanine cycle٦ Prof Dr Mohammad Ibrahim Prof of Medical Biochemistry http://osp.mans.edu.eg/medbiochem_mi
  7. 7. Alanine2- Formation of pyruvic acid A- Transamination α ketoglutaric Glutamic acid NH2 PLP OCH 3 CH COOH CH 3 C COOH Aminotransferase (ALT) (GPT) B- Oxidative deamination H2O FMN FMNH2 NH 3 NH2 OCH 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. 8. Alanine3- Glucose biosynthesis α ketoglutaric g Glutamic acid Alanine PLP Pyruvic acid Aminotransferase Glucose٨ Prof Dr Mohammad Ibrahim Prof of Medical Biochemistry http://osp.mans.edu.eg/medbiochem_mi
  9. 9. Alanine 4- Glucose alanine cycle Liver Blood Muscle Glucose Glucose Glucose NADH.H+ NAD Pyruvic Pyruvic Lactic Glutamic Glutamic α Ketoglutaricα Ketoglutaric g Alanine Alanine Alanine ٩ Prof Dr Mohammad Ibrahim Prof of Medical Biochemistry http://osp.mans.edu.eg/medbiochem_mi
  10. 10. β AlanineStructure formula NH2 NH 2 CH 3 CH COOH CH 2 CH2 COOH α Alanine β AlanineBiosynthesis 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. 11. β Alanine1- 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 Alanine١١ Prof Dr Mohammad Ibrahim Prof of Medical Biochemistry http://osp.mans.edu.eg/medbiochem_mi
  12. 12. β Alanine 2-Bisynthesis from pyrimidine catabolism NH 2 O NH 2 N Deaminase HN C O NH CH 2 CH 2 COOHO N O N β urido propionic H NH3 H 2H H2OCytosine 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. 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 AlanineHN 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. 14. β AlanineMetabolic 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 CoA١٤ Prof Dr Mohammad Ibrahim Prof of Medical Biochemistry http://osp.mans.edu.eg/medbiochem_mi
  15. 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 CH3HN N CarnosineHistidine 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. 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 spasticity١٦ Prof Dr Mohammad Ibrahim Prof of Medical Biochemistry http://osp.mans.edu.eg/medbiochem_mi
  17. 17. β Alanine β-Alanine catabolismNH 2 O O Deamination D i i DecarboxylationCH 2 CH2 COOH CH CH2 COOH CH CH3B 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. 18. Non α amino acids1. β Alaninie2. β Aminoisobutyric acid3.3 γ Aminobutyric acid (GABA)4. δ Aminolevulinic acid١٨ Prof Dr Mohammad Ibrahim Prof of Medical Biochemistry http://osp.mans.edu.eg/medbiochem_mi
  19. 19. Non protein amino acids1. β Alaninie2.2 β A i i b t i acid Aminoisobutyric id3. γ Aminobutyric acid (GABA)4. δ Aminolevulinic acid l l d5. α Amino β ketoadepic acid6. α Amino β ketobutyric acid7. Ornithine8. Citrulline١٩ Prof Dr Mohammad Ibrahim Prof of Medical Biochemistry http://osp.mans.edu.eg/medbiochem_mi
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