Hydroxy amino acids

Introduction of Hydroxy amino acids

Introduction of Serine (Hydroxy amino acids)

  • Aliphatic hydroxy amino acid.
  • Non essential amino acid.
  • Glucogenic.
  • Isolated by Cramer in 1865.

Serine Biosynthesis (Hydroxy amino acids)

  • The main pathway to serine starts with the glycolytic intermediate 3-phosphoglycerate.
  • An NADH-linked dehydrogenase converts 3-phosphoglycerate into a keto acid, 3-phosphopyruvate, suitable for subsequent transamination. 
  • Aminotransferase activity with glutamate as a donor produces 3-phosphoserine, which is converted to serine by phosphoserine phosphatase. 

Serine Catabolism

  • The conversion of serine to glycine and then glycine oxidation to CO2 and NH3, with the production of two equivalents of N5, N10-methyleneTHF. 
  • Serine can also be converted to pyruvate through a deamination reaction catalyzed by serine dehydratase

Functions of Serine

  • Serine is involved in many anabolic reactions including the synthesis of
    • Glycine
    • Cysteine
    • Ethanolamine 
    • Phospholipid 
    • Sphingophospholipids
    • One carbon metabolism
    • Selenocysteine
    • Drugs
      • Azaserine
      • Cycloserine

Threonine (Hydroxy amino acids)

The –OH group of threonine is a site for protein phosphorylation

Threonine Catabolism

SULPHUR CONTAINING AMINO ACIDS

Metabolism of Sulfur-containing AAs

METABOLISM OF METHIONINE

  • Essential Glucogenic Amino Acid
  • Catabolism: via being homocysteine, which is converted into homoserine (Trans-Sulfuration) and then ultimately into propionyl CoA Succinyl CoA.
  • Function:

Trans-Methylation:  is achieved by its role in      formation of SAM  by Methyl transferase.

–  Polyamines synthesis.

– Cysteine  synthesis and its derivatives.

  • Methionine metabolism may be divided in to three parts 
  1. Utilization of Methionine for transmethylation reactions.
  2. Conversion of Methionine to Cysteine and Cystine.
  3. Degradation of Cysteine and its conversion to specialized products. 

TRANSMETHYLATION

  • The transfer of methyl group (-CH3) from active methionine to an acceptor is known as transmethylation.
  • Methionine has to be activated to S-adenosyl methionine or active methionine to donate the methyl group

Synthesis of S-Adenosylmethionine

  1. The synthesis of S-adenosylmethionine occurs by the transfer of an adenosyl group from ATP to sulfur atom of Methionine.
  2. This reaction is catalyzed by Methionine S-adenosyl transferase.

Condensation of ATP and methionine yield S-adenosylmethionine (SAM)

SAM serves as a precursor for numerous methyl transfer reactions (e.g. the conversion of norepinephrine to epinephrine).

Functions of S-adenosylmethionine (SAM)

  1. The SAM is highly reactive due to the presence of a positive charge.
  2. The enzymes involved in the transfer of methyl group are collectively known as methyltransferases.
  3. SAM is the direct donor of methyl in body. Methylation can synthesize many important materials such as: choline, creatine, etc.
  4.   SAM is also involved in the    synthesis of polyamines

Significance of Transmethylation

  • Many compounds become active only after Methylation.
  • Protein methylation helps to control protein turn over.
  • In general, methylation protects the protein from immediate degradation.

Methionine Degradation 

S-adenosylmethionine (SAM) – a common methyl donor in the cell 

Cysteine

•Non-Essential Glucogenic Amino Acid

Cysteine Biosynthesis

  • Catabolism: Into pyruvate
  • Significance of Cysteine Metabolism:
    • GSH
    • Taurine
    • Cystine
    • PAPS

FORMATION OF GLUTATHIONE

  • Glutathione is a tripeptide of glutamate, cysteine and glycine.
  • • Glutathione is generally abbreviated as GSH.

Formation of PAPS

Synthesis of cystine

Homocysteine and Heart attacks

  • Homocysteine is an intermediate in the Synthesis of cysteine from methionine.
  • It is believed that homocysteine reacts with collagen to produce reactive free radicals, besides interfering with collagen cross links.
  • Homocysteine is also involved in the aggregation of LDL particles.
  • All this leads to an increase tendency
  • For atherogenesis, and consequently Heart complications. 

Homocysteine (< 15 μmol/L)

Hyperhomocysteinemia can results in:

  • Vascular diseases, endothelial dysfunction, atherosclerosis
  • Skeletal anomalies
  • retardation of mental development
  • Alzheimer’s disease
  • Kidneys insufficiency
  • Colorectal cancer

Inborn error of  Sulfur containing Amino Acids

Cystinuria

  • One of the most common inherited disease with a frequency of 1 in 7, 000.
  • Cystinuria is usually identified in the laboratory by cyanide nitroprusside test.
  • Aminoacidopathy (Not a metabolic disorder) 
  • Caused by:

Defective renal re- absorption of dibasic amino acid 

Clinically:

  • Cystine precipitation  Renal cystine stones

Treatment:

    – Alkalanization of urine by Na2CO3

    – Plenty of fluids 

    -D-penicillamine, captopril drugs can be used

Cystinosis

  • Also known as cysteine storage disease. 
  • Cysteine crystals are deposited in lysosomes of many tissues and organs of reticuloendothelial system through out the body.
  • These include spleen, lymph nodes, liver, Kidney, bone marrow etc.
  • Abnormality in the transport across lysosomal membranes

Homocystinuria

  • First Described in 1962, these are the latest in the series of inborn error of metabolism.
  • All of them are autosomal recessive conditions.
  • Incidence is 1 in 200, 000 birth.
  • Normal homocysteine level in blood is 5-15 micromol/liter.
  • In disease it may be increased to 50 – 100 times.
  • Homocystinuria is an inborn error of aminoacid metabolism in which accumulation and excretion of large amounts of homocysteine and SAM are seen
  • Homocystinuria type I, due to deficiency of the enzyme cystathionine synthase, is the most common inborn error of methionine metabolism. It is characterized by mental retardation, lens dislocation, skeletal abnormalities and thrombotic vascular disease.
  • Homocystinuria may also be due to defects in methyl cobalamin formation, i.e., Homocystinuria type II, characterized by the triad of megaloblastic anemia, homo-cystinuria and hypomethioninemia. 
  • Deficiency of the enzyme methyltetra-hydrofolate reductase, results in homo cystinuria type III, which is characterized by homocystinuria and homocystinemia with low or normal blood methionine levels.

Treatment

Diet low in methionine and rich in cysteine

Other Biochemistry Notes

Biochemistry of Proteins

Carbohydrate Metabolism

VITAMIN PYRIDOXINE AND BIOTIN

Vitamin A

VITAMIN D

Pyrimidine metabolism

Purine Metabolism

Cardiac Biomarkers

. Blood Metabolism (Heme synthesis and breakdown)

Haemoglobinopathies

DNA Repair

Regulation of gene expression

DNA Replication

Transcription

Protein synthesis and genetic code

Detoxification (Xenobiotics)

Liver Function Test

Transamination Deamination & Urea Cycle

METABOLISM OF INDIVIDUAL AMINO ACIDS

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