Metabolism of. Sulfur Containing Amino Acids

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1 Metabolism of Sulfur Containing Amino Acids

2 Methionine S CH 3 CH 2 cysteine CH 2 SH CH 2 CHNH 2 COOH CHNH 2 COOH

3 Essential amino acid Non-polar amio acid Glucogenic amino acid Methionine IMPORTANCE: As a constituent of protein, as well as the initiating amino acid in protein synthesis Source methyl groups for Phosphotidyl choline, DNA, RNA, hormones via conversion of MET to S-adenosyl MET Source sulfur in Cysteine via trans-sulfuration pathway

4 First step: Activation of MET SAM (a high energy compound) Most Reactions with SAM are Methyl transferases Methyl transferred SAM several compounds

5 S-adenosyl methionine, SAM + A adenosyl transferase PPi+Pi A Methionine ATP S-adenosyl methionine,sam

6 SAM is the direct donor of methyl in body RH RH CH 3 adenosyl Methyl transferase A A SAM S adenosyl homocystein homocystein

7 SAM is the methyl donor Phosphatidylethanolamine to phosphatidylcholine Guanidinoacetate to creatine Noreepinephrine to epinephrine Inactivation of catecholamines by catechol-o-methyl transferase, Acetylserotonin to melatonin Methylation of cytosine residues in DNA

8 B12 Regeneration of Met (vitamins: folate+b 12 )

9 SAM Homocysteine (homocys) This represents a branch point in MET metabolism (direction depends on physiological needs of organism). If MET limited homocys remethylated to MET If CYS needed and SAM adequate then homocys transsulfuration pathway.

10 B12 Regeneration of Met (vitamins: folate+b 12 )

11 Vitamin B 12 Deficiency If vitamin B 12 is not available for the synthesis of methylcobalamin, then no acceptor is available for the methyl group of N 5 -methyltetrahydrofolate and metabolic folates become trapped in the N 5 -methyl form.

12 Cysteine Non-essential Glucogenic amino acid Synthesis of Cysteine: SH group from methionine is transferred to serine to form cysteine this is called transsulfuration reaction

13 Trans-Sulfuration Pathway Both reactions use pyridoxal phosphate as a cofactor

14 Cystine Formation SH CH 2 CH NH 2 COOH cysteine SH CH 2 + CH NH 2 COOH cysteine 2H 2H S S CH 2 CH 2 CH NH 2 CH NH 2 COOH COOH cystine

15 Keeping Correct Structure of Proteins Cysteine residues in polypeptide chain form disulfide bridges to make stabilize structure of proteins e.g Insulin

16 Type I Homocystinuria B6 responsive - (responsive to vitamin therapy) - 50% Type I - doses B6 up to 1 g / day Remember defect in cystathionine synthase Enzyme that converts homocys CYS (Step I) Pyridoxal phosphate is a cofactor B6 pyridoxal phosphate

17 B12 Regeneration of Met (vitamins: folate+b 12 )

18 B6 unresponsive Type II Homocystinuria Enzyme mutation that does not involve cofactor binding site Therefore dietary therapy THF Why? Enhance alternate pathway keep MET (use plant protein like soybean/lentil which has half the MET of animal protein) CYS conditionally essential because MET cannot be converted to CYS Start therapy early due to serious clinical symptoms

19 Hyperhomocysteinemia can results in: Vascular diseases, endothelial dysfunction, atherosclerosis, thrombophilia Skeletal anomalies retardation of mental development Ectopic lens Alzheimer's disease Kidneys insufficiency Colorectal cancer

20 Trans-Sulfuration Pathway Both use pyridoxal phosphate as a cofactor

21 Cystathioninuria Due to a defect in cystathionase (Step 2 CYS synthesis) Less clinical abnormalities than Type I Accumulation cystathionine in blood/urine (not detectable normally)

22 Cystinuria Inheritance: Autosomal recessive defect of intestinal absorption and proximal tubular reabsorption transport system Symptoms: All four amino acids appear in the urine.

23 Cystinosis Inheritance: Autosomal recessive Defect: Deposition of cystine crystals in lysosomes Accumulates in liver, bone marrow, spleen, WBC, cornea, kidney

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