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Homocysteine thiolactone (HTL) is an organosulfur compound with the formula H 2 NCHC(O)SCH 2 CH 2. It is the thiolactone (intramolecular thioester ) of homocysteine . It is produced by methionyl-tRNA synthetase in an error-editing reaction that prevents translational incorporation of homocysteine into proteins .
Homocysteine can cyclize to give homocysteine thiolactone, a five-membered heterocycle. Because of this "self-looping" reaction, homocysteine-containing peptides tend to cleave themselves by reactions generating oxidative stress. [12] Homocysteine also acts as an allosteric antagonist at Dopamine D 2 receptors. [13]
The activation of the drug clopidogrel (top left) gives a thiolactone, which ring-opens. [3] Thiolactones are intermediates in the activation of some drugs. [4] In nature, the most common thiolactone is homocysteine thiolactone. It is produced from homocysteine. It may play a role in protein damage. [5]
As a consequence of the biochemical reactions in which homocysteine is involved, deficiencies of vitamin B 6, folic acid (vitamin B 9), and vitamin B 12 can lead to high homocysteine levels. [2] Other possible causes of hyperhomocysteinemia include genetics, excessive methionine intake, and other diseases.
Reaction 5 is catalyzed by cystathionine beta-synthase while reaction 6 is catalyzed by cystathionine gamma-lyase. The required homocysteine is synthesized from methionine in reactions 1, 2, and 3. The transsulfuration pathway is a metabolic pathway involving the interconversion of cysteine and homocysteine through the intermediate cystathionine.
Transmethylation is a biologically important organic chemical reaction in which a methyl group is transferred from one compound to another. An example of transmethylation is the recovery of methionine from homocysteine. In order to sustain sufficient reaction rates during metabolic stress, this reaction requires adequate levels of vitamin B 12 ...
The cold water can cause heart attack due to severe vasoconstriction, [2] where the heart has to work harder to pump the same volume of blood throughout the arteries. For people with pre-existing cardiovascular disease , the additional workload can result in myocardial infarction and/or acute heart failure , which ultimately may lead to a ...
Methylenetetrahydrofolate reductase deficiency is the most common genetic cause of elevated serum levels of homocysteine (hyperhomocysteinemia). It is caused by genetic defects in MTHFR, which is an important enzyme in the methyl cycle. [1] Common variants of MTHFR deficiency are asymptomatic and have only minor effects on disease risk. [2]