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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]
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 ...
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Water-reactive substances [1] are those that spontaneously undergo a chemical reaction with water, often noted as generating flammable gas. [2] Some are highly reducing in nature. [ 3 ] Notable examples include alkali metals , lithium through caesium , and alkaline earth metals , magnesium through barium .