In organic chemistry, hemithioacetals (or thiohemiacetals) are organosulfur compounds with the general formula R−CH(−OH)−SR’. They are the sulfur analogues of the acetals, R−CH(−OH)−OR’, with an oxygen atom replaced by sulfur (as implied by the thio- prefix). Because they consist of four differing substituents on a single carbon, hemithioacetals are chiral. A related family of compounds are the dithiohemiacetals, with the formula R−CH(−SH)−SR’.[1] Although they can be important intermediates, hemithioacetals are usually not isolated, since they exist in equilibrium with thiols (−SH) and aldehydes (−CH=O).
^IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "thiohemiacetals". doi:10.1351/goldbook.T06355
In organic chemistry, hemithioacetals (or thiohemiacetals) are organosulfur compounds with the general formula R−CH(−OH)−SR’. They are the sulfur analogues...
detoxified by glutathione. Glutathione reacts with methylglyoxal to give a hemithioacetal, which converted into S-D-lactoyl-glutathione by glyoxalase I. This...
reactions proceed via the intermediacy of hemithioacetals (R−CH(−OH)−SR'): Thiol addition to give hemithioacetal: RSH + R ′ CH ( O ) ⟶ R ′ CH ( SR ) OH {\displaystyle...
4.4.1.5, also known as glyoxalase I) catalyzes the isomerization of hemithioacetal adducts, which are formed in a spontaneous reaction between a glutathionyl...
glyoxalase І, which catalyzes the isomerization of the spontaneously formed hemithioacetal adduct between glutathione and 2-oxoaldehydes (such as methylglyoxal)...
clinically effective. Instead, alternative chemicals such as sulfanegen, the hemithioacetal cyclic dimer of 3-MP, are being evaluated that produce 3-MP in vivo...
lyase. Prenylcysteine oxidase 1, symbol PCYOX1, gene on chromosome 2 Hemithioacetals in nature, for mechanism of action Flavin adenine dinucleotide, cofactor...
lactoylglutathione ligase, is an enzyme catalyzing isomerization of hemithioacetal adducts. These results explain that MROH9 function may depend on the...
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