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From Wikipedia, the free encyclopedia
Thiolactones are a class of heterocyclic compounds in organic chemistry. They are analogs of the more common lactones in which an oxygen atom is replaced with a sulfur atom. The sulfur atom is within the ring system and adjacent to a carbonyl group.
Thiolactones can be prepared by dehydration of thiol-containing carboxylic acids. Thiolactones can be hydrolyzed back to the thiol acids under basic conditions.[1] β-Thiolactones can be opened by reaction at the 4-position via SN2 nucleophilic reactions.[2]
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] The drugs citiolone and erdosteine are modified versions of homocysteine thiolactone.
Thiolactones have been found in peptides synthesized by bacteria such as Staphylococcus aureus in order to regulate their quorum-sensing system.[6]
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