Thiolactone

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.

Chemistry

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]

Occurrence

The most common thiolactone, homocysteine thiolactone is produced biochemically from homocysteine and it may play a role in protein damage.[3] The thiolactone functional group is also present in some pharmaceutical drugs such as citiolone and erdosteine.

References

  1. ^ Stevens, Charles M.; Tarbell, D. Stanley (1954). Journal of Organic Chemistry 19 (12): 1996–2003. doi:10.1021/jo01377a017. 
  2. ^ Crich, David; Sana, Kasinath (2009). "SN2-Type Nucleophilic Opening of β-Thiolactones (Thietan-2-ones) as a Source of Thioacids for Coupling Reactions". The Journal of Organic Chemistry 74 (9): 3389–3393. doi:10.1021/jo9001728. PMID 19388715. 
  3. ^ Jakubowski, H (2000). "Homocysteine thiolactone: Metabolic origin and protein homocysteinylation in humans". The Journal of nutrition 130 (2S Suppl): 377S–381S. PMID 10721911.