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Thiolactone

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α-, β-, γ-, and δ-lactones (left to right)

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. β-Thiolactones can be opened by reaction at the 4-position via SN2 nucleophilic reactions.

Occurrence

The activation of the drug clopidogrel (top left) gives a thiolactone, which ring-opens.

Thiolactones are intermediates in the activation of some drugs.

In nature, the most common thiolactone is homocysteine thiolactone. It is produced from homocysteine. It may play a role in protein damage. 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.

See also

References

  1. Stevens, Charles; Tarbell, D. Stanley (December 1954). "The Kinetics of Basic Hydrolysis Of Some γ-Lactones and γ-Thiolactones In Aqueous Acetone". The 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. Pereillo JM, Maftouh M, Andrieu A, Uzabiaga MF, Fedeli O, Savi P, Pascal M, Herbert JM, Maffrand JP, Picard C (2002). "Structure and stereochemistry of the active metabolite of clopidogrel". Drug Metab. Dispos. 30 (11): 1288–95. doi:10.1124/dmd.30.11.1288. PMID 12386137. S2CID 2493588.
  4. Farid, Nagy A.; Kurihara, Atsushi; Wrighton, Steven A. (2010). "Metabolism and Disposition of the Thienopyridine Antiplatelet Drugs Ticlopidine, Clopidogrel, and Prasugrel in Humans". The Journal of Clinical Pharmacology. 50 (2): 126–142. doi:10.1177/0091270009343005. PMID 19948947.
  5. Jakubowski, H (2000). "Homocysteine thiolactone: Metabolic origin and protein homocysteinylation in humans". The Journal of Nutrition. 130 (2S Suppl): 377S–381S. doi:10.1093/jn/130.2.377S. PMID 10721911.
  6. Malone, C.L (2007). "Biosynthesis of Staphylococcus aureus Autoinducing Peptides by using the Synechocystis DnaB Mini-Intein". Applied and Environmental Microbiology. 73 (19): 6036–6044. Bibcode:2007ApEnM..73.6036M. doi:10.1128/aem.00912-07. PMC 2074992. PMID 17693565.
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