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
[edit]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
[edit]
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]
See also
[edit]References
[edit]- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.