2-Iminothiolane is a cyclic thioimidate compound also known as Traut's reagent. It is a thiolating reagent that reacts with primary amine groups, such as those of amino acids, to form sulfhydryl groups.
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| Names | |||
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| Preferred IUPAC name
Thiolan-2-imine | |||
Other names
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| Identifiers | |||
| ECHA InfoCard | 100.226.745 | ||
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |||
| C4H7NS C4H7NS·HCl | |||
| Molar mass | 101.17 (free base) 137.63 (HCl)[1] | ||
| Appearance | Powder | ||
| Melting point | 198–201[1] °C (388–394 °F; 471–474 K) (HCl) | ||
| 100 mg/mL (HCl)[1] | |||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Application
edit2-Iminothiolane reacts with primary amines efficiently at pH 7 to 9, creating amidine compounds with a sulfhydryl group. Thus it allows for crosslinking or labeling of molecules such as proteins through use of disulfide or thioether conjugation. It was first used to thiolate a subunit of ribosome in E. coli in 1973 by Robert Traut, its namesake, and his colleagues.[2]
It also reacts with aliphatic and phenolic hydroxyl groups at high pH, albeit at a much slower rate.[3]
References
edit- ^ a b c "2-Iminothiolane hydrochloride". Sigma-Aldrich.
- ^ Traut, R. R.; Bollen, A; Sun, T. T.; Hershey, J. W.; Sundberg, J; Pierce, L. R. (1973). "Methyl 4-mercaptobutyrimidate as a cleavable cross-linking reagent and its application to the Escherichia coli 30S ribosome". Biochemistry. 12 (17): 3266–73. doi:10.1021/bi00741a019. PMID 4581787.
- ^ "Traut's Reagent Instructions" (PDF). Thermo Scientific. Retrieved 2015-07-08.