2-Iminothiolane
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Names | |||
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IUPAC name
Dihydro-2(3H)-thiophenimine hydrochloride | |||
Other names
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Identifiers | |||
4781-83-3 (Hydrochloride) | |||
ECHA InfoCard | 100.226.745 | ||
PubChem | 13166855 | ||
Properties | |||
C4H7NS·HCl | |||
Molar mass | 137.63 (Hydrochloride)[1] 101.17 (Free base) | ||
Appearance | Powder | ||
Boiling point | 198–201[1] °C (388–394 °F; 471–474 K) (Hydrochloride) | ||
100 mg/mL[1] | |||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |||
Infobox references | |||
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.
Application
2-Iminothiolane reacts witih primary amines efficienty at pH 7 to 9, creating aminidine 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
- 1 2 3 Sigma-Aldrich Co., product no. I6256. Retrieved on July 06, 2015.
- ↑ R. R. Traut et al., Methyl 4-mercaptobutyrimidate as a cleavable cross-linking reagent and its application to the Escherichia coli 30S ribosome, Biochemistry 12, 1973, pp. 3266–3273, PMID 4581787.
- ↑ "Traut's Reagent Instructions" (PDF). Thermo Scientific. Retrieved 2015-07-08.
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