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2-Iminothiolane

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2-Iminothiolane
2-Iminothiolane
Free base form
2-Iminothiolane Hydrochloride
Names
Preferred IUPAC name
Thiolan-2-imine
Other names
  • Traut's reagent
  • 2-Thiolanimine
Identifiers
ECHA InfoCard 100.226.745 Edit this at Wikidata
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).

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

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2-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]

The reaction of 2-iminothiolane with an amine group of a peptide.

References

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  1. ^ a b c "2-Iminothiolane hydrochloride". Sigma-Aldrich.
  2. ^ 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.
  3. ^ "Traut's Reagent Instructions" (PDF). Thermo Scientific. Retrieved 2015-07-08.