2-Iminothiolane

2-Iminothiolane
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Names
IUPAC name
Dihydro-2(3H)-thiophenimine hydrochloride
Other names
  • Traut's reagent
  • 2-Thiolanimine hydrochloride
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]

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

References

  1. 1 2 3 Sigma-Aldrich Co., product no. I6256. Retrieved on July 06, 2015.
  2. ↑ 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.
  3. ↑ "Traut's Reagent Instructions" (PDF). Thermo Scientific. Retrieved 2015-07-08.
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