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2-Iminothiolane

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(Redirected from Traut's reagent)
2-Iminothiolane
2-IminothiolaneFree base form 2-Iminothiolane HydrochlorideHydrochloride form
Names
Preferred IUPAC name Thiolan-2-imine
Other names
  • Traut's reagent
  • 2-Thiolanimine
Identifiers
CAS Number
ECHA InfoCard 100.226.745 Edit this at Wikidata
PubChem CID
CompTox Dashboard (EPA)
Properties
Chemical formula C4H7NS
C4H7NS·HCl
Molar mass 101.17 (free base)
137.63 (HCl)
Appearance Powder
Melting point 198–201 °C (388–394 °F; 471–474 K) (HCl)
Solubility in water 100 mg/mL (HCl)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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 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.

It also reacts with aliphatic and phenolic hydroxyl groups at high pH, albeit at a much slower rate.

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

References

  1. ^ "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.
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