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2-Iminothiolane

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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
3D model (JSmol)
ChemSpider
EC Number
  • (HCl): 800-330-2
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4H7NS/c5-4-2-1-3-6-4/h5H,1-3H2Key: CNHYKKNIIGEXAY-UHFFFAOYSA-N
  • (HCl): InChI=1S/C4H7NS.ClH/c5-4-2-1-3-6-4;/h5H,1-3H2;1HKey: ATGUDZODTABURZ-UHFFFAOYSA-N
SMILES
  • C1CC(=N)SC1
  • (HCl): C1CC(=N)SC1.Cl
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, though 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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