2-Iminothiolane

2-Iminothiolane
Free base form	Hydrochloride form
Names
	Preferred IUPAC name Thiolan-2-imine
	Other names Traut's reagent; 2-Thiolanimine;
Identifiers
CAS Number	6539-14-6; (HCl): 4781-83-3;
3D model (JSmol)	Interactive image; (HCl): Interactive image;
ChemSpider	10661959; (HCl): 10732937;
EC Number	(HCl): 800-330-2;
PubChem CID	433941; (HCl): 13166855;
UNII	5FP46MY9AM; (HCl): W688HZV733;
CompTox Dashboard (EPA)	DTXSID30984006 ; (HCl): DTXSID60524217;
	InChI InChI=1S/C4H7NS/c5-4-2-1-3-6-4/h5H,1-3H2 Key: CNHYKKNIIGEXAY-UHFFFAOYSA-N; (HCl): InChI=1S/C4H7NS.ClH/c5-4-2-1-3-6-4;/h5H,1-3H2;1H Key: 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 [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 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, though at a much slower rate.^[3]

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

References

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

[Sigma-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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