2-Iminothiolane
Chemical compound
From Wikipedia, the free encyclopedia
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.
| |||
| Names | |||
|---|---|---|---|
| Preferred IUPAC name
Thiolan-2-imine | |||
Other names
| |||
| Identifiers | |||
3D model (JSmol) |
|||
| ChemSpider | |||
| EC Number |
| ||
PubChem CID |
|||
| UNII |
| ||
CompTox Dashboard (EPA) |
| ||
| |||
| |||
| 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).
| |||
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]
