{{Chembox | Name = 2-Iminothiolane | Reference = | PIN = Thiolan-2-imine | SystematicName = | OtherNames = {{Unbulleted list | Traut's reagent | 2-Thiolanimine }} | ImageFileL1 = 120px|2-Iminothiolane | ImageFileR1 = 168px|2-Iminothiolane Hydrochloride | ImageCaptionL1 = Free base form | ImageCaptionR1 = Hydrochloride form <!-- Sections --> |Section1={{Chembox Identifiers | index1_label = (HCl) | CASNo = 6539-14-6 | CASNo1 = 4781-83-3 | ChemSpiderID = 10661959 | ChemSpiderID1 = 10732937 | DTXSID1 = DTXSID60524217 | EC_number1 = 800-330-2 | PubChem = 433941 | PubChem1 = 13166855 | UNII = 5FP46MY9AM | UNII1 = W688HZV733 | StdInChI=1S/C4H7NS/c5-4-2-1-3-6-4/h5H,1-3H2 | StdInChIKey = CNHYKKNIIGEXAY-UHFFFAOYSA-N | SMILES = C1CC(=N)SC1 | InChI1=1S/C4H7NS.ClH/c5-4-2-1-3-6-4;/h5H,1-3H2;1H | InChIKey1 = ATGUDZODTABURZ-UHFFFAOYSA-N | SMILES1 = C1CC(=N)SC1.Cl }} |Section2={{Chembox Properties | AtmosphericOHRateConstant = | Appearance = Powder | MeltingPtC = 198-201<ref name="Sigma">{{cite web | url = http://www.sigmaaldrich.com/catalog/product/sigma/i6256 | title = 2-Iminothiolane hydrochloride | publisher = Sigma-Aldrich}}</ref> | MeltingPt_notes = (HCl) | Density = | Formula = C<sub>4</sub>H<sub>7</sub>NS<br>C<sub>4</sub>H<sub>7</sub>NS·HCl | LogP = | MolarMass = 101.17 (free base)<br>137.63 (HCl)<ref name="Sigma"/> | pKa = | pKb = | Solubility = 100 mg/mL (HCl)<ref name="Sigma"/> | SolubleOther = | Solvent = | VaporPressure = }} }}
'''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.<ref>{{cite journal | pmid = 4581787| year = 1973| last1 = Traut| first1 = R. R.| title = Methyl 4-mercaptobutyrimidate as a cleavable cross-linking reagent and its application to the Escherichia coli 30S ribosome| journal = Biochemistry| volume = 12| issue = 17| pages = 3266–73| last2 = Bollen| first2 = A| last3 = Sun| first3 = T. T.| last4 = Hershey| first4 = J. W.| last5 = Sundberg| first5 = J| last6 = Pierce| first6 = L. R.| doi=10.1021/bi00741a019}}</ref>
It also reacts with aliphatic and phenolic hydroxyl groups at high pH, though at a much slower rate.<ref>{{Cite web|title = Traut's Reagent Instructions|url = https://tools.lifetechnologies.com/content/sfs/manuals/MAN0011238_Trauts_Reag_UG.pdf|website = Thermo Scientific|accessdate = 2015-07-08}}</ref> thumb|500x500px|The reaction of 2-iminothiolane with an amine group of a peptide.|centre
== References == <references/>
{{DEFAULTSORT:Iminothiolane, 2-}} Category:Thiolanes Category:Imino compounds