2-Iminothiolane

2-Iminothiolane Thiolan-2-imine Traut's reagent 2-Thiolanimine 120px|2-Iminothiolane 168px|2-Iminothiolane Hydrochloride Free base form Hydrochloride form (HCl) 6539-14-6 4781-83-3 10661959 10732937 DTXSID60524217 800-330-2 433941 13166855 5FP46MY9AM W688HZV733 1S/C4H7NS/c5-4-2-1-3-6-4/h5H,1-3H2 CNHYKKNIIGEXAY-UHFFFAOYSA-N C1CC(=N)SC1 1S/C4H7NS.ClH/c5-4-2-1-3-6-4;/h5H,1-3H2;1H ATGUDZODTABURZ-UHFFFAOYSA-N C1CC(=N)SC1.Cl Powder 198-201 http://www.sigmaaldrich.com/catalog/product/sigma/i6256 2-Iminothiolane hydrochloride Sigma-Aldrich (HCl) C4H7NSC4H7NS·HCl 101.17 (free base)137.63 (HCl) 100 mg/mL (HCl) 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. 4581787 1973 Traut R. R. Methyl 4-mercaptobutyrimidate as a cleavable cross-linking reagent and its application to the Escherichia coli 30S ribosome Biochemistry 12 17 3266–73 Bollen A Sun T. T. Hershey J. W. Sundberg J Pierce L. R. 10.1021/bi00741a019 It also reacts with aliphatic and phenolic hydroxyl groups at high pH, though at a much slower rate. Traut's Reagent Instructions https://tools.lifetechnologies.com/content/sfs/manuals/MAN0011238_Trauts_Reag_UG.pdf Thermo Scientific 2015-07-08 2015-07-09 https://web.archive.org/web/20150709060232/https://tools.lifetechnologies.com/content/sfs/manuals/MAN0011238_Trauts_Reag_UG.pdf dead thumb|500x500px|The reaction of 2-iminothiolane with an amine group of a peptide.|centre References Category:Thiolanes Category:Imino compounds