2-iminothiolane

Structural formula
	left the free base, right the hydrochloride
General
Surname	2-iminothiolane
other names	Trauts reagent; Methyl 4-mercaptobutyrimidate hydrochloride; Tetrahydrothiophene-2-imine;
Molecular formula	C 4 H 7 NS • HCl
Brief description	white crystalline solid (hydrochloride)
External identifiers / databases
EC number	800-330-2
ECHA InfoCard	100.226.745
PubChem	13166855
ChemSpider	10732937
Wikidata	Q209411
properties
Molar mass	137.63 g mol −1 (hydrochloride); 101.17 g mol −1 (free base);
Physical state	firmly
density	1.28 g · cm³
Melting point	198–201 ° C (hydrochloride)
boiling point	142.6 ° C (free base)
solubility	Easily soluble as the hydrochloride in water (100 g / l) and methanol
safety instructions
GHS labeling of hazardous substances Hydrochloride	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

2-Iminothiolane , also known as Traut's reagent , is a cyclic thioimidate . The compound is mainly used for the thiolation of primary amines in biochemistry .

application

2-Iminothiolane reacts with primary amines, for example with the N-terminus of a peptide or within a peptide with the ε- amino group of lysine , with ring opening and formation of a thiol . The reaction is usually carried out in a buffered aqueous solution with a pH of 7 to 10 and at room temperature.

In subsequent steps, functional molecular groups can be coupled to the thiol, for example via a maleimide linker or via a disulfide bridge bond . 2-iminothiolane was first in 1973 by R. Robert Trautmann and colleagues at the University of California ( Department of Biological Chemistry of the School of Medicine ) for the thiolation of the 30S subunit of the ribosome of Escherichia coli used. This is why 2-iminothiolane is also known as Traut's reagent .

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

The length of the linker for a protein-protein coupling is 1.45 nm, for an RNA-protein coupling it is 0.5 nm.

properties

The octanol-water partition coefficient (log P) is 0.74. 2-Iminothiolane is usually stored at 2 to 8 ° C

literature

MJ McCall et al .: Simplified method for conjugating macrocyclic bifunctional chelating agents to antibodies via 2-iminothiolane. In: Bioconjug Chem 1, 1990, pp. 222-226, PMID 2096914 .
GL DeNardo et al .: Comparison of 1,4,7,10-tetraazacyclododecane-N, N ′, N ′ ′, N ′ ′ ′ - tetraacetic acid (DOTA) -peptide-ChL6, a novel immunoconjugate with catabolizable linker, to 2- iminothiolane-2- [p- (bromoacetamido) benzyl] -DOTA-ChL6 in breast cancer xenografts. In: Clin Cancer Res 4, 1998, pp. 2483-2490, PMID 9796981 .
GL DeNardo et al .: Preclinical evaluation of cathepsin-degradable peptide linkers for radioimmunoconjugates. In: Clin Cancer Res 9, 2003, pp. 3865S-3872S, PMID 14506184 .
F. Hahn et al .: 2-Iminothiolane as a Useful Coupling Reagent for Polyamine Solid-Phase Synthesis. In: Synlett 2008, pp. 2785-2790. doi: 10.1055 / s-0028-1083566
R. Jue et al .: Addition of sulfhydryl groups to Escherichia coli ribosomes by protein modification with 2-iminothiolane (methyl 4-mercaptobutyrimidate). In: Biochemistry 17, 1978, pp. 5399-5406, PMID 365229 .

Dissertations

F. Lewrick: Active liposomal targeting of endocrine tumors. (PDF; 1.7 MB) Dissertation, University of Freiburg im Breisgau, 2008, p. 56.
M. Gantert: Glucose oxidase liposomes for the therapy of septic granulomatosis: Active drug targeting with liposomally coupled IgG antibodies. (PDF; 9.3 MB) Dissertation, University of Freiburg im Breisgau, 2007, p. 70.

Individual evidence

↑ ^a ^b ^c ^d ^e data sheet 2-Iminothiolane hydrochloride from Sigma-Aldrich , accessed on May 12, 2011 ( PDF ).
↑ ^a ^b Entry on 2-iminotetrahydrothiophenes in the ChemSpider database of the Royal Society of Chemistry , accessed on January 22, 2014.
↑ Data sheet 2-Iminothiolane, Hydrochloride from Santa Cruz Biotechnology, Inc., accessed December 29, 2011.
↑ RR Traut et al.: Methyl 4-mercaptobutyrimidate as a cleavable cross-linking reagent and its application to the Escherichia coli 30S ribosome. In: Biochemistry 12, 1973, pp. 3266-3273, PMID 4581787 .
↑ R. Jue, JM Lambert, LR Pierce, RR Traut: Addition of sulfhydryl groups to Escherichia coli ribosomes by protein modification with 2-iminothiolane (methyl 4-mercaptobutyrimidate). In: Biochemistry Volume 17, Number 25, December 1978, pp. 5399-5406, ISSN 0006-2960 . PMID 365229 .
↑ Max Planck Institute for Molecular Genetics: 2-iminothiolane ( Memento from February 1, 2010 in the Internet Archive ) accessed on October 21, 2009.
↑ ChemDB: tetrahydrothiophen-2-imine accessed on October 21, 2009.

[Sigma-1] ↑ ^a ^b ^c ^d ^e data sheet 2-Iminothiolane hydrochloride from Sigma-Aldrich , accessed on May 12, 2011 ( PDF ).

[spider-2] Entry on 2-iminotetrahydrothiophenes in the ChemSpider database of the Royal Society of Chemistry , accessed on January 22, 2014.

[3] Data sheet 2-Iminothiolane, Hydrochloride from Santa Cruz Biotechnology, Inc., accessed December 29, 2011.

[4] RR Traut et al.: Methyl 4-mercaptobutyrimidate as a cleavable cross-linking reagent and its application to the Escherichia coli 30S ribosome. In: Biochemistry 12, 1973, pp. 3266-3273, PMID 4581787 .

[5] R. Jue, JM Lambert, LR Pierce, RR Traut: Addition of sulfhydryl groups to Escherichia coli ribosomes by protein modification with 2-iminothiolane (methyl 4-mercaptobutyrimidate). In: Biochemistry Volume 17, Number 25, December 1978, pp. 5399-5406, ISSN 0006-2960 . PMID 365229 .

[6] Max Planck Institute for Molecular Genetics: 2-iminothiolane ( Memento from February 1, 2010 in the Internet Archive ) accessed on October 21, 2009.

[chemDB-7] ChemDB: tetrahydrothiophen-2-imine accessed on October 21, 2009.