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Traut's Reagent (2-Iminothiolane•HCl)


Modifies primary amines to sulfhydryl groups for immediate use.

Pierce Traut's Reagent (2-iminothiolane)

Thermo Scientific Pierce Traut's Reagent (2-iminothiolane) is a small thiolation compound that reacts with primary amines (e.g., lysine side chains) to add a small spacer arm (8.1 angstroms) terminated by a free sulfhydryl group.

Traut's Reagent (2-iminothiolane or 2-IT) is a cyclic thioimidate compound for thiolation (sulfhydryl addition). Traut's Reagent reacts with primary amines (–NH2) to introduce sulfhydryl (–SH) groups while maintaining charge properties similar to the original amino group. Once added, sulfhydryl groups can be specifically targeted for reaction in a variety of useful labeling, crosslinking and immobilization procedures.

Highlights:

  • Simple – one-step conversion of amines to sulfhydryls
  • Specific – selective and spontaneous modification of primary amines at pH 7-10
  • Flexible – incorporates a five-atom spacer arm to reduce steric hindrance
  • Soluble – preserves the original positive charge to preserve protein solubility

Product Details:

2-iminothiolane; Traut's Reagent

Structure and properties of Traut's Reagent:

  • Alternative names: 2-Iminothiolane, 2-IT
  • Molecular formula: C3H7NS•HCl
  • Molecular weight: 137.63
  • CAS number: 4781-83-3
  • Absorption maximum: 248nm (in 0.1M HCl)
  • Extinction coefficient: 8840 M-1 cm-1 (in 0.1M HCl)
  • Solubility: water or aqueous buffer
  • Storage conditions: store at 4°C with desiccant

 

Reaction scheme for 2-Iminothiolane (2-IT) with proteins and peptides.
Reaction scheme of Traut's Reagent (2-iminothiolane). The target may be a protein, peptide or other primary amine-containing molecule.

References:

  1. Traut, R.R., et al. (1973). Methyl 4-mercaptobutyrimidate as a cleavable cross-linking reagent and its application to the Escherichia coli 30S ribosome. Biochem 12(17):3266-73.
  2. Jue, R., et al. (1978). Addition of sulfhydryl groups to Escherichia coli ribosomes by protein modification with 2-iminothiolane (methyl 4- mercaptobutyrimidate). Biochem 17(25):5399-5405.
  3. D'Oro, U., et al. (2002). Regulation of constitutive TCR internalization by the zeta-chain. J Immunol 169:6269-78.
  4. Newton, D.L., et al. (2001). Potent and specific antitumor effects of an anti-CD22-targeted cytotoxic ribonuclease: potential for the treatment of non-Hodgkin lymphoma. Blood 97:528-35.
  5. Stanisic, D.I., et al. (2003). Analysis of immunological nonresponsiveness to the 19-kilodalton fragment of merozoite surface protein 1 of Plasmodium yoelii. Infec Immunity 71(10):5700-13.

Related Resources:

Overview of crosslinking and protein modification

Related Products:

SATA – alternative sulfhydryl-addition reagent
SATP – slightly longer version of SATA
SAT(PEG)4 – alternative sulfhydryl-addition reagent with long, PEG spacer arm
Hydroxylamine – deprotects sulfhydryls after SATA modification
SPDP – amine-to-sulfhydryl crosslinker


Ordering Information
 
Product # Description Pkg. Size Instructions MSDS CofA Price
26101 Traut's Reagent
Formulation: 2-Iminothiolane hydrochloride; powder solid
Sufficient For: 3633mL of typical 1X (1mM) reaction solution, or approx. 250 uses at 2mg reagent per use
500mg Product Instructions for product #26101 Traut's Reagent MSDS for product #26101 Traut's Reagent Certificate of Analysis for product #26101 Traut's Reagent $136.00

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Instructions | MSDS | CofA
Product Instructions | MSDS | CofA  

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