351422-29-2

Usage

Uses

Used in Chemical Synthesis:
(R)-2-Amino-2-carboxyethylmethanethiosulfonate is used as a building block in chemical synthesis for the creation of various organic compounds and pharmaceuticals. Its amine and carboxylic acid groups facilitate the formation of amide bonds, making it a valuable component in the synthesis of peptides, proteins, and other bioactive molecules.
Used in Analytical Chemistry:
In analytical chemistry, (R)-2-Amino-2-carboxyethylmethanethiosulfonate serves as a reagent for the detection and quantification of various substances. Its functional groups can be exploited to develop assays and sensors, enhancing the sensitivity and specificity of analytical methods.
Used in Material Science:
(R)-2-Amino-2-carboxyethylmethanethiosulfonate is used as a functionalizing agent in material science, particularly for the modification of surfaces and the development of new materials with tailored properties. Its amine and carboxylic acid groups can be used to attach the compound to various substrates, enabling the creation of self-assembled monolayers and other functional coatings.
Used in Environmental Applications:
In environmental applications, (R)-2-Amino-2-carboxyethylmethanethiosulfonate can be employed as a chelating agent to remove heavy metals from contaminated water or soil. Its ability to form stable complexes with metal ions makes it a promising candidate for environmental remediation efforts.
Used in Biomedical Research:
(R)-2-Amino-2-carboxyethylmethanethiosulfonate is used as a research tool in biomedical studies, where it can be employed to modify biomolecules or to investigate the interactions between different cellular components. Its functional groups allow for the covalent attachment of the compound to proteins, nucleic acids, or other biomolecules, facilitating the study of their structure and function.

InChI:InChI=1/C4H9NO4S2/c1-11(8,9)10-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/t3-/m0/s1

Upstream product

• 52-89-1 l-cysteine hydrochloride 
• 20277-69-4 sodium methansulfinate 

Relevant academic research and scientific papers

Convenient synthesis of multifunctional EDTA-based chiral metal chelates substituted with an S-mesylcysteine

We describe the synthetic route to ethylenediaminetetraacetic acid (EDTA) derivatives that can be attached to surface-exposed thiol functional groups of cysteine residues in proteins, via a methylthiosulfonate moiety that is connected in a stereochemically unique way to the C-1 carbon atom of EDTA. Such compounds can be used to align proteins in solution without the need to add liquid crystalline media, and are, therefore, of great interest for the NMR spectroscopic analysis of biomolecules. The binding constant for the paramagnetic tag to lanthanide ions was determined by measuring luminescence. For the Tb+3-ligand complex, a Kb value of 6.5×1017-1 was obtained. This value is in excellent agreement with literature values for the related EDTA compound. In addition, it could be shown that there is no significant reduction in the luminescence intensity upon addition of a 104 excess of Ca2+ ions, indicating that this paramagnetic tag is compatible with buffers containing high concentrations of divalent alkaline earth ions.

Diazotization of S-Sulfonyl-cysteines

We report the preparation of enantiomerically enriched β-thio-α-hydroxy and α-chloro carboxylic acid and ester building blocks by diazotization of S-sulfonyl-cysteines. The thiosulfonate protecting group demonstrated resistance to oxidation and attenuation of sulfur's nucleophilicity by the anomeric effect. The key transformation was optimized by a 22 factorial design of experiment, highlighting the unique reactivity of cysteine derivatives in comparison with aliphatic amino acids.