7634-96-0

Upstream product

• 50826-72-7 3-(acetylthio)-2-((acetylthio)methyl)propanoic acid 
• 10387-40-3 potassium thioacetate 
• 50891-94-6 β,β'-diiodoisobutyric acid 
• 859059-01-1 β,β'-bis-benzylsulfanyl-isobutyric acid methyl ester 

Downstream Products

• 2224-02-4 1,2-dithiolane-4-carboxylic acid 
• 79-31-2 isobutyric Acid 
• 952581-30-5 (3-thiolato-2-(thiolatomethyl)propanoic acid)(1,2-bis(diphenylphosphine)ethane)nickel(II) 

Relevant academic research and scientific papers

Synthesis of Asparagusic Acid Modified Lysine and its Application in Solid-Phase Synthesis of Peptides with Enhanced Cellular Uptake

Cyclic disulfides, such as asparagusic acid, enhance the uptake of a variety of cargoes into live cells. Here, we report a robust and scalable synthesis of an asparagusic acid modified lysine. This amino acid can be used in solid-phase peptide synthesis. We confirmed that incorporation of this building block into the sequence of a peptide increases its cellular uptake substantially.

Activation of disulfide bond cleavage triggered by hydrophobization and lipophilization of functionalized dihydroasparagusic acid

Concisely synthesized and functionalized dihydroasparagusic acid (DHAA) derivatives were used to show that the introduction of a hydrophobic functional group dramatically reduced air oxidation activity at the dithiol moieties and dominantly activated the cleavage of S-S bonds in proteins, presumably due to the hydrophobization and lipophilization. Notably, the reaction sites of water-reactive dithiol moieties behaved similarly to hydrophobic and lipophilic functional groups, which suggests impersonation of the reaction site.

Dihydroasparagusic acid: Antioxidant and tyrosinase inhibitory activities and improved synthesis

Dihydroasparagusic acid (DHAA) is the reduced form of asparagusic acid, a sulfur-containing flavor component produced by Asparagus plants. In this work, DHAA was synthetically produced by modifying some published protocols, and the synthesized molecule was tested in several in vitro assays (DPPH, ABTS, FRAP-ferrozine, BCB, deoxyribose assays) to evaluate its radical scavenging activity. Results show that DHAA is endowed with a significant in vitro antioxidant activity, comparable to that of Trolox. DHAA was also evaluated for its inhibitory activity toward tyrosinase, an enzyme involved, among others, in melanogenesis and in browning processes of plant-derived foods. DHAA was shown to exert an inhibitory effect on tyrosinase activity, and the inhibitor kinetics, analyzed by a Lineweaver-Burk plot, exhibited a competitive mechanism. Taken together, these results suggest that DHAA may be considered as a potentially active molecule for use in various fields of application, such as pharmaceutical, cosmetics, agronomic and food.

Properties of dihydroasparagusic acid and its use as an antidote against mercury(II) poisoning

Dihydroasparagusic acid is the first naturally occurring dimercaptanic compound that was isolated in 1948 from Asparagus concentrate. Although several synthetic procedures were proposed in the past decades for this natural substance, most of its chemical properties remain unstudied. In this work the capacity of the acid to act as an antidote against mercury(II) toxicity was evaluated in a simple biological model system, Saccharomyces cerevisiae, and is explained by the formation of a precipitate between mercury(II) and dihydroasparagusic acid. The precipitate was analyzed and studied. The solubility was determined by measuring in equilibrated solutions either the concentration of the total mercury(II) present in solution or the free concentration of hydrogen ions. The protonation constants were determined at 25 C and in 1.00 M NaCl, as constant ionic medium, by means of potential difference measurements of a galvanic cell with a glass electrode. The experimental data are explained by proposing the chemical composition of the precipitate and the value of its solubility product. As the solubility of the precipitate increases by increasing the concentration of dihydroasparagusic acid, the further formation of a complex between mercury(II) and dihydroasparagusic acid is assumed. Graphical abstract: [Figure not available: see fulltext.]

Composition to permanently reshape the hair containing at least one carboxydithiol

The present invention relates to an aqueous reducing composition, for the first step of a process to permanently reshape the hair, comprising, in a cosmetically acceptable medium, one or more carboxydithiols as reducing agents.

Comparisons of rate constants for thiolate-disulfide interchange in water and in polar aprotic solvents using dynamic 1H NMR line shape analysis

The rate constants for representative thiolate-disulfide interchange reactions are larger in DMSO and DMF than in water by a factor of approximately 2300 at 24 °C. The log of the rate constant is directly proportional to the mole fraction of D2O in mixtures of DMSO and D2O, even at small mole fractions of D2O. This linear proportionality suggests that thiolate anion is not specifically solvated by water and that hydrogen bonding is relatively unimportant in stabilizing this species. The values of ΔS# for thiolate-disulfide interchange are approximately -10 cal/(deg mol), presumptively because of loss in the entropy of the reactants in going from ground to transition state, partially compensated by a gain in entropy from solvent release. Introduction of a hydroxyl group β to the C-S bond slows the reaction by a factor of 2-15; the introduction of methyl groups β to the C-S bond slows the rate by factors of 3-20. A number of substances have been screened as potential catalysts for thiolate-disulfide interchange in water: none showed useful levels of catalytic activity, although phenylselenol did accelerate the interchange significantly.

Biosynthesis of Sulfur Compounds. Investigations of the Biosinthesis of Asparagusic Acid.

Investigations of the biosynthesis of the naturally occuring 1,2-dithiolane asparagusic acid (1) in Asparagus officinalis have shovn that the substance is derived from inobutyric acid via the intermediacy of methacrylic acid, 2-methyl-3-mercaptopropionic acid, and S-(2-carboxy-n-propyl) cysteine.The conversion of isobutyric acid to methacrylic acid in Asparagus has also been shown to proceed by oxidation of the 2-pro-S methyl group of isobutyrate.Finally, the absolute configuration of naturally occuring S-(2-carboxy-n-propyl)cysteine has been determined.