What is isothiocyanate?
What is isothiocyanate?
Isothiocyanates are naturally occurring small molecules that are formed from glucosinolate precursors of cruciferous vegetables. Many isothiocyanates, both natural and synthetic, display anticarcinogenic activity because they reduce activation of carcinogens and increase their detoxification.
What is the formula of isothiocyanate?
Ethyl isothiocyanate
| PubChem CID | 10966 |
|---|---|
| Structure | Find Similar Structures |
| Chemical Safety | Laboratory Chemical Safety Summary (LCSS) Datasheet |
| Molecular Formula | C3H5NS |
| Synonyms | Ethyl isothiocyanate 542-85-8 Isothiocyanatoethane Ethane, isothiocyanato- Ethyl mustard oil More… |
What does Phenylisothiocyanate react with?
Phenyl isocynate and phenyl isothiocyanate react with primary aromatic amines, with the formation of N,N′-disubstituted ureas. With amino acids they yield phenyl- or naphthylthio-hydantoins. This reaction is still used in Edman’s degradation of proteins, and estimation of their primary structure.
What are isothiocyanate glycosides?
1- A number of plants of the family Cruciferae yield glycosides containing sulphur. 2- Hydrolysis of these, yield volatile genins of thiocyanate structure e.g., mustard oils.
How do you make isothiocyanate?
Synthesis of isothiocyanates. A facile and general protocol for the preparation of isothiocyanates from alkyl and aryl amines relies on a tosyl chloride mediated decomposition of a dithiocarbamate salts that are generated in situ by treatment of amines with carbon disulfide and triethylamine.
What is the difference between thiocyanate and isothiocyanate?
The key difference between thiocyanate and isothiocyanate is that a thiocyanate is a functional group in which the alkyl or aryl group gets attached through the sulfur atom, whereas isothiocyanate is the linkage isomer of thiocyanate in which the alkyl or aryl group gets attached through the nitrogen atom.
Which of the following contains isothiocyanate glycosides?
Cruciferous vegetables, such as bok choi, broccoli, Brussels sprouts, cabbage, cauliflower, horseradish, kale, kohlrabi, mustard, radish, rutabaga, turnip, and watercress, are rich sources of glucosinolate precursors of isothiocyanates (63).
Why is Edman’s reaction important in protein chemistry?
It is able to accurately sequence up to 30 amino acids with modern machines capable of over 99% efficiency per amino acid. An advantage of the Edman degradation is that it only uses 10 – 100 pico-moles of peptide for the sequencing process.
What is allyl isothiocyanate used for?
It is used principally as a flavoring agent in foods. Synthetic allyl isothiocyanate is used as an insecticide, as an anti-mold agent bacteriocide, and nematicide, and is used in certain cases for crop protection. Hydrolysis of allyl isothiocyanate gives allylamine.
What does Edman’s reagent do?
Phenylisothiocyanate (PITC), also known as Edman’s Reagent, enables the sequential degradation of amino acids in a polypeptide chain, yielding primary structural information. PITC reacts readily with amino acids at alkaline pH. This method produces stable products with all amino acids, including proline.
What is Edman method of protein sequencing?
Edman degradation, developed by Pehr Edman, is a method of sequencing amino acids in a peptide. In this method, the amino-terminal residue is labeled and cleaved from the peptide without disrupting the peptide bonds between other amino acid residues.
How do isothiocyanates react with amino acids?
Isothiocyanates contain a very electrophilic carbon atom which can readily react with nucleophiles such as hydroxyl, amino, or thiol groups to form O -thiocarbamates, thioureas, or dithiocarbamates (see Fig. 1.13 ). The reaction with thiol groups is about 1000 times faster than with amine or hydroxyl groups [175].
What is the reaction of isothiocyanates with GSH?
Reaction of isothiocyanates with GSH. The reaction of isothiocyanate with thiols is a reversible reaction and the equilibrium shown in Fig. 6.2 is maintained. They also react with amino acids and amine groups to form other products (see Scheme 6.1). Sign in to download full-size image
How to prepare isothiocyanates from alkyl amines?
A facile and general protocol for the preparation of isothiocyanates from alkyl and aryl amines relies on a tosyl chloride mediated decomposition of a dithiocarbamate salts that are generated in situ by treatment of amines with carbon disulfide and triethylamine.
How are isothiocyanates detoxified in humans?
In aerobic organisms like humans, isothiocyanates are detoxified by conjugation with glutathione (GSH), which converts the electrophile to a dithiocarbamate in a conjugation reaction catalyzed by glutathione transferases (GSTs).
