3-Mercaptopropionic acid (3-MPA) is an
organosulfur compound
Organosulfur compounds are organic compounds that contain sulfur. They are often associated with foul odors, but many of the sweetest compounds known are organosulfur derivatives, e.g., saccharin. Nature abounds with organosulfur compounds—sulf ...
with the formula HSCH
2CH
2CO
2H. It is a
bifunctional
In organic chemistry, when a single organic molecule has two different functional groups, it is called a bifunctional molecule . A bifunctional molecule has the properties of two different types of functional groups, such as an alcohol (), amide ( ...
molecule, containing both carboxylic acid and thiol groups. It is a colorless oil. It is derived from the addition of hydrogen sulfide to
acrylic acid
Acrylic acid (IUPAC: propenoic acid) is an organic compound with the formula CH2=CHCOOH. It is the simplest unsaturated carboxylic acid, consisting of a vinyl group connected directly to a carboxylic acid terminus. This colorless liquid has a ch ...
.
Reactions and uses
It is competitive inhibitor of
glutamate decarboxylase, and therefore acts as a
convulsant A convulsant is a drug which induces convulsions and/or epileptic seizures, the opposite of an anticonvulsant. These drugs generally act as stimulants at low doses, but are not used for this purpose due to the risk of convulsions and consequent exci ...
. It has higher
potency and faster
onset of action compared to
allylglycine
Allylglycine is a glycine derivative. It is an inhibitor of glutamate decarboxylase. Inhibition of glutamate decarboxylase blocks GABA biosynthesis, leading to lower levels of the neurotransmitter. Allylglycine is known to induce seizures in an ...
.
It is used to prepare hydrophilic
gold nanoparticles, exploiting the affinity of gold for sulfur ligands.
See also
*
Allylglycine
Allylglycine is a glycine derivative. It is an inhibitor of glutamate decarboxylase. Inhibition of glutamate decarboxylase blocks GABA biosynthesis, leading to lower levels of the neurotransmitter. Allylglycine is known to induce seizures in an ...
*
Thiolactic acid
Thiolactic acid is the organosulfur compound with the formula HSCH2CO2H. The molecule contains both carboxylic acid and thiol functional groups. It is structurally related to lactic acid by the interchange of SH for OH. It is a colorless oil.
T ...
(2-mercaptopropionic acid)
References
Convulsants
Glutamate decarboxylase inhibitors
Thiols
Propionic acids
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