207121-48-0

L-Cysteinesulfinic acid is an excitatory amino acid and agonist of metabotropic glutamate receptors (mGluRs). It increases intracellular inositol phosphate levels in CHO cells expressing mGluR1, mGluR5, or mGluR8 (EC₅₀s = 120, 30, and 110 μM, respectively) and inhibits forskolin-induced cAMP production in CHO cells expressing mGluR2 or mGluR6 and hamster kidney cells expressing mGluR4 (EC₅₀s = 100, 100, and 2,000 μM, respectively). It selectively binds to mGluR1α (K_i = 3,510 nM) over adrenergic, dopamine, histamine, muscarinic, nicotinic, or serotonin receptors (K_is = >10,000 nM for all). L-Cysteinesulfinic acid (1 mM) decreases mean arterial blood pressure and heart rate in rats when microinjected into the nucleus tractus solitarius (NTS). L-Cysteinesulfinic acid can be formed via oxidation of L-cysteine by reactive oxygen species (ROS), and conversion of cysteine to L-cysteinesulfinic acid in cysteine-containing peptide probes has been used to measure oxidative stress.

Off-White Solid

An amino acid derivative with neuropathological interest; Putative excitatory amino acid neurotransmitter.

reaction type: solution phase peptide synthesis

Cysteinesulfinic acid (CSA), also called 3-sulfinoalanine is synthesized by the conversion of sulfur to sulfinic acid in cysteine by the enzyme cysteine dioxygenase (CDO). CSA is a putative excitatory amino acid (EAA) with neurotransmitter functionality. It also regulates cardiovascular functions.

[1] TAKEMOTO Y. Cardiovascular actions of l-cysteine and l-cysteine sulfinic acid in the nucleus tractus solitarius of the rat[J]. Amino Acids, 2014, 46 7: 1707-1713. DOI: 10.1007/s00726-014-1733-z
[2] QI SHI. L-homocysteine sulfinic acid and other acidic homocysteine derivatives are potent and selective metabotropic glutamate receptor agonists.[J]. Journal of Pharmacology and Experimental Therapeutics, 2003, 305 1: 131-142. DOI: 10.1124/jpet.102.047092
[3] CHUN-LAN KENG. Design of Peptide-Based Probes for the Microscale Detection of Reactive Oxygen Species[J]. Analytical Chemistry, 2017, 89 20: 10883-10888. DOI: 10.1021/acs.analchem.7b02544