Description
1-
Aminocyclopropanecarboxylic acid (ACPC) is an intermediate in the synthesis of ethylene, the plant hormone responsible for biological processes ranging from seed germination to organ senescence. ACPC has been shown to modulate NMDA receptor activity by acting as a partial agonist at the glycine-
binding site on NMDA receptors (EC
50 = 0.7-
0.9 μM) in the presence of low levels (1 μM) of glutamate and as a competitive antagonist at the glutamate-
binding site on NMDA receptors (EC
50 = 81.6 nM) with high levels (10 μM) of glutamate. This compound has been reported to protect against neuron cell death in
in vivo models of ischemia by enabling moderate levels of NMDA receptor activation and attenuating any excess NMDA receptor signaling that may lead to neurotoxicity.
Chemical Properties
Crystalline
Uses
1-Aminocyclopropane-1-carboxylic Acid is an intermediate in the conversion of methionine to ethylene during the ripening in apples. It also plays an important role in the biosynthesis of the plant hormone ethylene.1-Aminocyclopropane-1-carboxylic Acid is shown to block convulsions and death produced by NMDA exposure, significantly reducing seizure induction and cell death of NMDA-treated hippocampal neurons. 1-Aminocyclopropane-1-carboxylic Acid is produced endogenously in the tomato and other higher plants as a product of the action of 1-aminocyclopropane-1-carboxylic acid synthase in the biosynthesis of ethylene.
Uses
1-Aminocyclopropane-1-carboxylic Acid is a plant growth regulator. It is an NMDA agonist acting at the glycine site.
Definition
ChEBI: 1-aminocyclopropanecarboxylic acid is a non-proteinogenic alpha-amino acid consisting of cyclopropane having amino and carboxy substituents both at the 1-position. It has a role as a plant metabolite and a member of ethylene releasers. It is a monocarboxylic acid and a non-proteinogenic alpha-amino acid. It is functionally related to a cyclopropanecarboxylic acid. It is a conjugate acid of a 1-aminocyclopropanecarboxylate. It is a tautomer of a 1-aminocyclopropanecarboxylic acid zwitterion.
Application
1-aminocyclopropanecarboxylic acid (ACC) is used in the following ways:
(1) Organic synthesis. It is used for the preparation of vinyls and for the formation of imine compounds by decarboxylation with triketones.
(2) Used as a substrate for the determination of ACC deaminase activity for the study of the growth-promoting effects of endophytic isolates obtained from fern roots and cucurbit seeds.
(3) Used as an ethylene precursor to study the effect of high ethylene concentration on lateral root density (LRD) in sorghum brown midrib (bmr) mutants.
(4) Used to study the effect of glycine on the antidepressant and anxiolytic effects of ACC in rats.
Production Methods
ACC is produced through an industrial process that typically begins with preparation of a suitably protected amino-acid precursor, followed by a controlled cyclopropanation step that forms the strained three-membered ring while suppressing rearrangements and over-alkylation. Once the cyclopropane framework is established, deprotection and purification steps yield the free amino acid, with downstream operations centred on crystallisation, solvent removal, and multi-stage filtration to meet agrochemical specifications for optical purity, residual solvents, and trace by-products.
General Description
1-Aminocyclopropanecarboxylic acid is a member of 1-aminocycloalkanecarboxylic acids.
Biochem/physiol Actions
1-Aminocyclopropanecarboxylic acid (ACC) exhibits anticonvulsant, anxiolytic, anti-addictive, neuroprotective and antidepressant-like effects in rats and mice. ACC does not affect memory or learning processes.
Mechanism of action
As an ethylene releasing substance it affects the growth and development of plants as well as their senescence.
References
[1] A B BLEECKER H K. Ethylene: a gaseous signal molecule in plants.[J]. Annual review of cell and developmental biology, 2000, 16: 1-18. DOI:
10.1146/annurev.cellbio.16.1.1[2] R NAHUM-LEVY. Putative partial agonist 1-aminocyclopropanecarboxylic acid acts concurrently as a glycine-site agonist and a glutamate-site antagonist at N-methyl-D-aspartate receptors.[J]. Molecular Pharmacology, 1999, 56 6: 1207-1218. DOI:
10.1124/mol.56.6.1207
Pesticide Type
Herbicide; Plant Growth Regulator
