1-Aminocyclopropane-1-carboxylic acid
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1-Aminocyclopropane-1-carboxylic acid (ACC) is a disubstituted cyclic α-
amino acid Amino acids are organic compounds that contain both amino and carboxylic acid functional groups. Although hundreds of amino acids exist in nature, by far the most important are the alpha-amino acids, which comprise proteins. Only 22 alpha a ...
in which a cyclopropane ring is fused to the C atom of the amino acid. It is a white solid. Many cyclopropane-substituted amino acids are known, but this one occurs naturally. Like glycine, but unlike most α-amino acids, ACC is not chiral.


Biochemistry

ACC is the precursor to the plant hormone ethylene. It is synthesized by the enzyme ACC synthase () from methionine and converted to ethylene by ACC oxidase (). ACC also exhibits ethylene-independent signaling that plays a critical role in
pollination Pollination is the transfer of pollen from an anther of a plant to the stigma of a plant, later enabling fertilisation and the production of seeds, most often by an animal or by wind. Pollinating agents can be animals such as insects, birds, a ...
and seed production by activating proteins similar to those involved in nervous system responses in humans and animals. More specifically, ACC signaling promotes secretion of the pollen tube chemoattractant LURE1.2 in ovular sporophytic tissue thus enhancing pollen tube attraction. Additionally, ACC activates Ca2+-containing ion currents via glutamate receptor-like (GLR) channels in root protoplasts. ACC can be used by soil microorganisms (both
bacteria Bacteria (; singular: bacterium) are ubiquitous, mostly free-living organisms often consisting of one Cell (biology), biological cell. They constitute a large domain (biology), domain of prokaryotic microorganisms. Typically a few micrometr ...
and
fungi A fungus ( : fungi or funguses) is any member of the group of eukaryotic organisms that includes microorganisms such as yeasts and molds, as well as the more familiar mushrooms. These organisms are classified as a kingdom, separately from ...
) as a source of
nitrogen Nitrogen is the chemical element with the symbol N and atomic number 7. Nitrogen is a nonmetal and the lightest member of group 15 of the periodic table, often called the pnictogens. It is a common element in the universe, estimated at se ...
and
carbon Carbon () is a chemical element with the symbol C and atomic number 6. It is nonmetallic and tetravalent—its atom making four electrons available to form covalent chemical bonds. It belongs to group 14 of the periodic table. Carbon mak ...
. As such, using ACC to incubate soils has been proven to induce the gene abundance encoding ACC- deaminases, which may have positive consequences on
plant growth Important structures in plant development are buds, shoots, roots, leaves, and flowers; plants produce these tissues and structures throughout their life from meristems located at the tips of organs, or between mature tissues. Thus, a living plant a ...
and stress tolerance. ACC has also been extracted from
kelp Kelps are large brown algae seaweeds that make up the order Laminariales. There are about 30 different genera. Despite its appearance, kelp is not a plant - it is a heterokont, a completely unrelated group of organisms. Kelp grows in "underwa ...
. ACC is also an exogenous partial agonist of the mammalian NMDA receptor. In 2019, the
United States Environmental Protection Agency The Environmental Protection Agency (EPA) is an independent executive agency of the United States federal government tasked with environmental protection matters. President Richard Nixon proposed the establishment of EPA on July 9, 1970; it ...
issued notice of an application for an experimental use permit to be issued for use of ACC as a pesticide.


References

Cyclic amino acids Cyclopropanes NMDA receptor agonists {{nervous-system-drug-stub