1-Aminocyclopropane-1-carboxylic acid

changed changed 477187415 1-aminocyclopropanecarboxylic acid 200.svg ACC-3D-balls.png ACC-3D-spacefill.png ACC-zwitterion-3D-spacefill.png ACC-zwitterion-3D-balls.png 128px 1-Aminocyclopropane-1-carboxylic acid 1-Aminocyclopropane-1-carboxylic acid 1-Aminocyclopropanecarboxylic acid ACC correct chemspider correct EBI 58360 520 correct kegg C01234 1/C4H7NO2/c5-4(1-2-4)3(6)7/h1-2,5H2,(H,6,7) PAJPWUMXBYXFCZ-UHFFFAOYAF O=C(O)C1(N)CC1 correct EBI 265325 correct chemspider 1S/C4H7NO2/c5-4(1-2-4)3(6)7/h1-2,5H2,(H,6,7) correct chemspider PAJPWUMXBYXFCZ-UHFFFAOYSA-N correct CAS 22059-21-8 correct FDA 3K9EJ633GL 535 correct drugbank DB02085 C(O)(=O)C1(CC1)(N) Caspi R, Foerster H, Fulcher CA, Hopkinson R, Ingraham J, Kaipa P, Krummenacker M, Paley S, Pick J, Rhee SY, Tissier C, Zhang P, Karp PD 6 MetaCyc: a multiorganism database of metabolic pathways and enzymes Nucleic Acids Research 34 Database issue D511-6 January 2006 16381923 1347490 10.1093/nar/gkj128 4 7 1 2 101.1 2 c 198-201 1-Aminocyclopropane-1-carboxylic acid (ACC) is a disubstituted cyclic α-amino acid in which a cyclopropane ring is fused to the Cα atom of the amino acid. It is a white solid. Many cyclopropane-substituted amino acids are known, but this one occurs naturally in various fruits.Brackmann F, de Meijere A Natural Occurrence, Syntheses, and Applications of Cyclopropyl-Group-Containing α-Amino Acids. 1. 1-Aminocyclopropanecarboxylic Acid and Other 2,3-Methanoamino Acids Chemical Reviews 107 11 4493–4537 November 2007 10.1021/cr078376j 17944521 Like glycine, but unlike most α-amino acids, ACC is not chiral. Biochemistry ACC is the precursor to the plant hormone ethylene.Yang S, Hoffman N Ethylene biosynthesis and its regulation in higher plants Annu. Rev. Plant Physiol. 35 155–189 1984 10.1146/annurev.pp.35.060184.001103 Kende H Ethylene biosynthesis Annu. Rev. Plant Physiol. 44 283–307 1993 10.1146/annurev.pp.44.060193.001435 It is synthesized by the enzyme ACC synthase (4.4.1.14) from methionine and converted to ethylene by ACC oxidase (1.14.17.4). Kende H Enzymes of ethylene biosynthesis Plant Physiology 91 1 1–4 September 1989 16666977 1061940 10.1104/pp.91.1.1 ACC also exhibits ethylene-independent signaling that plays a critical role in pollination 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. Mou W, Kao YT, Michard E, Simon AA, Li D, Wudick MM, Lizzio MA, Feijó JA, Chang C 6 Ethylene-independent signaling by the ethylene precursor ACC in Arabidopsis ovular pollen tube attraction Nature Communications 11 1 4082 August 2020 32796832 7429864 10.1038/s41467-020-17819-9 2020NatCo..11.4082M free ACC can be used by soil microorganisms (both bacteria and fungi) as a source of nitrogen and carbon. Liu H, Khan MY, Carvalhais LC, Delgado-Baquerizo M, Yan L, Crawford M, Dennis PG, Singh B, Schenk PM 6 Soil amendments with ethylene precursor alleviate negative impacts of salinity on soil microbial properties and productivity Scientific Reports 9 1 6892 May 2019 31053834 6499801 10.1038/s41598-019-43305-4 free 2019NatSR...9.6892L 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 and stress tolerance. Farahat MG, Mahmoud MK, Youseif SH, Saleh SA, Kamel Z 2020 Alleviation of salinity stress in wheat by ACC deaminase-producing Bacillus aryabhattai EWR29 with multifarious plant growth-promoting attributes https://scholar.cu.edu.eg/?q=farahat/publications/alleviation-salinity-stress-wheat-acc-deaminase-producing-bacillus-aryabhattai- Plant Archives 20 1 417–429 ACC has also been extracted from kelp. Nelson W, van Staden J Aminocyclopropane-1-carboxylic acid in seaweed concentrate Botanica Marina 28 9 1985 415-417 10.1515/botm.1985.28.9.415 ACC is also an exogenous partial agonist of the mammalian NMDA receptor. Inanobe A, Furukawa H, Gouaux E Mechanism of partial agonist action at the NR1 subunit of NMDA receptors Neuron 47 1 71–84 July 2005 15996549 10.1016/j.neuron.2005.05.022 16033761 free In 2019, the United States Environmental Protection Agency issued notice of an application for an experimental use permit to be issued for use of ACC as a pesticide.August 7, 2019 Pesticide Experimental Use Permit; Receipt of Application; Comment Request https://www.govinfo.gov/content/pkg/FR-2019-08-07/pdf/2019-16810.pdf Federal Register 84 152 38624 www.govinfo.gov References 2 Category:Alpha-amino acids Category:Cyclic amino acids Category:Cyclopropanes Category:NMDA receptor agonists