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'''1-Aminocyclopropane-1-carboxylic acid''' ('''ACC''') is a disubstituted cyclic α-[[amino acid]] in which a three-membered [[cyclopropane]] ring is fused to the C{{sub|α}} atom of the amino acid.
'''1-Aminocyclopropane-1-carboxylic acid''' ('''ACC''') is a disubstituted cyclic α-[[amino acid]] in which a three-membered [[cyclopropane]] ring is fused to the C{{sub|α}} atom of the amino acid.


ACC plays an important role in the biosynthesis of the plant [[hormone]] [[ethylene]].<ref name="Yang_1984">{{cite journal |vauthors=Yang S, Hoffman N | title = Ethylene biosynthesis and its regulation in higher plants | journal = Annu. Rev. Plant Physiol. | volume = 35 | issue = | pages = 155–189 | year = 1984| doi = 10.1146/annurev.pp.35.060184.001103 }}</ref><ref name="Kende_1993">{{cite journal | author = Kende H | title = Ethylene biosynthesis | journal = Annu. Rev. Plant Physiol. | volume = 44 | issue = | pages = 283–307 | year = 1993| doi = 10.1146/annurev.pp.44.060193.001435 }}</ref> It is synthesized by the enzyme [[1-aminocyclopropane-1-carboxylate synthase|ACC synthase]] ( {{EC number|4.4.1.14}}) from [[methionine]] and converted to ethylene by [[Aminocyclopropanecarboxylate oxidase|ACC oxidase]] ({{EC number|1.14.17.4}}).<ref name="Kende_1989">{{cite journal | author = Kende H | title = Enzymes of Ethylene Biosynthesis | journal = Plant Physiol. | volume = 91 | issue = 1 | pages = 1–4 | year = 1989 | pmid = 16666977| doi = 10.1104/pp.91.1.1| url = http://www.plantphysiol.org/cgi/content/abstract/91/1/1 | pmc = 1061940 }}</ref>
ACC plays an important role in the biosynthesis of the plant [[hormone]] [[ethylene]].<ref name="Yang_1984">{{cite journal |vauthors=Yang S, Hoffman N | title = Ethylene biosynthesis and its regulation in higher plants | journal = Annu. Rev. Plant Physiol. | volume = 35 | issue = | pages = 155–189 | year = 1984| doi = 10.1146/annurev.pp.35.060184.001103 }}</ref><ref name="Kende_1993">{{cite journal | author = Kende H | title = Ethylene biosynthesis | journal = Annu. Rev. Plant Physiol. | volume = 44 | issue = | pages = 283–307 | year = 1993| doi = 10.1146/annurev.pp.44.060193.001435 }}</ref> It is synthesized by the enzyme [[1-aminocyclopropane-1-carboxylate synthase|ACC synthase]] ( {{EC number|4.4.1.14}}) from [[methionine]] and converted to ethylene by [[Aminocyclopropanecarboxylate oxidase|ACC oxidase]] ({{EC number|1.14.17.4}}).<ref name="Kende_1989">{{cite journal | author = Kende H | title = Enzymes of Ethylene Biosynthesis | journal = Plant Physiol. | volume = 91 | issue = 1 | pages = 1–4 | year = 1989 | pmid = 16666977| doi = 10.1104/pp.91.1.1| url = http://www.plantphysiol.org/cgi/content/abstract/91/1/1 | pmc = 1061940 }}</ref> ACC can be used by soil microorganisms (both bacteria and fungi) as a source of nitrogen and carbon<ref>{{Cite journal|last=Schenk|first=Peer M.|last2=Singh|first2=Brajesh|last3=Dennis|first3=Paul G.|last4=Crawford|first4=Mark|last5=Yan|first5=Lijuan|last6=Delgado-Baquerizo|first6=Manuel|last7=Carvalhais|first7=Lilia C.|last8=Khan|first8=Muhammad Yahya|last9=Liu|first9=Hongwei|date=2019-05-03|title=Soil amendments with ethylene precursor alleviate negative impacts of salinity on soil microbial properties and productivity|url=https://www.nature.com/articles/s41598-019-43305-4|journal=Scientific Reports|language=en|volume=9|issue=1|pages=1–13|doi=10.1038/s41598-019-43305-4|issn=2045-2322}}</ref>. 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<ref>{{Cite journal|last=Schenk|first=Peer M.|last2=Singh|first2=Brajesh|last3=Dennis|first3=Paul G.|last4=Crawford|first4=Mark|last5=Yan|first5=Lijuan|last6=Delgado-Baquerizo|first6=Manuel|last7=Carvalhais|first7=Lilia C.|last8=Khan|first8=Muhammad Yahya|last9=Liu|first9=Hongwei|date=2019-05-03|title=Soil amendments with ethylene precursor alleviate negative impacts of salinity on soil microbial properties and productivity|url=https://www.nature.com/articles/s41598-019-43305-4|journal=Scientific Reports|language=en|volume=9|issue=1|pages=1–13|doi=10.1038/s41598-019-43305-4|issn=2045-2322}}</ref>.


ACC is also an exogenous [[partial agonist]] of the mammalian [[NMDA receptor]].<ref name="pmid15996549">{{cite journal |vauthors=Inanobe A, Furukawa H, Gouaux E | title = Mechanism of partial agonist action at the NR1 subunit of NMDA receptors | journal = Neuron | volume = 47 | issue = 1 | pages = 71–84 | year = 2005 | pmid = 15996549 | doi = 10.1016/j.neuron.2005.05.022 }}</ref>
ACC is also an exogenous [[partial agonist]] of the mammalian [[NMDA receptor]].<ref name="pmid15996549">{{cite journal |vauthors=Inanobe A, Furukawa H, Gouaux E | title = Mechanism of partial agonist action at the NR1 subunit of NMDA receptors | journal = Neuron | volume = 47 | issue = 1 | pages = 71–84 | year = 2005 | pmid = 15996549 | doi = 10.1016/j.neuron.2005.05.022 }}</ref>

Revision as of 07:03, 13 August 2019

1-Aminocyclopropane-1-carboxylic acid
Names
Other names
1-Aminocyclopropanecarboxylic acid
Identifiers
3D model (JSmol)
Abbreviations ACC
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.108.227 Edit this at Wikidata
KEGG
  • InChI=1S/C4H7NO2/c5-4(1-2-4)3(6)7/h1-2,5H2,(H,6,7) checkY
    Key: PAJPWUMXBYXFCZ-UHFFFAOYSA-N checkY
  • InChI=1/C4H7NO2/c5-4(1-2-4)3(6)7/h1-2,5H2,(H,6,7)
    Key: PAJPWUMXBYXFCZ-UHFFFAOYAF
  • [1]: C(O)(=O)C1(CC1)(N)
  • O=C(O)C1(N)CC1
Properties
C4H7NO2
Molar mass 101.1 c
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

1-Aminocyclopropane-1-carboxylic acid (ACC) is a disubstituted cyclic α-amino acid in which a three-membered cyclopropane ring is fused to the Cα atom of the amino acid.

ACC plays an important role in the biosynthesis of the plant hormone ethylene.[2][3] It is synthesized by the enzyme ACC synthase ( EC 4.4.1.14) from methionine and converted to ethylene by ACC oxidase (EC 1.14.17.4).[4] ACC can be used by soil microorganisms (both bacteria and fungi) as a source of nitrogen and carbon[5]. 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[6].

ACC is also an exogenous partial agonist of the mammalian NMDA receptor.[7]

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[8].

References

  1. ^ 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 (2006). "MetaCyc: a multiorganism database of metabolic pathways and enzymes". Nucleic Acids Res. 34 (Database issue): D511–6. doi:10.1093/nar/gkj128. PMC 1347490. PMID 16381923.
  2. ^ Yang S, Hoffman N (1984). "Ethylene biosynthesis and its regulation in higher plants". Annu. Rev. Plant Physiol. 35: 155–189. doi:10.1146/annurev.pp.35.060184.001103.
  3. ^ Kende H (1993). "Ethylene biosynthesis". Annu. Rev. Plant Physiol. 44: 283–307. doi:10.1146/annurev.pp.44.060193.001435.
  4. ^ Kende H (1989). "Enzymes of Ethylene Biosynthesis". Plant Physiol. 91 (1): 1–4. doi:10.1104/pp.91.1.1. PMC 1061940. PMID 16666977.
  5. ^ Schenk, Peer M.; Singh, Brajesh; Dennis, Paul G.; Crawford, Mark; Yan, Lijuan; Delgado-Baquerizo, Manuel; Carvalhais, Lilia C.; Khan, Muhammad Yahya; Liu, Hongwei (2019-05-03). "Soil amendments with ethylene precursor alleviate negative impacts of salinity on soil microbial properties and productivity". Scientific Reports. 9 (1): 1–13. doi:10.1038/s41598-019-43305-4. ISSN 2045-2322.
  6. ^ Schenk, Peer M.; Singh, Brajesh; Dennis, Paul G.; Crawford, Mark; Yan, Lijuan; Delgado-Baquerizo, Manuel; Carvalhais, Lilia C.; Khan, Muhammad Yahya; Liu, Hongwei (2019-05-03). "Soil amendments with ethylene precursor alleviate negative impacts of salinity on soil microbial properties and productivity". Scientific Reports. 9 (1): 1–13. doi:10.1038/s41598-019-43305-4. ISSN 2045-2322.
  7. ^ Inanobe A, Furukawa H, Gouaux E (2005). "Mechanism of partial agonist action at the NR1 subunit of NMDA receptors". Neuron. 47 (1): 71–84. doi:10.1016/j.neuron.2005.05.022. PMID 15996549.
  8. ^ "Pesticide Experimental Use Permit; Receipt of Application; Comment Request" (PDF). Vol 84, Federal Register, No. 152: 38624. August 7, 2019 – via www.govinfo.gov.


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