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1-Aminocyclopropane-1-carboxylic acid

March 14, 2024

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.[2][verification needed] Like glycine, but unlike most α-amino acids, ACC is not chiral.

1-Aminocyclopropane-1-carboxylic acid
Names
Preferred IUPAC name
1-Aminocyclopropane-1-carboxylic acid
Other names
1-Aminocyclopropanecarboxylic acid
Identifiers
  • 22059-21-8 Y
3D model (JSmol)
  • [1]: Interactive image
  • Interactive image
Abbreviations ACC
ChEBI
  • CHEBI:58360 Y
ChEMBL
  • ChEMBL265325 Y
ChemSpider
  • 520 Y
DrugBank
  • DB02085 Y
ECHA InfoCard 100.108.227
KEGG
  • C01234 Y
  • 535
UNII
  • 3K9EJ633GL Y
  • DTXSID9039577
  • InChI=1S/C4H7NO2/c5-4(1-2-4)3(6)7/h1-2,5H2,(H,6,7) Y
    Key: PAJPWUMXBYXFCZ-UHFFFAOYSA-N Y
  • 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
Melting point 198–201 °C (388–394 °F; 471–474 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)

Biochemistry edit

ACC is the precursor to the plant hormone ethylene.[3][4] 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).[5]

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.[6]

ACC can be used by soil microorganisms (both bacteria and fungi) as a source of nitrogen and carbon.[7] 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.[7][8]

ACC has also been extracted from kelp.[9]

ACC is also an exogenous partial agonist of the mammalian NMDA receptor.[10]

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.[11]

References edit

  1. ^ Caspi R, Foerster H, Fulcher CA, Hopkinson R, Ingraham J, Kaipa P, et al. (January 2006). "MetaCyc: a multiorganism database of metabolic pathways and enzymes". Nucleic Acids Research. 34 (Database issue): D511-6. doi:10.1093/nar/gkj128. PMC 1347490. PMID 16381923.
  2. ^ Brackmann F, de Meijere A (November 2007). "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. doi:10.1021/cr078376j. PMID 17944521.
  3. ^ 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.
  4. ^ Kende H (1993). "Ethylene biosynthesis". Annu. Rev. Plant Physiol. 44: 283–307. doi:10.1146/annurev.pp.44.060193.001435.
  5. ^ Kende H (September 1989). "Enzymes of ethylene biosynthesis". Plant Physiology. 91 (1): 1–4. doi:10.1104/pp.91.1.1. PMC 1061940. PMID 16666977.
  6. ^ Mou W, Kao YT, Michard E, Simon AA, Li D, Wudick MM, et al. (August 2020). "Ethylene-independent signaling by the ethylene precursor ACC in Arabidopsis ovular pollen tube attraction". Nature Communications. 11 (1): 4082. Bibcode:2020NatCo..11.4082M. doi:10.1038/s41467-020-17819-9. PMC 7429864. PMID 32796832.
  7. ^ a b Liu H, Khan MY, Carvalhais LC, Delgado-Baquerizo M, Yan L, Crawford M, et al. (May 2019). "Soil amendments with ethylene precursor alleviate negative impacts of salinity on soil microbial properties and productivity". Scientific Reports. 9 (1): 6892. Bibcode:2019NatSR...9.6892L. doi:10.1038/s41598-019-43305-4. PMC 6499801. PMID 31053834.
  8. ^ 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". Plant Archives. 20 (1): 417–429.
  9. ^ Nelson W, van Staden J (1985). "Aminocyclopropane-1-carboxylic acid in seaweed concentrate". Botanica Marina. 28 (9): 415-417. doi:10.1515/botm.1985.28.9.415.
  10. ^ Inanobe A, Furukawa H, Gouaux E (July 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. S2CID 16033761.
  11. ^ "Pesticide Experimental Use Permit; Receipt of Application; Comment Request" (PDF). Federal Register. 84 (152): 38624. August 7, 2019 – via www.govinfo.gov.


 

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March 14, 2024
aminocyclopropane, carboxylic, acid, disubstituted, cyclic, amino, acid, which, cyclopropane, ring, fused, atom, amino, acid, white, solid, many, cyclopropane, substituted, amino, acids, known, this, occurs, naturally, verification, needed, like, glycine, unli. 1 Aminocyclopropane 1 carboxylic acid ACC is a disubstituted cyclic a amino acid in which a cyclopropane ring is fused to the Ca atom of the amino acid It is a white solid Many cyclopropane substituted amino acids are known but this one occurs naturally 2 verification needed Like glycine but unlike most a amino acids ACC is not chiral 1 Aminocyclopropane 1 carboxylic acid NamesPreferred IUPAC name 1 Aminocyclopropane 1 carboxylic acidOther names 1 Aminocyclopropanecarboxylic acidIdentifiersCAS Number 22059 21 8 Y3D model JSmol 1 Interactive imageInteractive imageAbbreviations ACCChEBI CHEBI 58360 YChEMBL ChEMBL265325 YChemSpider 520 YDrugBank DB02085 YECHA InfoCard 100 108 227KEGG C01234 YPubChem CID 535UNII 3K9EJ633GL YCompTox Dashboard EPA DTXSID9039577InChI InChI 1S C4H7NO2 c5 4 1 2 4 3 6 7 h1 2 5H2 H 6 7 YKey PAJPWUMXBYXFCZ UHFFFAOYSA N YInChI 1 C4H7NO2 c5 4 1 2 4 3 6 7 h1 2 5H2 H 6 7 Key PAJPWUMXBYXFCZ UHFFFAOYAFSMILES 1 C O O C1 CC1 N O C O C1 N CC1PropertiesChemical formula C 4H 7N O 2Molar mass 101 1 cMelting point 198 201 C 388 394 F 471 474 K Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox referencesBiochemistry editACC is the precursor to the plant hormone ethylene 3 4 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 5 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 6 ACC can be used by soil microorganisms both bacteria and fungi as a source of nitrogen and carbon 7 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 7 8 ACC has also been extracted from kelp 9 ACC is also an exogenous partial agonist of the mammalian NMDA receptor 10 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 11 References edit Caspi R Foerster H Fulcher CA Hopkinson R Ingraham J Kaipa P et al January 2006 MetaCyc a multiorganism database of metabolic pathways and enzymes Nucleic Acids Research 34 Database issue D511 6 doi 10 1093 nar gkj128 PMC 1347490 PMID 16381923 Brackmann F de Meijere A November 2007 Natural Occurrence Syntheses and Applications of Cyclopropyl Group Containing a Amino Acids 1 1 Aminocyclopropanecarboxylic Acid and Other 2 3 Methanoamino Acids Chemical Reviews 107 11 4493 4537 doi 10 1021 cr078376j PMID 17944521 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 Kende H 1993 Ethylene biosynthesis Annu Rev Plant Physiol 44 283 307 doi 10 1146 annurev pp 44 060193 001435 Kende H September 1989 Enzymes of ethylene biosynthesis Plant Physiology 91 1 1 4 doi 10 1104 pp 91 1 1 PMC 1061940 PMID 16666977 Mou W Kao YT Michard E Simon AA Li D Wudick MM et al August 2020 Ethylene independent signaling by the ethylene precursor ACC in Arabidopsis ovular pollen tube attraction Nature Communications 11 1 4082 Bibcode 2020NatCo 11 4082M doi 10 1038 s41467 020 17819 9 PMC 7429864 PMID 32796832 a b Liu H Khan MY Carvalhais LC Delgado Baquerizo M Yan L Crawford M et al May 2019 Soil amendments with ethylene precursor alleviate negative impacts of salinity on soil microbial properties and productivity Scientific Reports 9 1 6892 Bibcode 2019NatSR 9 6892L doi 10 1038 s41598 019 43305 4 PMC 6499801 PMID 31053834 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 Plant Archives 20 1 417 429 Nelson W van Staden J 1985 Aminocyclopropane 1 carboxylic acid in seaweed concentrate Botanica Marina 28 9 415 417 doi 10 1515 botm 1985 28 9 415 Inanobe A Furukawa H Gouaux E July 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 S2CID 16033761 Pesticide Experimental Use Permit Receipt of Application Comment Request PDF Federal Register 84 152 38624 August 7 2019 via www govinfo gov nbsp This drug article relating to the nervous system is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title 1 Aminocyclopropane 1 carboxylic acid amp oldid 1175822807, wikipedia, wiki, book, books, library,

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