1-氨基環丙烷-1-甲酸

1-氨基環丙烷-1-甲酸
	IUPAC名; 1-Aminocyclopropane-1-carboxylic acid; 1-氨基環丙烷-1-甲酸
別名	1-氨基環丙烷甲酸
識別
縮寫	ACC
CAS號	22059-21-8
PubChem	535
ChemSpider	520
SMILES	C(O)(=O)C1(CC1)(N);
InChI	1/C4H7NO2/c5-4(1-2-4)3(6)7/h1-2,5H2,(H,6,7);
InChIKey	PAJPWUMXBYXFCZ-UHFFFAOYAF
ChEBI	58360
DrugBank	DB02085
KEGG	C01234
性質
化學式	C4H7NO2
摩爾質量	101.1 g·mol−1
熔點	198-201 °C（270 K）
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

1-氨基環丙烷-1-甲酸，簡稱ACC，是一種雙取代的環狀α-氨基酸，其中環丙烷環與氨基酸的C_α原子稠合。它是一種白色固體。目前已知有許多種環丙烷取代的氨基酸，但這種是天然存在的。^[2]與甘氨酸一樣，但與大多數α-氨基酸不同，ACC不是手性的。

Quick Facts 1-氨基環丙烷-1-甲酸, 識別 ...

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ACC是植物激素乙烯的前體。^[3]^[4]它由ACC合酶（EC 4.4.1.14）從甲硫氨酸合成，並通過ACC氧化酶（EC 1.14.17.4）轉化為乙烯。^[5]

ACC還表現出不依賴於乙烯的信號傳導，該信號通過激活類似於人類和動物神經系統反應所涉及的蛋白質，在授粉和種子生產中發揮關鍵作用。更具體地說，ACC信號促進花粉管趨化因子LURE1.2在胚珠孢子體組織中的分泌，從而增強花粉管的吸引力。此外，ACC通過根原生質體中的穀氨酸受體樣通道激活含Ca²⁺的離子流。^[6]

ACC可被土壤微生物（細菌和真菌）用作氮和碳的來源。^[7]因此，已證明使用ACC培養土壤可誘導編碼ACC脫氨作用的基因豐度，這可能對植物生長和脅迫耐受性產生積極影響。^[7]^[8]

ACC也曾從海帶中提取。^[9]

ACC也是哺乳動物 NMDA受體的外源性部分激動劑。^[10]

2019年，美國環境保護局發出通知，申請頒發ACC作為殺蟲劑的實驗使用許可證。^[11]

↑
Caspi R, Foerster H, Fulcher CA, Hopkinson R, Ingraham J, Kaipa P, et al. MetaCyc: a multiorganism database of metabolic pathways and enzymes. Nucleic Acids Research. January 2006, 34 (Database issue): D511–6. PMC 1347490 . PMID 16381923. doi:10.1093/nar/gkj128.
[2]
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. November 2007, 107 (11): 4493–4537. PMID 17944521. doi:10.1021/cr078376j.
[3]
Yang S, Hoffman N. Ethylene biosynthesis and its regulation in higher plants. Annu. Rev. Plant Physiol. 1984, 35: 155–189. doi:10.1146/annurev.pp.35.060184.001103.
[4]
Kende H. Ethylene biosynthesis. Annu. Rev. Plant Physiol. 1993, 44: 283–307. doi:10.1146/annurev.pp.44.060193.001435.
[5]
Kende H. Enzymes of ethylene biosynthesis. Plant Physiology. September 1989, 91 (1): 1–4. PMC 1061940 . PMID 16666977. doi:10.1104/pp.91.1.1.
[6]
Mou W, Kao YT, Michard E, Simon AA, Li D, Wudick MM, et al. Ethylene-independent signaling by the ethylene precursor ACC in Arabidopsis ovular pollen tube attraction. Nature Communications. August 2020, 11 (1): 4082. Bibcode:2020NatCo..11.4082M. PMC 7429864 . PMID 32796832. doi:10.1038/s41467-020-17819-9 .
[7]
Liu H, Khan MY, Carvalhais LC, Delgado-Baquerizo M, Yan L, Crawford M, et al. Soil amendments with ethylene precursor alleviate negative impacts of salinity on soil microbial properties and productivity. Scientific Reports. May 2019, 9 (1): 6892. Bibcode:2019NatSR...9.6892L. PMC 6499801 . PMID 31053834. doi:10.1038/s41598-019-43305-4.
[8]
Farahat MG, Mahmoud MK, Youseif SH, Saleh SA, Kamel Z. Alleviation of salinity stress in wheat by ACC deaminase-producing Bacillus aryabhattai EWR29 with multifarious plant growth-promoting attributes. Plant Archives. 2020, 20 (1): 417–429 [2023-03-06]. （原始內容存檔於2021-12-09）.
[9]
Nelson W, van Staden J. Aminocyclopropane-1-carboxylic acid in seaweed concentrate. Botanica Marina. 1985, 28 (9): 415-417. doi:10.1515/botm.1985.28.9.415.
[10]
Inanobe A, Furukawa H, Gouaux E. Mechanism of partial agonist action at the NR1 subunit of NMDA receptors. Neuron. July 2005, 47 (1): 71–84. PMID 15996549. S2CID 16033761. doi:10.1016/j.neuron.2005.05.022 .
[11]
Pesticide Experimental Use Permit; Receipt of Application; Comment Request (PDF). Federal Register. August 7, 2019, 84 (152): 38624 [2023-03-06]. （原始內容存檔 (PDF)於2023-04-17） –透過www.govinfo.gov.

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[pmid16381923-1] 
Caspi R, Foerster H, Fulcher CA, Hopkinson R, Ingraham J, Kaipa P, et al. MetaCyc: a multiorganism database of metabolic pathways and enzymes. Nucleic Acids Research. January 2006, 34 (Database issue): D511–6. PMC 1347490 . PMID 16381923. doi:10.1093/nar/gkj128.

[2] [2]
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. November 2007, 107 (11): 4493–4537. PMID 17944521. doi:10.1021/cr078376j.

[Yang_1984-3] [3]
Yang S, Hoffman N. Ethylene biosynthesis and its regulation in higher plants. Annu. Rev. Plant Physiol. 1984, 35: 155–189. doi:10.1146/annurev.pp.35.060184.001103.

[Kende_1993-4] [4]
Kende H. Ethylene biosynthesis. Annu. Rev. Plant Physiol. 1993, 44: 283–307. doi:10.1146/annurev.pp.44.060193.001435.

[Kende_1989-5] [5]
Kende H. Enzymes of ethylene biosynthesis. Plant Physiology. September 1989, 91 (1): 1–4. PMC 1061940 . PMID 16666977. doi:10.1104/pp.91.1.1.

[6] [6]
Mou W, Kao YT, Michard E, Simon AA, Li D, Wudick MM, et al. Ethylene-independent signaling by the ethylene precursor ACC in Arabidopsis ovular pollen tube attraction. Nature Communications. August 2020, 11 (1): 4082. Bibcode:2020NatCo..11.4082M. PMC 7429864 . PMID 32796832. doi:10.1038/s41467-020-17819-9 .

[Liu_2019-7] [7]
Liu H, Khan MY, Carvalhais LC, Delgado-Baquerizo M, Yan L, Crawford M, et al. Soil amendments with ethylene precursor alleviate negative impacts of salinity on soil microbial properties and productivity. Scientific Reports. May 2019, 9 (1): 6892. Bibcode:2019NatSR...9.6892L. PMC 6499801 . PMID 31053834. doi:10.1038/s41598-019-43305-4.

[8] [8]
Farahat MG, Mahmoud MK, Youseif SH, Saleh SA, Kamel Z. Alleviation of salinity stress in wheat by ACC deaminase-producing Bacillus aryabhattai EWR29 with multifarious plant growth-promoting attributes. Plant Archives. 2020, 20 (1): 417–429 [2023-03-06]. （原始內容存檔於2021-12-09）.

[9] [9]
Nelson W, van Staden J. Aminocyclopropane-1-carboxylic acid in seaweed concentrate. Botanica Marina. 1985, 28 (9): 415-417. doi:10.1515/botm.1985.28.9.415.

[pmid15996549-10] [10]
Inanobe A, Furukawa H, Gouaux E. Mechanism of partial agonist action at the NR1 subunit of NMDA receptors. Neuron. July 2005, 47 (1): 71–84. PMID 15996549. S2CID 16033761. doi:10.1016/j.neuron.2005.05.022 .

[11] [11]
Pesticide Experimental Use Permit; Receipt of Application; Comment Request (PDF). Federal Register. August 7, 2019, 84 (152): 38624 [2023-03-06]. （原始內容存檔 (PDF)於2023-04-17） –透過www.govinfo.gov.

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[5]

[6]

[7]

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[11]

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1-氨基環丙烷-1-甲酸

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參考資料

1-氨基環丙烷-1-甲酸

IUPAC名 1-Aminocyclopropane-1-carboxylic acid 1-氨基環丙烷-1-甲酸
別名	1-氨基環丙烷甲酸
識別
縮寫	ACC
CAS號	22059-21-8 ^Y
PubChem	535
ChemSpider	520
SMILES	C(O)(=O)C1(CC1)(N)
InChI	1/C4H7NO2/c5-4(1-2-4)3(6)7/h1-2,5H2,(H,6,7)
InChIKey	PAJPWUMXBYXFCZ-UHFFFAOYAF
ChEBI	58360
DrugBank	DB02085
KEGG	C01234
性質
化學式	C₄H₇NO₂
摩爾質量	101.1 g·mol⁻¹
熔點	198-201 °C（270 K）
若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。