1-氨基环丙烷-1-甲酸
化合物
(重定向自1-氨基环丙烷-1-羧酸)
1-氨基环丙烷-1-甲酸,简称ACC,是一种双取代的环状α-氨基酸,其中环丙烷环与氨基酸的Cα原子稠合。它是一种白色固体。目前已知有许多种环丙烷取代的氨基酸,但这种是天然存在的。[2]与甘氨酸一样,但与大多数α-氨基酸不同,ACC不是手性的。
1-氨基环丙烷-1-甲酸 | |
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IUPAC名 1-Aminocyclopropane-1-carboxylic acid 1-氨基环丙烷-1-甲酸 | |
别名 | 1-氨基环丙烷甲酸 |
识别 | |
缩写 | ACC |
CAS号 | 22059-21-8 |
PubChem | 535 |
ChemSpider | 520 |
SMILES |
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InChI |
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InChIKey | PAJPWUMXBYXFCZ-UHFFFAOYAF |
ChEBI | 58360 |
DrugBank | DB02085 |
KEGG | C01234 |
性质 | |
化学式 | C4H7NO2 |
摩尔质量 | 101.1 g·mol−1 |
熔点 | 198-201 °C(270 K) |
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。 |
生物化学
ACC是植物激素乙烯的前体。[3][4]它由ACC合酶(EC 4.4.1.14)从甲硫氨酸合成,并通过ACC氧化酶(EC 1.14.17.4)转化为乙烯。[5]
ACC还表现出不依赖于乙烯的信号传导,该信号通过激活类似于人类和动物神经系统反应所涉及的蛋白质,在授粉和种子生产中发挥关键作用。更具体地说,ACC信号促进花粉管趋化因子LURE1.2在胚珠孢子体组织中的分泌,从而增强花粉管的吸引力。此外,ACC通过根原生质体中的谷氨酸受体样通道激活含Ca2+的离子流。[6]
ACC可被土壤微生物(细菌和真菌)用作氮和碳的来源。[7]因此,已证明使用ACC培养土壤可诱导编码ACC脱氨作用的基因丰度,这可能对植物生长和胁迫耐受性产生积极影响。[7][8]
参考资料
- ^ 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.
- ^ 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 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 H. Ethylene biosynthesis. Annu. Rev. Plant Physiol. 1993, 44: 283–307. doi:10.1146/annurev.pp.44.060193.001435.
- ^ 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.
- ^ 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 .
- ^ 7.0 7.1 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.
- ^ 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]. (原始内容存档于2021-12-09).
- ^ 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.
- ^ 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 .
- ^ Pesticide Experimental Use Permit; Receipt of Application; Comment Request (PDF). Federal Register. August 7, 2019, 84 (152): 38624 [2023-03-06]. (原始内容存档 (PDF)于2023-04-17) –通过www.govinfo.gov.
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