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蓓豆氨酸

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蓓豆氨酸
IUPAC名
(2S)-1,2,3,6-Tetrahydropyridine-2-carboxylic acid
別名 (-)-(S)-Baikiain; L-Baikiain; (S)-4,5-Didehydropipecolic acid
識別
CAS號 31456-71-0
PubChem 441442
ChemSpider 390175
SMILES
 
  • C1C=CCN[C@@H]1C(=O)O
ChEBI 6199
KEGG C08268
性質
化學式 C6H9NO2
摩爾質量 127.14 g·mol−1
若非註明,所有數據均出自標準狀態(25 ℃,100 kPa)下。

蓓豆氨酸(英語:Baikiain)是一種有機化合物,分子式為C6H9NO2。在化學上,它被歸類為被羧酸取代的四氫吡啶。因為它同時含有該羧酸和相鄰的氨基,所以它也是一種α-胺基酸[1]蓓豆氨酸是手性化合物4,5-二脫氫哌啶甲酸的兩種對映體之一。

來源

蓓豆氨酸存在於多種天然來源中,包括椰棗[1]Baikiaea plurijuga英語Baikiaea plurijuga木材[2]Serraticardia maxima[3]

已報道了幾種蓓豆氨酸及其外消旋形式的實驗室合成方法。[4][5][6][7]

影響

據推測,因食用含有塔拉粉英語Tara spinosa的食品而引起疾病的病原體很可能就是蓓豆氨酸。[8]

參考資料

  1. ^ 1.0 1.1 Human Metabolome Database: Showing metabocard for Baikiain (HMDB0302856). [2024-02-29]. (原始內容存檔於2023-06-06). 
  2. ^ King, F. E.; King, T. J.; Warwick, A. J. 709. The chemistry of extractives from hardwoods. Part III. Baikiain, an amino-acid present in Baikiaea plurijuga. Journal of the Chemical Society (Resumed). 1950: 3590. doi:10.1039/JR9500003590. 
  3. ^ Maeda, Masaakira; Hasegawa, Yoshikazu; Hashimoto, Hisanobu. Identification ofl-Baikiain from Calcareous Red Algae Serraticardia maxima(Yendo) Silva and Its Distribution in Some Rhodophyta. Agricultural and Biological Chemistry. 1980, 44 (11): 2725–2737. doi:10.1080/00021369.1980.10864393. 
  4. ^ Burgstahler, Albert W.; Aiman, Charles E. A Direct Synthesis of DL-Baikiain. The Journal of Organic Chemistry. 1960, 25 (4): 489–492. doi:10.1021/jo01074a001. 
  5. ^ Ginesta, Xavier; Pericàs, Miquel A.; Riera, Antoni. Straightforward entry to the pipecolic acid nucleus. Enantioselective synthesis of baikiain. Tetrahedron Letters. 2002, 43 (5): 779–782. doi:10.1016/S0040-4039(01)02271-7. 
  6. ^ Chang, Meng-Yang; Kung, Yung-Hua; Wu, Tsun-Cheng. Synthesis of Pipecolic Acid and Baikiain. Heterocycles. 2006, 68 (11): 2365. doi:10.3987/COM-06-10874 (不活躍 2024-02-17). 
  7. ^ Espinoza-Hicks, José C.; Chávez-Flores, David; Galán, Gerardo Zaragoza; Camacho-Dávila, Alejandro A. Synthesis of cyclic amino acid baikiain via asymmetric phase transfer catalysis. Journal of Heterocyclic Chemistry. 2023, 60 (6): 1027–1031. S2CID 257784165. doi:10.1002/jhet.4648. 
  8. ^ Chittiboyina, Amar G.; Ali, Zulfiqar; Avula, Bharathi; Khan, Shabana I.; Mir, Tahir M.; Zhang, Jin; Aydoğan, Fadime; Zulfiqar, Fazila; Techen, Natascha; Parveen, Iffat; Pandey, Pankaj; Adams, Sebastian J.; Wang, Yan-Hong; Zhao, Jianping; Marshall, Gailen D.; Pugh, Nirmal D.; Khan, Ikhlas A. Is Baikiain in Tara Flour a Causative Agent for the Adverse Events Associated with the Recalled Frozen French Lentil & Leek Crumbles Food Product? - A Working Hypothesis. Chemical Research in Toxicology. 2023, 36 (6): 818–821. PMC 10283043可免費查閱. PMID 37255213. S2CID 258988288. doi:10.1021/acs.chemrestox.3c00100.