蓓豆氨酸

蓓豆氨酸(英语:Baikiain)是一种有机化合物,分子式为C6H9NO2。在化学上,它被归类为被羧酸取代的四氢吡啶。因为它同时含有该羧酸和相邻的氨基,所以它也是一种α-氨基酸[1]蓓豆氨酸是手性化合物4,5-二脱氢哌啶甲酸的两种对映体之一。

蓓豆氨酸
IUPAC名
(2S)-1,2,3,6-Tetrahydropyridine-2-carboxylic acid
别名 (-)-(S)-Baikiain; L-Baikiain; (S)-4,5-Didehydropipecolic acid
识别
CAS号 31456-71-0
PubChem 441442
ChemSpider 390175
SMILES
 
  • C1C=CCN[C@@H]1C(=O)O
ChEBI 6199
KEGG C08268
性质
化学式 C6H9NO2
摩尔质量 127.14 g·mol−1
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。

来源

蓓豆氨酸存在于多种天然来源中,包括椰枣[1]Baikiaea plurijuga英语Baikiaea plurijuga木材[2]Serraticardia maxima[3]

已报道了几种蓓豆氨酸及其外消旋形式的实验室合成方法。[4][5][6][7]

影响

据推测,因食用含有塔拉粉英语Tara spinosa的食品而引起疾病的病原体很可能就是蓓豆氨酸。[8]

参考资料

  1. ^ 1.0 1.1 Human Metabolome Database: Showing metabocard for Baikiain (HMDB0302856). [2024-02-29]. (原始内容存档于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 (不活跃 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 . PMID 37255213. S2CID 258988288. doi:10.1021/acs.chemrestox.3c00100.