蓓豆氨酸

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]和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

^ ^1.0 ^1.1 Human Metabolome Database: Showing metabocard for Baikiain (HMDB0302856). [2024-02-29]. （原始內容存檔於2023-06-06）.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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).
^ 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.
^ 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.

[hmdb-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 . PMID 37255213. S2CID 258988288. doi:10.1021/acs.chemrestox.3c00100.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]