蓓豆氨酸

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。

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。

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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]和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]
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.

[hmdb-1] [1]
Human Metabolome Database: Showing metabocard for Baikiain (HMDB0302856). [2024-02-29]. （原始内容存档于2023-06-06）.

[2] [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] [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] [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] [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] [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] [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] [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.

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