Baikiain Explained

Baikiain is an organic compound with the molecular formula . Chemically, it is classified as a tetrahydropyridine substituted with a carboxylic acid. Because it contains both this carboxylic acid and an adjacent amine group, it is also an alpha-amino acid.[1] Baikiain is one of the two enantiomers of the chiral compound 4,5-didehydropipecolic acid.

Sources

Baikiain has been found in diverse natural sources including dates,[1] African teak (Baikiaea plurijuga) wood,[2] and the red algae Serraticardia maxima.[3]

Several laboratory syntheses of baikiain and its racemic form have been reported.[4] [5] [6] [7]

Effects

Baikiain is hypothesized to be the causative agent of illnesses resulting from consumption of food products containing tara flour.[8]

Notes and References

  1. Web site: Human Metabolome Database: Showing metabocard for Baikiain (HMDB0302856) .
  2. 10.1039/JR9500003590 . 709. The chemistry of extractives from hardwoods. Part III. Baikiain, an amino-acid present in Baikiaea plurijuga . 1950 . King . F. E. . King . T. J. . Warwick . A. J. . Journal of the Chemical Society (Resumed) . 3590 .
  3. 10.1080/00021369.1980.10864393 . Identification ofl-Baikiain from Calcareous Red Algae Serraticardia maxima(Yendo) Silva and Its Distribution in Some Rhodophyta . 1980 . Maeda . Masaakira . Hasegawa . Yoshikazu . Hashimoto . Hisanobu . Agricultural and Biological Chemistry . 44 . 11 . 2725–2737 .
  4. 10.1021/jo01074a001 . A Direct Synthesis of DL-Baikiain . 1960 . Burgstahler . Albert W. . Aiman . Charles E. . The Journal of Organic Chemistry . 25 . 4 . 489–492 .
  5. 10.1016/S0040-4039(01)02271-7 . Straightforward entry to the pipecolic acid nucleus. Enantioselective synthesis of baikiain . 2002 . Ginesta . Xavier . Pericàs . Miquel A. . Riera . Antoni . Tetrahedron Letters . 43 . 5 . 779–782 .
  6. 10.3987/COM-06-10874 . Synthesis of Pipecolic Acid and Baikiain . 2006 . Chang . Meng-Yang . Kung . Yung-Hua . Wu . Tsun-Cheng . Heterocycles . 68 . 11 . 2365 . 2024-02-17 . free .
  7. 10.1002/jhet.4648 . Synthesis of cyclic amino acid baikiain via asymmetric phase transfer catalysis . 2023 . Espinoza-Hicks . José C. . Chávez-Flores . David . Galán . Gerardo Zaragoza . Camacho-Dávila . Alejandro A. . Journal of Heterocyclic Chemistry . 60 . 6 . 1027–1031 . 257784165 .
  8. 10.1021/acs.chemrestox.3c00100 . 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 . 2023 . 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. . Chemical Research in Toxicology . 36 . 6 . 818–821 . 37255213 . 258988288 . 10283043 .

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