tricholomic acid
{{Chembox
| ImageFile = Tricholomic acid.svg
| ImageSize = 200px
| IUPACName = (2S)-2-Amino-2-[(5S)-3-oxo-1,2-oxazolidin-5-yl]acetic acid
| OtherNames = α-Cycloglutamate; α-Amino-3-oxo-5-isoxazolidineacetic acid
| Section1 = {{Chembox Identifiers
| CASNo = 2644-49-7
| PubChem = 441456
| ChemSpiderID = 390188
| ChEBI = 9690
| ChEMBL = 260328
| KEGG = C08298
| StdInChI=1S/C5H8N2O4/c6-4(5(9)10)2-1-3(8)7-11-2/h2,4H,1,6H2,(H,7,8)(H,9,10)/t2-,4-/m0/s1
| StdInChIKey = NTHMUJMQOXQYBR-OKKQSCSOSA-N
| SMILES = C1[C@H](ONC1=O)[C@@H](C(=O)O)N
}}
| Section2 = {{Chembox Properties
| C=5|H=8|N=2|O=4
| Appearance =
| Density =
| MeltingPtC = 207
| MeltingPt_notes= (decomp.)
| BoilingPt =
| Solubility =
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| Section3 = {{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
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Tricholomic acid is a non-proteinogenic amino acid found in some mushrooms, including Tricholoma muscarium.{{Cite journal | doi = 10.1248/yakushi1947.84.12_1183| title = Studies on the Constituents of Indigenous Fungi. I| journal = Yakugaku Zasshi| volume = 84| issue = 12| pages = 1183–1186| year = 1964| last1 = Takemoto| first1 = Tsunematsu| last2 = Nakajima| first2 = Tadashi| doi-access = free| pmid = 14266548}} It has a chemical structure similar to glutamic acid, hence the synonym cycloglutamate, and it interacts with glutamate receptors.{{Cite journal | doi = 10.1002/slct.201702154| title = Synthesis of L-Tricholomic Acid Analogues and Pharmacological Characterization at Ionotropic Glutamate Receptors| journal = ChemistrySelect| volume = 2| issue = 31| pages = 10295| year = 2017| last1 = Tamborini| first1 = Lucia| last2 = Mastronardi| first2 = Federica| last3 = Lo Presti| first3 = Leonardo| last4 = Nielsen| first4 = Birgitte| last5 = De Micheli| first5 = Carlo| last6 = Conti| first6 = Paola| last7 = Pinto| first7 = Andrea| hdl = 2434/528800| hdl-access = free}} Because glutamate receptors are thought to be responsible for the reception of umami taste, tricholomic acid and close analogs have been investigated as flavor enhancers.{{Cite journal | doi = 10.1021/ba-1966-0056.ch015| title= Recent Studies of 5′-Nucleotides as New Flavor Enhancers| journal= Flavor Chemistry| volume = 56| pages = 261–274| series = Advances in Chemistry| year = 1969| last1 = Kuninaka| first1 = Akira| isbn = 0-8412-0057-2}}
See also
- Ibotenic acid, a related compound found in mushrooms
References
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External links
- [http://www.hmdb.ca/metabolites/HMDB0030412 Tricholomic acid], Human Metabolome Database