Tricholomic acid

Tricholomic acid is a non-proteinogenic amino acid found in some mushrooms, including Tricholoma muscarium.[1] It has a chemical structure similar to glutamic acid, hence the synonym cycloglutamate, and it interacts with glutamate receptors.[2] 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.[3]

Tricholomic acid
Names
IUPAC name
(2S)-2-Amino-2-[(5S)-3-oxo-1,2-oxazolidin-5-yl]acetic acid
Other names
α-Cycloglutamate; α-Amino-3-oxo-5-isoxazolidineacetic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
  • InChI=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
    Key: NTHMUJMQOXQYBR-OKKQSCSOSA-N
  • C1[C@H](ONC1=O)[C@@H](C(=O)O)N
Properties
C5H8N2O4
Molar mass 160.129 g·mol−1
Melting point 207 °C (405 °F; 480 K)[1] (decomp.)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

See also

References
  1. Takemoto, Tsunematsu; Nakajima, Tadashi (1964). "Studies on the Constituents of Indigenous Fungi. I". Yakugaku Zasshi. 84 (12): 1183. doi:10.1248/yakushi1947.84.12_1183.
  2. Tamborini, Lucia; Mastronardi, Federica; Lo Presti, Leonardo; Nielsen, Birgitte; De Micheli, Carlo; Conti, Paola; Pinto, Andrea (2017). "Synthesis of L-Tricholomic Acid Analogues and Pharmacological Characterization at Ionotropic Glutamate Receptors". ChemistrySelect. 2 (31): 10295. doi:10.1002/slct.201702154. hdl:2434/528800.
  3. Kuninaka, Akira (1969). "Recent Studies of 5′-Nucleotides as New Flavor Enhancers". Flavor Chemistry. Advances in Chemistry. 56: 261–274. doi:10.1021/ba-1966-0056.ch015. ISBN 0-8412-0057-2.
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