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Lac-Phe
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    Lac-Phe

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    Lac-Phe
    Lac-Phe.svg
    Names
    IUPAC name
    (2S)-2-[[(2S)-2-hydroxypropanoyl]amino]-3-phenylpropanoic acid
    Other names
    N-[(S)-lactoyl]-L-phenylalaninate
    N-Lactoyl-phenylalanine
    N-Lactoylphenylalanine
    Identifiers
    3D model (JSmol)
    ChEBI
    ChemSpider
    PubChem CID
    • InChI=1S/C12H15NO4/c1-8(14)11(15)13-10(12(16)17)7-9-5-3-2-4-6-9/h2-6,8,10,14H,7H2,1H3,(H,13,15)(H,16,17)/t8-,10-/m0/s1
      Key: IIRJJZHHNGABMQ-WPRPVWTQSA-N
    • C[C@@H](C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O)O
    Properties
    C12H15NO4
    Molar mass 237.255 g·mol−1
    Related compounds
    Related N-acyl-alpha-amino acids
    N-Acetylaspartic acid
    N-acetylcysteine
    N-Acetylglutamic acid
    N-Acetylglutamine
    N-Acetylleucine
    N-formylmethionine
    Related compounds
    Lactamide
    Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

    Lactoylphenylalanine, or Lac-Phe, is a metabolite generated by intense exercise. In mice, high levels of Lac-Phe in the blood cause a decrease of food intake. In mammals it is created from (S)-lactate and L-phenylalanine by the cytosol nonspecific dipeptidase (CNDP2) protein. It is classified as N-acyl-alpha-amino acid and pseudodipeptide.

    It has also been reported that as an additive N-L-lactoyl phenylalanine improves the taste of food, conferring an umami flavor. It is found naturally in significant amounts in some traditional Chinese fermented foods such as preserved pickles and soy sauce.

    See also

    External links


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