Names | |
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IUPAC name
(2S)-2-[[(2S)-2-hydroxypropanoyl]amino]-3-phenylpropanoic acid
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Other names
N-[(S)-lactoyl]-L-phenylalaninate
N-Lactoyl-phenylalanine N-Lactoylphenylalanine | |
Identifiers | |
3D model (JSmol)
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ChEBI | |
ChemSpider | |
PubChem CID
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Properties | |
C12H15NO4 | |
Molar mass | 237.255 g·mol−1 |
Related compounds | |
Related N-acyl-alpha-amino acids
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N-Acetylaspartic acid N-acetylcysteine N-Acetylglutamic acid N-Acetylglutamine N-Acetylleucine N-formylmethionine |
Related compounds
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Lactamide |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Lactoylphenylalanine, or Lac-Phe, is a metabolite generated by intense exercise.[1][2][3] In mice, high levels of Lac-Phe in the blood cause a decrease of food intake[1] and in humans, its production has been shown to correlate with adipose tissue loss during an endurance exercise intervention.[4] In mammals it is created from (S)-lactate and L-phenylalanine by the cytosol nonspecific dipeptidase (CNDP2) protein.[5] It is classified as N-acyl-alpha-amino acid and pseudodipeptide.[6]
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.[7] Oral intake of Lac-Phe does not have anti-obesity effects in mice.[1]