Lac-Phe

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 and in humans, its production has been shown to correlate with adipose tissue loss during an endurance exercise intervention. 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.

Lac-Phe
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
SMILES
  • 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).
Infobox references

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. Oral intake of Lac-Phe does not have anti-obesity effects in mice, though intraperitoneal injection does reduce food intake and weight gain.

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