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Lac-Phe

Chemical compound From Wikipedia, the free encyclopedia

Lactoylphenylalanine, or Lac-Phe, is an N-lactoyl-amino acid metabolite produced by mammals and microorganisms.[1][2][3][4][5] In humans, levels are increased by intense exercise and in the inborn error of metabolism phenylketonuria.[6][7][8][1][9] In mice, high levels of Lac-Phe in the blood cause a decrease of food intake[6] and in humans, its production has been shown to correlate with adipose tissue loss during an endurance exercise intervention.[10] In mammals it is created from (S)-lactate and L-phenylalanine by the cytosol nonspecific dipeptidase (CNDP2) protein.[1] It is classified as N-acyl-alpha-amino acid and pseudodipeptide.[11]

Quick facts Names, Identifiers ...
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
  • 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).
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It has also been reported that as an additive, N-L-lactoyl phenylalanine improves the taste of food, conferring an umami flavor.[12] It is found naturally in significant amounts in some traditional Chinese fermented foods such as preserved pickles and soy sauce,[13] and in Parmigiano-Reggiano cheese.[14] Oral intake of Lac-Phe does not have anti-obesity effects in mice, though intraperitoneal injection does reduce food intake and weight gain.[6] Activity dependent cell labeling indicates Lac-Phe activated neural populations in the hypothalamus and brainstem. [15]

Lac-Phe was discovered as a hormone at Stanford University in 2022.[16][17][6] It is released during intense exercise and after eating and reduces appetite and obesity in animals.[16][18][17][6] Besides metabolic effects, Lac-Phe has also been found to produce anxiolytic-like effects in rodents, which were associated with dopaminergic and serotonergic signaling as well as reduced hippocampal cytokine expression.[19] Lac-Phe itself has poor pharmacokinetic properties, for instance a short duration.[18][20] A synthetic alternative known as ENV-308 suitable for once-daily oral administration is described as an exercise mimetic and is under formal clinical development as of 2026.[21]

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