Lac-Phe

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).

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, though intraperitoneal injection does reduce food intake and weight gain.[1]

See also

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References

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  1. ^ a b c Li VL, He Y, Contrepois K, Liu H, Kim JT, Wiggenhorn AL, et al. (June 2022). "An exercise-inducible metabolite that suppresses feeding and obesity". Nature. 606 (7915): 785–790. Bibcode:2022Natur.606..785L. doi:10.1038/s41586-022-04828-5. PMC 9767481. PMID 35705806. S2CID 249710767.
  2. ^ Wong C (15 June 2022). "Appetite-suppressing molecule helps obese mice lose weight". New Scientist. Retrieved 18 June 2022.
  3. ^ Reynolds G (15 June 2022). "Why Does a Hard Workout Make You Less Hungry?". The New York Times. Retrieved 18 June 2022.
  4. ^ Hoene M, Zhao X, Machann J, Birkenfeld AL, Heni M, Peter A, et al. (January 2023). "Exercise-Induced N-Lactoylphenylalanine Predicts Adipose Tissue Loss during Endurance Training in Overweight and Obese Humans". Metabolites. 13 (1): 15. doi:10.3390/metabo13010015. PMC 9863672. PMID 36676940. S2CID 255077184.
  5. ^ Jansen RS, Addie R, Merkx R, Fish A, Mahakena S, Bleijerveld OB, et al. (May 2015). "N-lactoyl-amino acids are ubiquitous metabolites that originate from CNDP2-mediated reverse proteolysis of lactate and amino acids". Proceedings of the National Academy of Sciences of the United States of America. 112 (21): 6601–6606. Bibcode:2015PNAS..112.6601J. doi:10.1073/pnas.1424638112. PMC 4450436. PMID 25964343.
  6. ^ "Metabocard for N-Lactoylphenylalanine". The Human Metabolome Database (HMDB). The Metabolomics Innovation Centre (TIMC). HMDB0062175.
  7. ^ Wu J, Gao J, Lin J, Cui C, Li L, He S, Brennan C (May 2022). "Preparation and Taste Characteristics of Kokumi N-Lactoyl Phenylalanine in the Presence of Phenylalanine and Lactate". Journal of Agricultural and Food Chemistry. 70 (17): 5396–5407. doi:10.1021/acs.jafc.2c00530. PMID 35452224. S2CID 248345604.
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