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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 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]

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]

  1. ^ a b c 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.
  2. ^ Sgarbi, Elisa; Lazzi, Camilla; Iacopino, Luca; Bottesini, Chiara; Lambertini, Francesca; Sforza, Stefano; Gatti, Monica (2013-09-01). "Microbial origin of non proteolytic aminoacyl derivatives in long ripened cheeses". Food Microbiology. 35 (2): 116–120. doi:10.1016/j.fm.2013.02.013. ISSN 0740-0020.
  3. ^ Bottesini, Chiara; Tedeschi, Tullia; Dossena, Arnaldo; Sforza, Stefano (2014-02-01). "Enzymatic production and degradation of cheese-derived non-proteolytic aminoacyl derivatives". Amino Acids. 46 (2): 441–447. doi:10.1007/s00726-013-1637-3. ISSN 1438-2199.
  4. ^ Feng, Junwei; Huang, Zikun; Huang, Mingtao; Cui, Chun; Zhao, Mouming; Feng, Yunzi (2024-11-30). "Revealing the Microbial Origins of N-Lactoyl Amino Acids in Soy Sauce: Synthesis Conditions, Potential Enzymes, and Utilization Preference". Journal of Agricultural and Food Chemistry. doi:10.1021/acs.jafc.4c04907. ISSN 0021-8561.
  5. ^ Xiao, Shuke; Li, Veronica L.; Long, Jonathan Z. (2024-08-01). "Lac-Phe (N-lactoyl-phenylalanine)". Trends in Endocrinology & Metabolism. 35 (8): 758–759. doi:10.1016/j.tem.2024.05.007. ISSN 1043-2760. PMID 39137723.
  6. ^ 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.
  7. ^ Wong C (15 June 2022). "Appetite-suppressing molecule helps obese mice lose weight". New Scientist. Retrieved 18 June 2022.
  8. ^ Reynolds G (15 June 2022). "Why Does a Hard Workout Make You Less Hungry?". The New York Times. Retrieved 18 June 2022.
  9. ^ Václavík, Jan; Coene, Karlien L. M.; Vrobel, Ivo; Najdekr, Lukáš; Friedecký, David; Karlíková, Radana; Mádrová, Lucie; Petsalo, Aleksanteri; Engelke, Udo F. H.; van Wegberg, Annemiek; Kluijtmans, Leo A. J.; Adam, Tomáš; Wevers, Ron A. (2018). "Structural elucidation of novel biomarkers of known metabolic disorders based on multistage fragmentation mass spectra". Journal of Inherited Metabolic Disease. 41 (3): 407–414. doi:10.1007/s10545-017-0109-4. ISSN 1573-2665.
  10. ^ 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.
  11. ^ "Metabocard for N-Lactoylphenylalanine". The Human Metabolome Database (HMDB). The Metabolomics Innovation Centre (TIMC). HMDB0062175.
  12. ^ Feng, Junwei; Huang, Zikun; Cui, Chun; Zhao, Mouming; Feng, Yunzi (2024-10-01). "Synthesis, taste characteristics and taste mechanism of N-lactoyl leucine from soy sauce using sensory analysis and UPLC-MS/MS". Food Chemistry. 454: 139670. doi:10.1016/j.foodchem.2024.139670. ISSN 0308-8146.
  13. ^ 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.
  14. ^ Sforza, Stefano; Cavatorta, Valeria; Galaverna, Gianni; Dossena, Arnaldo; Marchelli, Rosangela (2009-10-01). "Accumulation of non-proteolytic aminoacyl derivatives in Parmigiano-Reggiano cheese during ripening". International Dairy Journal. 19 (10): 582–587. doi:10.1016/j.idairyj.2009.04.009. ISSN 0958-6946.
  15. ^ Moya-Garzon MD, Wang M, Li VL, Lyu X, Wei W, Tung AS; et al. (2024). "A β-hydroxybutyrate shunt pathway generates anti-obesity ketone metabolites". Cell. doi:10.1016/j.cell.2024.10.032. PMID 39536746.{{cite journal}}: CS1 maint: multiple names: authors list (link)
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