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| 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 | |
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| 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]
Contents
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]