L-Phenylalanine  (Synonyms: Phenylalanine)

L-Phenylalanine ((S)-2-Amino-3-phenylpropionic acid) is an essential amino acid isolated from Escherichia coli. L-Phenylalanine is a α2δ subunit of voltage-dependent Ca⁺ channels antagonist with a K_i of 980 nM. L-phenylalanine is a competitive antagonist for the glycine- and glutamate-binding sites of N-methyl-D-aspartate receptors (NMDARs) (K_B of 573 μM ) and non-NMDARs, respectively. L-Phenylalanine is widely used in the production of food flavors and pharmaceuticals^[1][2][3][4].

DAHP synthetase (DS) and chorismate mutase/prephenate dehydratase (CM/PD) are key enzymes in the L-Phenylalanine biosynthesis pathway. DS is sensitive to feedback inhibition by tyrosine, and CM/PD is subject to feedback inhibition by L-Phenylalanine^[1]. L-Phenylalanine attenuates non-NMDA receptor function in cultured neurons with an IC₅₀ of 980 μM^[5].

MCE has not independently confirmed the accuracy of these methods. They are for reference only.

The effects of L-Phenylalanine on NMDA-activated currents (I_NMDA) are studied in cultured hippocampal neurons from newborn rats using the patch-clamp technique. L-Phenylalanine specifically and reversibly attenuates I_NMDA in a concentration-dependent manner (IC₅₀ of 1.71 mM). L-Phenylalanine inhibits specifically NMDAR current in hippocampal neurons by competing for the glycine-binding site^[3].

MCE has not independently confirmed the accuracy of these methods. They are for reference only.

165.19

Solid

C₉H₁₁NO₂

63-91-2

N[C@@H](CC1=CC=CC=C1)C(O)=O

Room temperature in continental US; may vary elsewhere.

• [1]. Glushakov AV, et al. Long-term changes in glutamatergic synaptic transmission in phenylketonuria. Brain. 2005 Feb;128(Pt 2):300-7.  [Content Brief]

  [2]. Glushakov AV, et al. L-phenylalanine selectively depresses currents at glutamatergic excitatory synapses. J Neurosci Res. 2003 Apr 1;72(1):116-24.  [Content Brief]

  [3]. Glushakov AV, et al. Specific inhibition of N-methyl-D-aspartate receptor function in rat hippocampal neurons by L-phenylalanine at concentrations observed during phenylketonuria. Mol Psychiatry. 2002;7(4):359-67.  [Content Brief]

  [4]. Mortell KH, et al. Structure-activity relationships of alpha-amino acid ligands for the alpha2delta subunit of voltage-gated calcium channels. Bioorg Med Chem Lett. 2006 Mar 1;16(5):1138-41.  [Content Brief]

  [5]. Wu WB, et al. Enhancement of l-phenylalanine production in Escherichia coli by heterologous expression of Vitreoscilla hemoglobin. Biotechnol Appl Biochem. 2018 May;65(3):476-483.  [Content Brief]