L-Phenylalanine-d₈  (Synonyms: (S)-2-Amino-3-phenylpropionic acid-d₈)

L-Phenylalanine-d₈ is the deuterium labeled L-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 Ki of 980 nM. L-phenylalanine is a competitive antagonist for the glycine- and glutamate-binding sites of N-methyl-D-aspartate receptors (NMDARs) (KB of 573 μM ) and non-NMDARs, respectively. L-Phenylalanine is widely used in the production of food flavors and pharmaceuticals[1][2][3][4].

Stable heavy isotopes of hydrogen, carbon, and other elements have been incorporated into drug molecules, largely as tracers for quantitation during the drug development process. Deuteration has gained attention because of its potential to affect the pharmacokinetic and metabolic profiles of drugs^[1].

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

173.24

C₉H₃D₈NO₂

17942-32-4

Solid

White to off-white

OC([C@](N)([2H])C([2H])([2H])C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H])=O

Room temperature in continental US; may vary elsewhere.

• [1]. Russak EM, et al. Impact of Deuterium Substitution on the Pharmacokinetics of Pharmaceuticals. Ann Pharmacother. 2019;53(2):211-216.  [Content Brief]

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

  [3]. 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]

  [4]. 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]

  [5]. 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]

  [6]. 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]