L-Phenylalanine

Cat No.:V29806 Purity: ≥98%
L-Phenylalanine ((S)-2-Amino-3-phenylpropionic acid) is an essential amino acid (AA) extracted from Escherichia coli.
L-Phenylalanine Chemical Structure CAS No.: 63-91-2
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1g
Other Sizes

Other Forms of L-Phenylalanine:

  • H-Phe-OBzl.HCl
  • L-Phenylalanine-d7 ((S)-2-Amino-3-phenylpropionic acid-d7)
  • L-Phenylalanine-d8 ((S)-2-Amino-3-phenylpropionic acid-d8)
  • L-Phenylalanine-13C9,15N ((S)-2-Amino-3-phenylpropionic acid-13C9,15N)
  • L-Phenylalanine-d5 (L-phenylalanine-d5)
  • L-Phenylalanine-d2 ((S)-2-Amino-3-phenylpropionic acid-d2)
  • DL-Phenylalanine-d5 (2-Amino-3-phenylpropionic acid-d5)
  • L-Phenylalanine-3-13C ((S)-2-Amino-3-phenylpropionic acid-3-13C)
  • L-Phenylalanine-13C9 ((S)-2-Amino-3-phenylpropionic acid-13C9)
  • L-Phenylalanine-d ((S)-2-Amino-3-phenylpropionic acid-d1)
  • L-Phenylalanine-13C ((S)-2-Amino-3-phenylpropionic acid-13C)
  • L-Phenylalanine-15N ((S)-2-Amino-3-phenylpropionic acid-15N)
  • L-Phenylalanine-13C6 ((S)-2-Amino-3-phenylpropionic acid-13C6)
  • L-Phenylalanine-13C9,15N,d8 ((S)-2-Amino-3-phenylpropionic acid-13C9,15N,d8)
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Top Publications Citing lnvivochem Products
Product Description
L-Phenylalanine ((S)-2-Amino-3-phenylpropionic acid) is an essential amino acid (AA) extracted from Escherichia coli. L-Phenylalanine is a voltage-dependent α2δ subunit Ca2+ channel antagonist (inhibitor) with Ki of 980 nM. L-Phenylalanine is a competitive antagonist of the glycine and glutamate binding sites of NMDARs (KB 573 μM) and non-NMDARs. L-Phenylalanine is extensively used in the production/synthesis of food flavors and pharmaceuticals.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
Important players in the biosynthesis of L-phenylalanine include DAHP synthase (DS) and chorismate mutase/prephenylate dehydratase (CM/PD). While CM/PD is susceptible to feedback inhibition by L-phenylalanine, DS is susceptible to feedback inhibition by tyrosine [1]. With an IC50 of 980 μM, L-phenylalanine can reduce the activity of non-NMDA receptors in cultured neurons [5].
ln Vivo
The patch-clamp method was used to examine the impact of L-phenylalanine on NMDA-activated currents (INMDA) in cultured rat hippocampus neurons. With an IC50 of 1.71 mM, L-phenylalanine selectively and reversibly reduces IMDA in a concentration-dependent manner. By competing with glycine binding sites, L-phenylalanine selectively suppresses NMDAR currents in hippocampus neurons [3].
References
[1]. Glushakov AV, et al. Long-term changes in glutamatergic synaptic transmission in phenylketonuria. Brain. 2005 Feb;128(Pt 2):300-7.
[2]. Glushakov AV, et al. L-phenylalanine selectively depresses currents at glutamatergic excitatory synapses. J Neurosci Res. 2003 Apr 1;72(1):116-24.
[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.
[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.
[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.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C9H11NO2
Molecular Weight
165.1891
CAS #
63-91-2
Related CAS #
L-Phenylalanine benzyl ester hydrochloride;2462-32-0;L-Phenylalanine-d7;69113-60-6;L-Phenylalanine-d8;17942-32-4;L-Phenylalanine-13C9,15N;878339-23-2;L-Phenylalanine-d5;56253-90-8;L-Phenylalanine-d2;221346-31-2;DL-Phenylalanine-d5;284664-89-7;L-Phenylalanine-3-13C;136056-02-5;L-Phenylalanine-13C9;439685-11-7;L-Phenylalanine-d;54793-54-3;L-Phenylalanine-15N,d8;L-Phenylalanine-13C;81201-86-7;L-Phenylalanine-15N;29700-34-3;DL-Phenylalanine-d5 hydrochloride;L-Phenylalanine-13C6;180268-82-0;L-Phenylalanine-13C9,15N,d8;1994331-22-4
SMILES
O([H])C([C@]([H])(C([H])([H])C1C([H])=C([H])C([H])=C([H])C=1[H])N([H])[H])=O
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
H2O : ~6.67 mg/mL (~40.38 mM)
Solubility (In Vivo)
Solubility in Formulation 1: 9.09 mg/mL (55.03 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication (<60°C).

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 6.0536 mL 30.2682 mL 60.5364 mL
5 mM 1.2107 mL 6.0536 mL 12.1073 mL
10 mM 0.6054 mL 3.0268 mL 6.0536 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
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