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L-Phenylalanine-d8

CAT: 0804-HY-N0215S1-01Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-N0215S1-01Size:1 mg
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Description
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].
CAS Number
17942-32-4
Product Name Alternative
(S) -2-Amino-3-phenylpropionic acid-d8
UNSPSC
12352005
Hazard Statement
H302, H315, H319, H335
Target
Calcium Channel; Endogenous Metabolite; iGluR
Type
Isotope-Labeled Compounds
Related Pathways
Membrane Transporter/Ion Channel; Metabolic Enzyme/Protease; Neuronal Signaling
Field of Research
Metabolic Disease
Purity
99.90
Solubility
10 mM in DMSO|H2O : 6.67mg/mL (ultrasonic)
Smiles
OC([C@](N)([2H])C([2H])([2H])C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H])=O
Molecular Formula
C9H3D8NO2
Molecular Weight
173.24
Precautions
H302, H315, H319, H335
References & Citations
[1]Russak EM, et al. Impact of Deuterium Substitution on the Pharmacokinetics of Pharmaceuticals. Ann Pharmacother. 2019;53 (2) :211-216. |[2]Glushakov AV, et al. Long-term changes in glutamatergic synaptic transmission in phenylketonuria. Brain. 2005 Feb;128 (Pt 2) :300-7.|[3]Glushakov AV, et al. L-phenylalanine selectively depresses currents at glutamatergic excitatory synapses. J Neurosci Res. 2003 Apr 1;72 (1) :116-24.|[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.|[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.|[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.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Isotope-Labeled Compounds
Clinical Information
No Development Reported
Isoform
NMDA Receptor

Chemical Information

L-Phenyl-d5-alanine-2,3,3-d3
CAS Number17942-32-4
PubChem CID13000987
IUPAC Name(2S)-2-amino-2,3,3-trideuterio-3-(2,3,4,5,6-pentadeuteriophenyl)propanoic acid
Molecular FormulaC9H11NO2
Molecular Weight173.24
XLogP-1.5
Topological Polar Surface Area63.3
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count3
Rotatable Bond Count3
Heavy Atom Count12
Formal Charge0
Complexity153
SMILES
[2H]C1=C(C(=C(C(=C1[2H])[2H])C([2H])([2H])[C@@]([2H])(C(=O)O)N)[2H])[2H]
InChI
InChI=1S/C9H11NO2/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8H,6,10H2,(H,11,12)/t8-/m0/s1/i1D,2D,3D,4D,5D,6D2,8D
InChIKey
COLNVLDHVKWLRT-WYMAAGAPSA-N
Chemical Structure
2D Structure
2D structure of L-Phenyl-d5-alanine-2,3,3-d3
CAS: 17942-32-4
CID: 13000987
Formula: C9H11NO2
MW: 173.24
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight173.24
XLogP3-1.5
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count3
Rotatable Bond Count3
Exact Mass173.129192561
Monoisotopic Mass173.129192561
Topological Polar Surface Area63.3 Ų
Heavy Atom Count12
Formal Charge0
Complexity153
Isotope Atom Count8
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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Alternative Products

CatalogName
TRC-P319419-25MGL-Phenylalanine-d8
sc-489918N-FMOC-L-phenylalanine-d8
AR-P31236-01L-Phenylalanine-13C9-15N-d8
MBS6038959-01Melphalan-d8 (4-[Bis(2-chloroethyl)amino]-L-phenylalanine-d8, p-Di-(2-chloroethyl)amino-L-phenylalanine-d8, L-phenylalanine Mustard-d8, Alanine Nitrogen Mustard-d8, L-PAM-d8, Melfalan-d8, Alkeran-d8, Sarcoclorin-d8)
M2872-05AMelphalan-d8 (4-[Bis (2-chloroethyl) amino]-L-phenylalanine-d8, p-Di- (2-chloroethyl) amino-L-phenylalanine-d8, L-phenylalanine Mustard-d8, Alanine Nitrogen Mustard-d8, L-PAM-d8, Melfalan-d8, Alkeran-d8, Sarcoclorin-d8) discontinued
CS-T-84204DL-Phenylalanine-d8
AR-P31247-01D-Phenylalanine-d8
DE2112DL-3-Phenylalanine-D8
PB0422L-Phenylalanine
11557-32L- (-) -Phenylalanine

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