690791
α-Methyl-D-phenylalanine
≥98.0% (HPLC)
Synonym(s):
α-Me-D-Phe-OH, (R)-(+)-2-Amino-2-methyl-3-phenylpropionic acid
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About This Item
Empirical Formula (Hill Notation):
C10H13NO2
CAS Number:
Molecular Weight:
179.22
UNSPSC Code:
12352209
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
5254151
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Product Name
α-Methyl-D-phenylalanine, ≥98.0% (HPLC)
InChI
1S/C10H13NO2/c1-10(11,9(12)13)7-8-5-3-2-4-6-8/h2-6H,7,11H2,1H3,(H,12,13)/t10-/m1/s1
SMILES string
C[C@@](N)(Cc1ccccc1)C(O)=O
InChI key
HYOWVAAEQCNGLE-SNVBAGLBSA-N
assay
≥98.0% (HPLC)
form
powder
optical purity
ee: ≥98.0% (HPLC)
reaction suitability
reaction type: solution phase peptide synthesis
application(s)
peptide synthesis
Quality Level
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Shinya Oishi et al.
Journal of medicinal chemistry, 48(3), 764-772 (2005-02-04)
Previous work has shown that incorporation of either 1-aminocyclohexanecarboxylic acid (Ac6c) or alpha-methyl-p-phosphonophenylalanine ((alpha-Me)Ppp) in the phosphotyrosyl (pTyr) C-proximal position (pY + 1 residue) of Grb2 SH2 domain binding peptides confers high affinity. The tetralin-based (S)-2-amino-6-phosphonotetralin-2-carboxylic acid (Atc(6-PO3H2)) simultaneously presents
C A Brass et al.
The Biochemical journal, 208(3), 765-771 (1982-12-15)
Hyperphenylalaninaemia induced by daily injections of alpha-methylphenylalanine plus phenylalanine caused 20-40% decreases in cerebral dopamine (3,4-dihydroxyphenethylamine) and noradrenaline in 7- and 11-day-old rats. alpha-Methylphenylalanine alone as well as phenylalanine alone caused cerebral dopamine depletion. However, the effects were not additive
O Greengard et al.
Neurochemical research, 9(6), 837-848 (1984-06-01)
Brain phenylalanine concentrations at plasma levels raised to that in phenylketonuric subjects were studied in rats from fetal through postnatal life. Suppression of the hepatic phenylalanine hydroxylase with alpha methylphenylalanine, and injections of age-adjusted doses of phenylalanine on the next
Adverse effects of excessive consumption of amino acids.
N J Benevenga et al.
Annual review of nutrition, 4, 157-181 (1984-01-01)
C Toniolo et al.
Peptide research, 5(1), 56-61 (1992-01-01)
We have synthesized, by solution methods, and fully characterized a variety of (alpha Me)Phe derivatives and model peptides (to the pentapeptide level). The results of the solution conformational analysis, performed by using infrared absorption and 1H nuclear magnetic resonance, support
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