All Photos(1)
Synonym(s):
α-Me-D-Phe-OH, (R)-(+)-2-Amino-2-methyl-3-phenylpropionic acid
Empirical Formula (Hill Notation):
C10H13NO2
CAS Number:
Molecular Weight:
179.22
Beilstein:
5254151
MDL number:
UNSPSC Code:
12352209
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
Quality Level
Assay
≥98.0% (HPLC)
form
powder
optical purity
ee: ≥98.0% (HPLC)
reaction suitability
reaction type: solution phase peptide synthesis
application(s)
peptide synthesis
SMILES string
C[C@@](N)(Cc1ccccc1)C(O)=O
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
InChI key
HYOWVAAEQCNGLE-SNVBAGLBSA-N
Related Categories
Signal Word
Warning
Hazard Statements
Hazard Classifications
Acute Tox. 4 Oral
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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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
Adverse effects of excessive consumption of amino acids.
N J Benevenga et al.
Annual review of nutrition, 4, 157-181 (1984-01-01)
M Castillo et al.
Neurochemical research, 13(6), 547-550 (1988-06-01)
Supplementation of 5% phenylalanine plus 0.4% alpha-methylphenylalanine to the standard diet or 1% phenylalanine plus 0.08% alpha-methylphenylalanine to the drinking water produced phenylketonuria-like conditions in 5-day-old chicks. An increase of 10 to 15-fold in the phenylalanine content was observed in
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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