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286656

Sigma-Aldrich

α-Methyl-DL-phenylalanine

98%

Synonym(s):

(±)-2-Amino-2-methyl-3-phenylpropionic acid

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About This Item

Linear Formula:
C6H5CH2C(CH3)(NH2)CO2H
CAS Number:
1132-26-9
Molecular Weight:
179.22
Beilstein/REAXYS Number:
2803960
MDL number:
MFCD00010512
UNSPSC Code:
12352209
PubChem Substance ID:
24857247
NACRES:
NA.22

assay

98%

reaction suitability

reaction type: solution phase peptide synthesis

mp

293-294 °C (dec.) (lit.)

application(s)

peptide synthesis

SMILES string

CC(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)

InChI key

HYOWVAAEQCNGLE-UHFFFAOYSA-N

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Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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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 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
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 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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