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Key Documents

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690791

Sigma-Aldrich

α-Methyl-D-phenylalanine

≥98.0% (HPLC)

Sinónimos:

α-Me-D-Phe-OH, (R)-(+)-2-Amino-2-methyl-3-phenylpropionic acid

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About This Item

Fórmula empírica (notación de Hill):
C10H13NO2
Número de CAS:
17350-84-4
Peso molecular:
179.22
Beilstein/REAXYS Number:
5254151
MDL number:
MFCD00153491
UNSPSC Code:
12352209
PubChem Substance ID:
329761363
NACRES:
NA.22

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

Categorías relacionadas

Pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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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
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
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