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Key Documents

217034

Sigma-Aldrich

β-Methyl-DL-phenylalanine hydrochloride

99%, Mixture of ~67% threo, ~33% erythro

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About This Item

Linear Formula:
C6H5CH(CH3)CH(NH2)CO2H · HCl
CAS Number:
Molecular Weight:
215.68
EC Number:
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:

Assay

99%

mp

210 °C (dec.) (lit.)

SMILES string

Cl.CC(C(N)C(O)=O)c1ccccc1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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A Péter et al.
Journal of chromatography. A, 728(1-2), 455-465 (1996-03-29)
Erythro-D,L- and threo-D,L-beta-methylphenylalanine, -beta-methyltyrosine and -beta-methyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid were synthesized. High-performance liquid chromatographic methods were developed for the separation and identification of the enantiomers of the beta-methyl amino acids, with the application of 1-fluoro-2,4-dinitrophenyl-5-L-alanine amide and 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl isothiocyanate as derivatizing reagents.
Lisa M Nogle et al.
Journal of pharmaceutical and biomedical analysis, 40(4), 901-909 (2005-10-22)
A direct preparative purification of all four isomers of the unnatural amino acid beta-methylphenylalanine was achieved using supercritical fluid chromatography (SFC) with stacked-injection. Final purification of the Cbz-methyl ester derived isomers was performed on a Daicel Chiralpak AD-H column (20
H I Mosberg et al.
Journal of medicinal chemistry, 37(25), 4384-4391 (1994-12-09)
The in vitro pharmacological properties and conformational features of analogs of the delta opioid receptor selective tetrapeptide Tyr-c[D-Cys-Phe-D-Pen]OH (JOM-13) in which the Phe3 residue was replaced by each of the four stereoisomers of beta-methylphenylalanine (beta-MePhe) were investigated. Both analogs in
A Péter et al.
Journal of chromatography. A, 705(2), 267-273 (1995-06-30)
A reversed-phase high-performance liquid chromatographic (RP-HPLC) method was developed to obtain pure erythro[2S3S, 2R3R]- and threo[2S3R, 2R3S]-beta-methylphenylalanine. These amino acids were incorporated into an enkephalin, H-Tyr-D-Ala-Gly-beta-MePhe-Val-Val-Gly-NH2, and into a deltorphin C, H-Tyr-D-Ala-beta-MePhe-Asp-Val-Val-Gly-NH2, analogue, which yielded four diastereoisomers of the peptides.
A Misicka et al.
The journal of peptide research : official journal of the American Peptide Society, 50(1), 48-54 (1997-07-01)
Using the method of conformational constraint, we have designed and synthesized analogues of deltorphin I and dermenkephalin containing each of the four stereoisomers (2S,3S; 2S,3R; 2R,3S; 2R,3R) of the unusual amino acid beta-methylphenylalanine in position three. The potency and selectivity

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