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Merck
CN

78570

D-(−)-α-Phenylglycine

puriss., ≥99.0% (NT)

Synonym(s):

(2R)-2-Amino-2-phenylacetic acid, (R)-(−)-α-Aminophenylacetic acid

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About This Item

Empirical Formula (Hill Notation):
C8H9NO2
CAS Number:
875-74-1
Molecular Weight:
151.16
EC Number:
212-876-3
UNSPSC Code:
12352200
PubChem Substance ID:
329768163
Beilstein/REAXYS Number:
2208676
MDL number:
MFCD00008061

Key Documents

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InChI key

ZGUNAGUHMKGQNY-SSDOTTSWSA-N

InChI

1S/C8H9NO2/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7H,9H2,(H,10,11)/t7-/m1/s1

SMILES string

N[C@@H](C(O)=O)c1ccccc1

grade

puriss.

assay

≥99.0% (NT)

optical activity

[α]20/D −156±2°, c = 1% in 1 M HCl

ign. residue

≤0.05%

mp

≥300 °C (dec.)

application(s)

peptide synthesis

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Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

302.0 °F - closed cup

flash_point_c

150 °C - closed cup

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Motohiro Akazome et al.
The Journal of organic chemistry, 75(3), 660-665 (2010-01-07)
In terms of chiral recognition for racemic aryl methyl sulfoxides in the solid state, three kinds of crystalline (S)-alkylglycyl-(S)-phenylglycines were examined as potential dipeptides host molecules. When (S)-alanyl-(S)-phenylglycines [(S,S)-Ala-Phg] crystallized with aryl methyl sulfoxides, the stereochemistry of preferentially included sulfoxides
Jian-Lian Chen et al.
Analytica chimica acta, 718, 130-137 (2012-02-07)
Three different approaches for immobilizing cross-linked chitosan molecules (CS-s) in sol-gel phases to form chiral OT-CEC capillaries were comparatively investigated in this study. To synthesize column I, a bare capillary was first silanized with triethoxysilane (TEOS) and then reacted with
Lu Wang et al.
Enzyme and microbial technology, 51(2), 107-112 (2012-06-06)
α-Amino acid ester hydrolases (AEHs) are enzymes of interest to the semi-synthesis of β-lactam antibiotics with α-amino, such as cephalexin and cefaclor. An undesired side reaction, the hydrolysis of α-amino acid ester, had hindered applications in antibiotics synthesis. Although the
James J Lynch et al.
Pain, 125(1-2), 136-142 (2006-06-20)
Gabapentin and pregabalin have been demonstrated, both in animal pain models and clinically, to be effective analgesics particularly for the treatment of neuropathic pain. The precise mechanism of action for these two drugs is unknown, but they are generally believed
Ulrike Müller et al.
Metabolic engineering, 8(3), 196-208 (2006-02-10)
D-phenylglycine (D-Phg) is an important side chain building block for semi-synthetic penicillins and cephalosporins such as ampicillin and cephalexin. To produce d-Phg ultimately from glucose, metabolic engineering was applied. Starting from phenylpyruvate, which is the direct precursor of L-phenylalanine, an
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