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Sigma-Aldrich

4-Hydroxy-D-phenylglycine

≥98%

Synonym(s):

(2R)-2-Amino-2-(4-hydroxyphenyl)acetic acid

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About This Item

Linear Formula:
HOC6H4CH(NH2)CO2H
CAS Number:
22818-40-2
Molecular Weight:
167.16
Beilstein/REAXYS Number:
2210998
EC Number:
245-247-7
MDL number:
MFCD00004262
UNSPSC Code:
41116107
eCl@ss:
32160406
PubChem Substance ID:
24852886
NACRES:
NA.22

assay

≥98%

form

solid

optical activity

[α]23/D −158±3°, c = 1 in 1 M HCl

reaction suitability

reaction type: solution phase peptide synthesis

mp

240 °C (dec.) (lit.)

application(s)

peptide synthesis

SMILES string

N[C@@H](C(O)=O)c1ccc(O)cc1

InChI

1S/C8H9NO3/c9-7(8(11)12)5-1-3-6(10)4-2-5/h1-4,7,10H,9H2,(H,11,12)/t7-/m1/s1

InChI key

LJCWONGJFPCTTL-SSDOTTSWSA-N

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Storage Class

13 - Non 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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Stephan Kastner et al.
Archives of microbiology, 194(6), 557-566 (2012-02-07)
The nonproteinogenic amino acid 4-hydroxyphenylglycine (HPG) arises from the diversion of the tyrosine degradation pathway into secondary metabolism, and its biosynthesis requires a set of three enzymes. The gene cassette for HPG biosynthesis is widely spread in actinomycete bacteria, which
Mònica Prieto et al.
The Journal of organic chemistry, 74(23), 9202-9205 (2009-10-30)
Alpha-amino acid derivatives, particularly those of phenylglycine, can suffer significant racemization in Suzuki couplings. When arylpinacolboronate esters are used as coupling partners this unwanted side reaction can be suppressed by the use of Pd(OAc)(2) as Pd(0) source, in the presence
Jeanne M Davidsen et al.
Journal of bacteriology, 191(3), 1066-1077 (2008-11-26)
Nocardicin A is a monocyclic beta-lactam isolated from the actinomycete Nocardia uniformis, which shows moderate activity against a broad spectrum of gram-negative bacteria. Within the biosynthetic gene cluster of nocardicin A, nocR encodes a 583-amino-acid protein with high similarity to
Naotoshi Hirota et al.
Life sciences, 79(13), 1312-1316 (2006-05-19)
To assess the mechanism of beta-cell lipotoxicity in comparison with Fas-mediated cell death, we used a mouse beta-cell clone stably transfected with human Fas. Palmitate induced beta-cell death in correlation with medium glucose levels between 5 and 20 mmol/l, while
Gerald Maarman et al.
Cardiovascular drugs and therapy, 26(3), 205-216 (2012-03-13)
By increasing circulating free fatty acids and the rate of fatty acid oxidation, obesity decreases glucose oxidation and myocardial tolerance to ischemia. Partial inhibition of fatty acid oxidation may improve myocardial tolerance to ischemia/reperfusion (I/R) in obesity. We assessed the
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