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359807

Sigma-Aldrich

Z-Phe-OH

99%

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Synonym(s):
N-(Carbobenzyloxy)-L-phenylalanine, Z-L-Phenylalanine
Linear Formula:
C6H5CH2CH(NHCOOCH2C6H5)COOH
CAS Number:
1161-13-3
Molecular Weight:
299.32
Beilstein:
2222826
EC Number:
214-599-3
MDL number:
MFCD00020418
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
24862110
NACRES:
NA.22

Quality Level

200

Assay

99%

optical activity

[α]20/D +5°, c = 5 in acetic acid

reaction suitability

reaction type: solution phase peptide synthesis

mp

85-87 °C (lit.)

application(s)

peptide synthesis

SMILES string

OC(=O)[C@H](Cc1ccccc1)NC(=O)OCc2ccccc2

InChI

1S/C17H17NO4/c19-16(20)15(11-13-7-3-1-4-8-13)18-17(21)22-12-14-9-5-2-6-10-14/h1-10,15H,11-12H2,(H,18,21)(H,19,20)/t15-/m0/s1

InChI key

RRONHWAVOYADJL-HNNXBMFYSA-N

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Related Categories

Biochem/physiol Actions

Inhibitor of thermolysin

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Dhruvkumar Soni et al.
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While antiretroviral therapy (ART) has revolutionized treatment and prevention of human immunodeficiency virus type one (HIV-1) infection, regimen adherence, viral mutations, drug toxicities and access stigma and fatigue are treatment limitations. These have led to new opportunities for the development
B Harris et al.
Biochimica et biophysica acta, 889(1), 1-5 (1986-10-31)
The possible role of metalloendoproteinase in stimulus-secretion coupling in adrenal chromaffin cells was examined using the metalloendoproteinase inhibitors 1,10-phenanthroline and carbobenzoxy-Gly-Phe-NH2. Catecholamine release elicited by nicotine or by depolarisation with 55 mM K+ was almost completely abolished by 0.5 mM
S Stoeva
International journal of peptide and protein research, 37(4), 325-330 (1991-04-01)
Diethylpyrocarbonate (DEPC) inactivated the neutral zinc proteinase from Bacillus mesentericus strain 76/Bacillus subtilis (MCP 76) by ethoxycarbonylation completely. Exposure of the enzyme to DEPC together with the competitive inhibitor Z-L-phenylalanine prevented the loss of activity toward both peptide and protein
J Wiese et al.
Biomedica biochimica acta, 50(10-11), S90-S93 (1991-01-01)
The alpha-glyceryl esters of Z-Gly, Z-Phe and Z-Tyr were synthesized and their use for protease catalyzed peptide synthesis was studied. Three enzymes isolated from crude papain were compared in their catalytic potency. Syntheses with alpha-chymotrypsin were performed in a biphasic
Mariangela Ceruso et al.
Biochimica et biophysica acta, 1824(2), 303-310 (2011-11-01)
The chemical shift of the carboxylate carbon of Z-tryptophan is increased from 179.85 to 182.82 ppm and 182.87 ppm on binding to thermolysin and stromelysin-1 respectively. The chemical shift of Z-phenylalanine is also increased from 179.5 ppm to 182.9 ppm
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