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359807

Sigma-Aldrich

Z-Phe-OH

99%

Synonym(s):

N-(Carbobenzyloxy)-L-phenylalanine, Z-L-Phenylalanine

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About This Item

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

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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Biochem/physiol Actions

Inhibitor of thermolysin

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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