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860794

Sigma-Aldrich

Z-L-Phe chloromethyl ketone

98%

Synonym(s):

N-Carbobenzyloxy-L-phenylalanyl chloromethyl ketone, NSC 251810, SL-01, ZPCK

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About This Item

Linear Formula:
C6H5CH2CH(NHCO2CH2C6H5)COCH2Cl
CAS Number:
26049-94-5
Molecular Weight:
331.79
EC Number:
247-432-8
MDL number:
MFCD00037114
UNSPSC Code:
12352204
PubChem Substance ID:
24888520
NACRES:
NA.22

Assay

98%

form

powder

optical activity

[α]23/D +30°, c = 1 in chloroform

reaction suitability

reaction type: solution phase peptide synthesis

mp

107-108 °C (lit.)

application(s)

peptide synthesis

storage temp.

−20°C

SMILES string

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

InChI

1S/C18H18ClNO3/c19-12-17(21)16(11-14-7-3-1-4-8-14)20-18(22)23-13-15-9-5-2-6-10-15/h1-10,16H,11-13H2,(H,20,22)/t16-/m0/s1

InChI key

OYHLRJGDELITAF-INIZCTEOSA-N

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Application

Enzyme inhibitor.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

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)

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G Jung et al.
Protein science : a publication of the Protein Society, 4(11), 2433-2435 (1995-11-01)
The essential histidine residue of carboxypeptidase Y (CPY) was modified by a site-specific reagent, a chloromethylketone derivative of benzyloxycarbonyl-L-phenylalanine. The single modified histidine residue was converted to N tau-carboxy-methyl histidine (cmHis) upon performic acid oxidation. A peptide containing cmHis was
L A Johnson et al.
Biochimica et biophysica acta, 953(3), 269-279 (1988-04-14)
The reaction of chymase, a chymotryptic proteinase from human skin, and bovine pancreatic chymotrypsin with a number of time-dependent inhibitors has been studied. An integrated equation, relating product formation with time, has been derived for the reaction of enzymes with
Inhibition of carboxypeptidase Y by chloromethyl ketone derivatives of benzyloxycarbonyl-L-phenylalanine.
R Hayashi et al.
Journal of biochemistry, 76(6), 1355-1357 (1974-12-01)
Biogenesis of vaccina: interrelationship between post-translational cleavage, virus assembly, and maturation.
M Silver et al.
Virology, 117(2), 341-356 (1982-03-01)
T Wileman et al.
Cell regulation, 2(9), 753-765 (1991-09-01)
The endoplasmic reticulum, or an organelle closely associated with it, contains proteases that can be used to remove partially assembled or improperly folded proteins. Very little is known at present about the types of protease that degrade these proteins. The
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