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96260

Sigma-Aldrich

Z-Gly-Phe

≥99.0%

Synonym(s):

Z-glycyl-L-phenylalanine

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About This Item

Linear Formula:
C6H5CH2OOCNHCH2CONHCH(CH2C6H5)COOH
CAS Number:
1170-76-9
Molecular Weight:
356.37
Beilstein/REAXYS Number:
2182728
EC Number:
214-626-9
MDL number:
MFCD00037264
UNSPSC Code:
12352200
PubChem Substance ID:
57653752
NACRES:
NA.22

assay

≥99.0%

form

powder

optical activity

[α]20/D +40±1°, c = 2.5% in ethanol

reaction suitability

reaction type: solution phase peptide synthesis

mp

125-132 °C

application(s)

peptide synthesis

SMILES string

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

InChI

1S/C19H20N2O5/c22-17(12-20-19(25)26-13-15-9-5-2-6-10-15)21-16(18(23)24)11-14-7-3-1-4-8-14/h1-10,16H,11-13H2,(H,20,25)(H,21,22)(H,23,24)/t16-/m0/s1

InChI key

FLGYJBNDDWLTQR-INIZCTEOSA-N

Other Notes

Z-protected dipeptide employed in the Anteunis′ test to determine racemization in peptide coupling

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
BCBS6763V
BCBN7238V
BCBK7063V
BCBH5673V
BCBC1314V

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G Kuznetsov et al.
The Journal of biological chemistry, 267(6), 3932-3939 (1992-02-25)
HepG2 cells were employed as model system to investigate potential relationships between early protein processing and Ca2+ storage by the endoplasmic reticulum. Ca2+ was required for glycoprotein processing and export by intact cells. The processing and export of alpha 1-antitrypsin
R A Firestone et al.
Journal of medicinal chemistry, 25(5), 539-544 (1982-05-01)
Bioactive primary and secondary amines, when acylated with the Z-Gly-Phe group, are transported into pinocytic cells, such as macrophages, P-815 mastocytoma, SV-40 3T3, and leukemia 1210, much faster than the parent compounds. Amines such as lysosomotropic detergents [R. A. Firestone
T J Wheeler
Biochimica et biophysica acta, 979(3), 331-340 (1989-03-13)
Three compounds which inhibit glucose transport in rat adipocytes have been proposed to act directly on the glucose transporter protein. We tested these proposals by examining the effects of the compounds on the stereospecific glucose uptake catalyzed by adipocyte membrane
J L Roe et al.
Experimental cell research, 181(2), 542-550 (1989-04-01)
Metalloendoproteases have been implicated in a variety of fusion processes including plasma membrane fusion and exocytosis. As a prerequisite to skeleton formation in the sea urchin embryo, primary mesenchyme cells undergo fusion via filopodia to form syncytia. The spicule is
M Roth et al.
Clinica chimica acta; international journal of clinical chemistry, 135(1), 65-71 (1983-11-30)
A method has been designed for the assay of pancreatic carboxypeptidase A in blood serum. It uses Z-Gly-Phe as the substrate and fluorimetric determination of the released phenylalanine in an amino acid analyser, which yields a measure of free carboxypeptidase
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