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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:
Molecular Weight:
356.37
Beilstein:
2182728
EC Number:
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
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 Code

13 - Non 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

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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
C D McCallum et al.
Biochemistry, 34(6), 1815-1824 (1995-02-14)
Many membrane functions are modulated by the bulk biophysical properties of the membrane. Various compounds which alter membrane physical properties were investigated for their ability to modulate insulin receptor autophosphorylation and signaling. Compounds which raise the bilayer to hexagonal phase
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
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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