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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:
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 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

Certificates of Analysis (COA)

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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
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
L P Aiello et al.
Biochemistry, 25(13), 3944-3950 (1986-07-01)
Dipeptide substrates for metalloendoproteases have previously been shown to block biological processes requiring membrane fusion. Thus, we employed such compounds as potential inhibitors of the insulin-dependent activation of glucose transport in fat cells. This event is thought to involve vesicle
G W Booz et al.
Biochimica et biophysica acta, 1109(2), 132-140 (1992-08-24)
The characteristics of the process by which contraction enhances glucose transport in the frog sartorius were studied. Electrical stimulation increased the permeability of muscles to 3-O-methylglucose (3-O-MeGlc), a nonmetabolizable glucose analogue, increasing efflux as well as uptake. Enhanced efflux was
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