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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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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
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 A Phillips et al.
Biochemistry, 31(4), 959-963 (1992-02-04)
A new strategy of potentially broad application for probing transition-state (TS) analogy in enzymatic systems is described in this paper. The degree to which a series of phosphonate inhibitors act as TS analogues of rat carboxypeptidase A1 has been determined
P A Bartlett et al.
Biochemistry, 21(7), 1608-1611 (1982-03-30)
Carbobenzoxythioglycyl-L-phenylalanine [CbzNHCH2C(==S)Phe, Z-Glys-Phe] was synthesized as thioamide analogue of Z-Gly-Phe, a known substrate of carboxypeptidase A (CPA). By use of a ninhydrin-based assay and Z-Gly-Gly-Phe as the substrate, Z-Glys-Phe was shown to be a weak competitive inhibitor of CPA (Ki

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