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Merck
CN

79840

N-Phthaloyl-L-glutamic acid

purum, ≥98.0% (T)

Synonym(s):

PhGA

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About This Item

Empirical Formula (Hill Notation):
C13H11NO6
CAS Number:
Molecular Weight:
277.23
PubChem Substance ID:
UNSPSC Code:
12352200
Beilstein/REAXYS Number:
90136
MDL number:
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grade

purum

assay

≥98.0% (T)

optical activity

[α]20/D −48±2°, c = 3% in dioxane

mp

160-162 °C

application(s)

peptide synthesis

SMILES string

OC(=O)CC[C@H](N1C(=O)c2ccccc2C1=O)C(O)=O

InChI

1S/C13H11NO6/c15-10(16)6-5-9(13(19)20)14-11(17)7-3-1-2-4-8(7)12(14)18/h1-4,9H,5-6H2,(H,15,16)(H,19,20)/t9-/m0/s1

InChI key

FEFFSKLJNYRHQN-VIFPVBQESA-N

Other Notes

N-protected derivative of L-glutamic acid. The anhydride (prepared with DCCI or Ac2O without racemization) is used for γ-L-glutamylations; The phthaloyl protection can be removed mildly


Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Agaridoxin, a mushroom metabolite. Isolation, structure, and synthesis.
A Szent-Gyorgyi et al.
The Journal of organic chemistry, 41(9), 1603-1606 (1976-04-30)
-Glutamyl cyclotransferase. Distribution, isozymic forms, and specificity.
M Orlowski et al.
The Journal of biological chemistry, 248(8), 2836-2844 (1973-04-25)
Isolation and structure of coprine, the in vivo aldehyde dehydrogenase inhibitor in Coprinus atramentarius; Syntheses of coprine and related cyclopropa4one derivatives.
P Lindberg et al.
Journal of the Chemical Society. Perkin transactions 1, (6), 684-691 (1977-01-01)