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Key Documents

G3291

Sigma-Aldrich

Glutamate, Caged hydrate

powder

Synonym(s):

(S)-Methyl 1-[5-(4-amino-4-carboxybutanoyl)]-7-nitroindoline-5-acetate hydrate, Caged Glutamate hydrate

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About This Item

Empirical Formula (Hill Notation):
C16H19N3O7 · xH2O
CAS Number:
Molecular Weight:
365.34 (anhydrous basis)
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

form

powder

color

light yellow

solubility

H2O: >10 mg/mL

storage temp.

−20°C

SMILES string

O.COC(=O)Cc1cc2CCN(C(=O)CC[C@H](N)C(O)=O)c2c(c1)[N+]([O-])=O

InChI

1S/C16H19N3O7.H2O/c1-26-14(21)8-9-6-10-4-5-18(15(10)12(7-9)19(24)25)13(20)3-2-11(17)16(22)23;/h6-7,11H,2-5,8,17H2,1H3,(H,22,23);1H2/t11-;/m0./s1

InChI key

GHHRKLFCIPHBAQ-MERQFXBCSA-N

Application

Glutamate, Caged hydrate has been used:
  • as a supplement in neurobasal medium for primary culture of mouse cortical neurons[1][2]
  • as a supplemental glutamate in laboratory-prepared food (LF)[3]
  • as a component of slicing solution used for perfusing the animal in mouse brain-slice experiments[4]

Biochem/physiol Actions

Caged glutamate is a photoactivatable compound. It is active on exposure to ultraviolet light.[5]
Glutamate derivative that is resistant to hydrolysis and biologically inert prior to photolysis.

Legal Information

Sold under license from the Medical Research Council

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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Role of mitochondrial calcium uniporter-mediated Ca2+ and iron accumulation in traumatic brain injury
Zhang LI, et al.
Journal of Cellular and Molecular Medicine, 23(4), 2995-3009 (2019)
In vitro imaging using laser photostimulation with flavoprotein autofluorescence
Theyel BB et al.
Nature Protocols, 6(4), 502-508 (2011)
Sodium aescinate provides neuroprotection in experimental traumatic brain injury via the Nrf2-ARE pathway
Zhang Li, et al.
Brain Research Bulletin, 157, 26-36 (2020)
Papageorgoiou, G.
Journal of the American Chemical Society, 121, 6503-6504 (1999)
Remote switching of cellular activity and cell signaling using light in conjunction with quantum dots
Lugo K, et al.
Biomedical Optics Express, 3(3), 447-454 (2012)

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