A8378
DL-2-Allylglycine
Synonym(s):
(±)-2-Amino-4-pentenoic acid, DL-C-Allylglycine
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About This Item
Linear Formula:
H2C=CHCH2CH(NH2)CO2H
CAS Number:
Molecular Weight:
115.13
NACRES:
NA.26
PubChem Substance ID:
eCl@ss:
32160406
UNSPSC Code:
12352200
EC Number:
231-689-8
MDL number:
Beilstein/REAXYS Number:
1748645
InChI key
WNNNWFKQCKFSDK-UHFFFAOYSA-N
InChI
1S/C5H9NO2/c1-2-3-4(6)5(7)8/h2,4H,1,3,6H2,(H,7,8)
SMILES string
NC(CC=C)C(O)=O
assay
≥98% (TLC)
form
powder
color
white
mp
258-260 °C (lit.)
application(s)
peptide synthesis
storage temp.
−20°C
Biochem/physiol Actions
DL-2-Allylglycine is a racemic mixture of L- and D-allylglycine. D-allylglycine is the enantiomer of L-allylglycine, a glutamate decarboxylase (GAD) inhibitor used in GABA research. D-allylglycine may be used as a control supplement versus L-allylglycine in GABA research. D-allylglycine is used in the organic synthesis of cyclic opioid peptide agonists and antagonists.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Faceshields, Gloves
Regulatory Information
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S Moyanova et al.
Acta physiologica et pharmacologica Bulgarica, 15(1), 47-53 (1989-01-01)
The effect of DL-allylglycine (DL-AG) in two doses (40 and 60 mg/kg i.v.) was studied on cats under acute conditions. DL-AG provoked the appearance of epileptiform EEG patterns either spontaneous or in response to intermittent light stimulation with a frequency
Non-centrosymmetric racemates: space-group frequencies and conformational similarities between crystallographically independent molecules.
Dalhus B, Gorbitz CH.
Acta Physiologica Et Pharmacologica Bulgarica, 56, 715-719 (2000)
D A Kunz et al.
Journal of bacteriology, 148(1), 72-82 (1981-10-01)
Spontaneous mutants which acquired the ability to utilize d-allylglycine (d-2-amino-4-pentenoic acid) and dl-cis-crotylglycine (dl-2-amino-cis-4-hexenoic acid) but not l-allylglycine or dl-trans-crotylglycine could be readily isolated from Pseudomonas putida mt-2 (PaM1). Derivative strains of PaM1 putatively cured of the TOL (pWWO) plasmid
Pl Johnson et al.
Journal of psychopharmacology (Oxford, England), 22(6), 642-652 (2008-03-01)
Panic patients are vulnerable to induction of panic attacks by sub-threshold interoceptive stimuli such as intravenous (i.v.) sodium lactate infusions. Facilitation of serotonergic signaling with selective serotonin reuptake inhibitors can suppress anxiety and panic-like responses, but the mechanisms involved are
Irena Berezowska et al.
Chemical biology & drug design, 74(4), 329-334 (2009-08-22)
The opioid peptide H-Tyr-c[D-Cys-Phe-Phe-Cys]NH(2) cyclized via a methylene dithiother is a potent and selective mu opioid agonist (Przydial M.J. et al., J Peptide Res, 66, 2005, 255). Dicarba analogues of this peptide with Tyr, 2',6'-dimethyltyrosine (Dmt), 3-[2,6-dimethyl-4-hydroxyphenyl)propanoic acid (Dhp) or
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