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A8378

Sigma-Aldrich

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:
7685-44-1
Molecular Weight:
115.13
Beilstein:
1748645
EC Number:
231-689-8
MDL number:
MFCD00063103
UNSPSC Code:
12352200
eCl@ss:
32160406
PubChem Substance ID:
24891336
NACRES:
NA.26

Assay

≥98% (TLC)

form

powder

color

white

mp

258-260 °C (lit.)

application(s)

peptide synthesis

storage temp.

−20°C

SMILES string

NC(CC=C)C(O)=O

InChI

1S/C5H9NO2/c1-2-3-4(6)5(7)8/h2,4H,1,3,6H2,(H,7,8)

InChI key

WNNNWFKQCKFSDK-UHFFFAOYSA-N

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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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H317,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - 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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
M Bottlaender et al.
European journal of pharmacology, 321(1), 13-17 (1997-02-19)
The influence of decreased endogenous gamma-aminobutyric acid (GABA) concentration on benzodiazepine receptor function was studied in the brain of living baboons. Positron emission tomography and the radiotracer [11C]flumazenil combined with electroencephalography were used to determine the pharmacological properties of two
Tadashi Saigusa et al.
Neuropharmacology, 62(2), 907-913 (2011-10-04)
GABA released from accumbal GABAergic interneurons plays an inhibitory role in the regulation of dopamine efflux through GABA(B) and GABA(A) receptors located on accumbal dopaminergic nerve endings. The cytosolic newly synthesised GABA alters vesicular GABA levels and, accordingly, the amount
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
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