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A8137

Sigma-Aldrich

D-Allylglycine

≥98% (TLC)

Synonym(s):

(R)-(+)-2-Amino-4-pentenoic acid, D-2-Amino-4-pentenoic acid

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About This Item

Empirical Formula (Hill Notation):
C5H9NO2
CAS Number:
54594-06-8
Molecular Weight:
115.13
Beilstein/REAXYS Number:
1721511
MDL number:
MFCD00063104
UNSPSC Code:
12352209
PubChem Substance ID:
24891321
NACRES:
NA.26

product name

D-Allylglycine,

assay

≥98% (TLC)

form

powder

color

white

application(s)

cell analysis
peptide synthesis

storage temp.

−20°C

SMILES string

N[C@H](CC=C)C(O)=O

InChI

1S/C5H9NO2/c1-2-3-4(6)5(7)8/h2,4H,1,3,6H2,(H,7,8)/t4-/m1/s1

InChI key

WNNNWFKQCKFSDK-SCSAIBSYSA-N

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Biochem/physiol Actions

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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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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
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
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
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
Stephan Urwyler et al.
Journal of medicinal chemistry, 52(16), 5093-5107 (2009-08-01)
Retaining agonistic activity at the glycine coagonist site of the NMDA receptor in molecules derived from glycine or d-serine has proven to be difficult because in the vicinity of the alpha-amino acid group little substitution is tolerated. We have solved

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