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D9378

Sigma-Aldrich

3,4-Dihydroxy-D-phenylalanine

≥95% (TLC), powder, DOPA enantiomer

Synonym(s):

3-(3,4-Dihydroxyphenyl)-D-alanine, D-3-Hydroxytyrosine, D-DOPA

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About This Item

Empirical Formula (Hill Notation):
C9H11NO4
CAS Number:
Molecular Weight:
197.19
Beilstein:
2417637
EC Number:
MDL number:
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.32

product name

3,4-Dihydroxy-D-phenylalanine, powder, ≥95%

Assay

≥95%

form

powder

mp

276-278 °C (lit.)

solubility

1 M HCl: soluble
ethanol: insoluble

storage temp.

−20°C

SMILES string

N[C@H](Cc1ccc(O)c(O)c1)C(O)=O

InChI

1S/C9H11NO4/c10-6(9(13)14)3-5-1-2-7(11)8(12)4-5/h1-2,4,6,11-12H,3,10H2,(H,13,14)/t6-/m1/s1

InChI key

WTDRDQBEARUVNC-ZCFIWIBFSA-N

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Application

3,4-Dihydroxy-D-phenylalanine has been used as a standard in high-performance liquid chromatography (HPLC) analysis of L-DOPA extracted from both germinated and raw seed flours of velvet bean.

Biochem/physiol Actions

3,4-Dihydroxy-D-phenylalanine (D-DOPA) is a DOPA enantiomer. It exhibits antimicrobial activity. D-DOPA serves as a precursor for dopamine.

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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Tomoya Kawazoe et al.
Chemical record (New York, N.Y.), 7(5), 305-315 (2007-10-10)
The flavoprotein D-amino acid oxidase (DAO) degrades the gliotransmitter D-Ser, a potent activator of N-methyl-D-aspartate-type glutamate receptors. A body of evidence suggests that DAO, together with its activator, G72 protein, may play a key role in the pathophysiology of schizophrenia.
Nan Lu et al.
Electrophoresis (2020-09-20)
This review summarizes recent developments (over the past decade) in the field of microfluidics-based solutions for enantiomeric separation and detection. The progress in various formats of microchip electrodriven separations, such as MCE, microchip electrochromatography, and multidimensional separation techniques, is discussed.
Mark H Burrell et al.
ACS chemical neuroscience, 6(11), 1802-1812 (2015-09-01)
Tonic dopamine (DA) levels influence the activity of dopaminergic neurons and the dynamics of fast dopaminergic transmission. Although carbon fiber microelectrodes and fast-scan cyclic voltammetry (FSCV) have been extensively used to quantify stimulus-induced release and uptake of DA in vivo
Anthony Bertucci et al.
Bioorganic & medicinal chemistry, 18(6), 2300-2303 (2010-02-24)
The activity of the coral Stylophora pystillata secretory carbonic anhydrase STPCA has been tested in presence of amino acids and amines. All the investigated compounds showed a positive, activating effect on k(cat) and have been separated in weak (K(A) in
Daniela Vullo et al.
Bioorganic & medicinal chemistry letters, 17(15), 4107-4112 (2007-06-02)
An activation study of the human carbonic anhydrase (hCA, EC 4.2.1.1) isozymes VII and XIV using a small library of natural/non-natural amino acids and aromatic/heterocyclic amines is reported. hCA VII was efficiently activated by L-/D-His, dopamine and serotonin (K(A)s of

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