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H2380

Sigma-Aldrich

6-Hydroxy-DL-DOPA

≥98% (HPLC), powder, APE1 inhibitor

Synonym(s):

2,4,5-Trihydroxy-DL-phenylalanine, 2,5-Dihydroxy-DL-tyrosine

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About This Item

Empirical Formula (Hill Notation):
C9H11NO5
CAS Number:
21373-30-8
Molecular Weight:
213.19
Beilstein:
2860065
MDL number:
MFCD00004272
UNSPSC Code:
12352200
PubChem Substance ID:
24278464
NACRES:
NA.32

product name

6-Hydroxy-DL-DOPA, ≥98% (HPLC), powder

Quality Level

200

Assay

≥98% (HPLC)

form

powder

color

off-white

solubility

H2O: 3 mg/mL
1 M HCl: 50 mg/mL (Solutions should be freshly prepared and protected from exposure to light.)

storage temp.

−20°C

SMILES string

NC(Cc1cc(O)c(O)cc1O)C(O)=O

InChI

1S/C9H11NO5/c10-5(9(14)15)1-4-2-7(12)8(13)3-6(4)11/h2-3,5,11-13H,1,10H2,(H,14,15)

InChI key

YLKRUSPZOTYMAT-UHFFFAOYSA-N

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General description

Dissolve in oxygen-free boiled water containing 0.1% sodium metabisulfite or other antioxidant. Solutions should be freshly prepared and protected from exposure to light.

Biochem/physiol Actions

6-Hydroxy-DL-DOPA is an inhibitor of APE1 (apurinic/apyrimidinic endonuclease) repair-function activity. APE1 is a nuclease crucial for DNA base excision repair pathway. 6-Hydroxy-DL-DOPA also blocks RAD52 (DNA repair protein) single-stranded DNA binding domain.
Precursor of the catecholaminergic neurotoxin, 6-hydroxydopamine; converted to 6-hydroxydopamine by L-aromatic amino acid decarboxylase.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Caution

Hygroscopic; photosensitive

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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Gurushankar Chandramouly et al.
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Suppression of RAD52 causes synthetic lethality in BRCA-deficient cells. Yet pharmacological inhibition of RAD52, which binds single-strand DNA (ssDNA) and lacks enzymatic activity, has not been demonstrated. Here, we identify the small molecule 6-hydroxy-DL-dopa (6-OH-dopa) as a major allosteric inhibitor
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