DMOG

DMOG Basic information

Product Name:

Synonyms:

N-(METHOXYOXOACETYL)-GLYCINE METHYL ESTER;DIMETHYLOXALLYL GLYCINE;HIF-Hydroxylase Inhibitor, DMOG - CAS 89464-63-1 - Calbiochem;DIMETHYLOXALYLGLYCINE;DMOG;Dimethyloxaloylglycine;N-[(Methoxycarbonyl)Methyl]oxaMic Acid Methyl Ester;DiMethyloxaloylglycine (DMOG)

CAS:

MF:

C6H9NO5

MW:

175.14

EINECS:

 

Product Categories:

Bio-material;NONE;Other;Amino Acids 13C, 2H, 15N;Amino Acids & Derivatives;Inhibitors

Mol File:

 

DMOG Chemical Properties

Melting point 

46-48°C

storage temp. 

Refrigerator

solubility 

H2O: >30mg/mL

form 

Solid

color 

white to off-white

Water Solubility 

Soluble in water at 30mg/ml.

 

Safety Information

Hazard Codes 

Risk Statements 

WGK Germany 

3

HazardClass 

IRRITANT

MSDS Information

 

DMOG Usage And Synthesis

Chemical Properties

Off-White to Pale Pink Solid

Uses

DMOG is a cell permeable prolyl-4-hydroxylase inhibitor which upregulates HIF activity. HIF activation stimulates angiogenesis in several different models (1nM). DMOG also inhibits FIH (factor inhibiting HIF), an asparaginyl hydroxylase, which enhances the HIF response. It is active in vivo and attenuates myocardial injury in a rabbit ischemia reperfusion model (20mg/Kg).

Enzyme inhibitor

This iron-binding a-ketoglutarate (2-oxoglutarate) analogue (FW = 147.09 g/mol; also named N-oxaloglycine) competitively inhibits prolyl-4- hydroxylase (Reaction: Procollagen (L-proline) + a-ketoglutarate + O2 → Procollagen ( (2S,4R) -4-hydroxyproline) + succinate + CO2). During catalysis, prolyl-4-hydroxylase forms Fe (III), and the latter most likely makes an extremely stable metal ion complex with N-oxaloglycine. Substitution on the glycine moiety alters inhibitor activity stereoselectively and that, if the w-carboxylate is homologated or replaced, either by acylsulfonamides or anilide, activity is likewise sharply reduced. Prolyl- 4-Hydroxylase Catalysis: Each catalytic round of this posttranslational modifying enzyme reaction occurs in two stages. O2 is bound end-on in an axial position, producing a dioxygen unit. Nucleophilic attack at C-2 generates a tetrahedral intermediate, with loss of the double bond in dioxygen and bonds to iron and the a-carbon of a-ketoglutarate. Elimination of CO2 coincides with formation of the Fe (IV) =O species. The second stage involves the abstraction of the pro-R hydrogen atom from C-4 of proline, followed by radical combination, yielding hydroxyproline. In the presence of a-ketoglutarate, enzyme-bound Fe2+ is rapidly converted to Fe3+, resulting in inactivation of the enzyme Ascorbate is utilized as a cofactor to reduce Fe (III) back to Fe (II). Cell-Permeable Analogue: Dimethyloxalylglycine (FW = 175.14 g/mol; CAS 89464-63-1; Symbol: DMOG, also named N- (methoxyoxoacetyl) -glycine methyl ester) is metabolicaly demethylated to form N-oxaloglycine upon entry to many cells.

 

DMOG Preparation Products And Raw materials