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SML1874

Sigma-Aldrich

DM-NOFD

≥98% (HPLC)

Synonym(s):

Dimethyl N-oxalyl-D-phenylalanine, N-(2-Methoxy-2-oxoacetyl)-D-phenylalanine methyl ester, N-Oxalyl-D-phenylalanine dimethyl ester

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About This Item

Empirical Formula (Hill Notation):
C13H15NO5
CAS Number:
865488-53-5
Molecular Weight:
265.26
UNSPSC Code:
12352200
NACRES:
NA.77
Pricing and availability is not currently available.

Quality Level

100

Assay

≥98% (HPLC)

form

oil

color

, colorless to dark yellow

storage temp.

2-8°C

SMILES string

O=C(C(N[C@H](CC1=CC=CC=C1)C(OC)=O)=O)OC

InChI

1S/C13H15NO5/c1-18-12(16)10(14-11(15)13(17)19-2)8-9-6-4-3-5-7-9/h3-7,10H,8H2,1-2H3,(H,14,15)/t10-/m1/s1

InChI key

CAUUPQLNYYFMOQ-SNVBAGLBSA-N

General description

Dimethyl N-oxalyl-D-phenylalanine (DM-NOFD) is a small FIH (factor-inhibiting) inhibitor molecule.[1]

Biochem/physiol Actions

DM-NOFD is a cell penetrant, prodrug of NOFD a potent and selective inhibitor of an asparaginyl hydroxylase FIH (factor-inhibiting HIF).
DM-NOFD is a cell penetrant, prodrug of NOFD a potent and selective inhibitor of an asparaginyl hydroxylase FIH (factor-inhibiting HIF). DM-NOFD efficiently reduces HIF1a CAD (C-terminal activating domain) hydroxylation in MCF-7 cells.

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
017M4624V

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Tuning the transcriptional response to hypoxia by inhibiting HIF prolyl-and asparaginyl-hydroxylases.
Chan MC, et al.
The Journal of Biological Chemistry, jbc-M116 (2016)
Michael A McDonough et al.
Journal of the American Chemical Society, 127(21), 7680-7681 (2005-05-26)
A set of four non-heme iron(II) and 2-oxoglutarate-dependent enzymes catalyze the post-translational modification of a transcription factor, hypoxia inducible factor (HIF), that mediates the hypoxic response in animals. Hydroxylation of HIF both causes its degradation and limits its activity. We
Mun Chiang Chan et al.
The Journal of biological chemistry, 291(39), 20661-20673 (2016-08-10)
The hypoxia-inducible factor (HIF) system orchestrates cellular responses to hypoxia in animals. HIF is an α/β-heterodimeric transcription factor that regulates the expression of hundreds of genes in a tissue context-dependent manner. The major hypoxia-sensing component of the HIF system involves

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