D7128

L-Dihydroorotsäure

Name: <SC>L</SC>-Dihydroorotsäure
Brand: SIGMA
Price: 170 EUR

≥99%

Synonym(e):

2,6-Dioxohexahydro-4-pyrimidinecarboxylic acid, L-Hydroorotic acid, Dihydro-L-orotic acid

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Über diesen Artikel

Empirische Formel (Hill-System):

C₅H₆N₂O₄

CAS-Nummer:

5988-19-2

Molekulargewicht:

158.11

NACRES:

NA.83

PubChem Substance ID:

24894080

UNSPSC Code:

12352204

MDL number:

MFCD00085339

Assay:

≥99%

Form:

powder

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Unterstützung erhalten

InChI

1S/C5H6N2O4/c8-3-1-2(4(9)10)6-5(11)7-3/h2H,1H2,(H,9,10)(H2,6,7,8,11)/t2-/m0/s1

SMILES string

OC(=O)[C@@H]1CC(=O)NC(=O)N1

InChI key

UFIVEPVSAGBUSI-REOHCLBHSA-N

assay

≥99%

form

powder

mp

254-255 °C (dec.) (lit.)

Quality Level

200

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Dieser Artikel	537306	O8402	H9633
Sigma-Aldrich D7128 L-Dihydroorotic acid	Sigma-Aldrich 537306 D-Hydroorotic acid	Sigma-Aldrich O8402 Orotic acid monohydrate	Sigma-Aldrich H9633 L-Homocysteic acid
assay ≥99%	assay 98%	assay 97%	assay ≥95%, ≥98% (TLC)
Quality Level 200	Quality Level 100	Quality Level 200	Quality Level 200
form powder	form -	form powder	form powder
mp 254-255 °C (dec.) (lit.)	mp 255 °C (dec.) (lit.)	mp >300 °C (lit.)	mp -

Application

L-Dihydroorotic acid has been used as a substrate in dihydroorotate dehydrogenase (DHODH) assay.[1][2][3]

Biochem/physiol Actions

L-Dihydroorotic acid (DHO) serves as a substrate for dihydroorotate dehydrogenase (DHODH), an enzyme in the de novo synthesis of pyrimidine. Inhibition of DHOH by its inhibitors causes a large accumulation of upstream metabolite DHO and a reduction in the uridine levels. Therefore, DHO and uridine can be used as biomarkers for pyrimidine synthesis for the clinical development of DHOH inhibitors.[4]

pictograms

GHS07

signalword

Warning

hcodes

H315,H319,H335

pcodes

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Lagerklasse

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Quantitation of uridine and L-dihydroorotic acid in human plasma by LC-MS/MS using a surrogate matrix approach.

Feng Yin et al.

Journal of pharmaceutical and biomedical analysis, 192, 113669-113669 (2020-10-30)

Uridine and L-dihydroorotate (DHO) are important intermediates of de novo as well as salvage pathways for the biosynthesis of pyrimidines, which are the building blocks of nucleic acids - DNA and RNA. These metabolites are known to be significant biomarkers

Isolation of mitochondria from Plasmodium falciparum showing dihydroorotate dependent respiration.

E Takashima et al.

Parasitology international, 50(4), 273-278 (2001-11-24)

Using N2 cavitation, we established a protocol to prepare the active mitochondria from Plasmodium falciparum showing a higher succinate dehydrogenase activity than previously reported and a dihydroorotate-dependent respiration. The fact that fumarate partially inhibited the dihydroorotate dependent respiration suggests that

13C and 15N isotope effects for conversion of L-dihydroorotate to N-carbamyl-L-aspartate using dihydroorotase from hamster and Bacillus caldolyticus.

Mark A Anderson et al.

Biochemistry, 45(23), 7132-7139 (2006-06-07)

In the pyrimidine biosynthetic pathway, N-carbamyl-L-aspartate (CA-asp) is converted to L-dihydroorotate (DHO) by dihydroorotase (DHOase). The mechanism of this important reaction was probed using primary and secondary 15N and 13C isotope effects on the ring opening of DHO using isotope

Kinetic mechanism and catalysis of Trypanosoma cruzi dihydroorotate dehydrogenase enzyme evaluated by isothermal titration calorimetry.

Juliana Cheleski et al.

Analytical biochemistry, 399(1), 13-22 (2009-11-26)

Trypanosoma cruzi dihydroorotate dehydrogenase (TcDHODH) catalyzes the oxidation of l-dihydroorotate to orotate with concomitant reduction of fumarate to succinate in the de novo pyrimidine biosynthetic pathway. Based on the important need to characterize catalytic mechanism of TcDHODH, we have tailored

The zebrafish orthologue of the human hepatocerebral disease gene MPV17 plays pleiotropic roles in mitochondria.

Laura Martorano et al.

Disease models & mechanisms, 12(3) (2019-03-06)

Mitochondrial DNA depletion syndromes (MDS) are a group of rare autosomal recessive disorders with early onset and no cure available. MDS are caused by mutations in nuclear genes involved in mitochondrial DNA (mtDNA) maintenance, and characterized by both a strong

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L-Dihydroorotsäure