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D7628

Sigma-Aldrich

Dihydrouracil

powder

Synonym(e):

5,6-Dihydro-2,4-dihydroxypyrimidine

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About This Item

Empirische Formel (Hill-System):
C4H6N2O2
CAS-Nummer:
504-07-4
Molekulargewicht:
114.10
EG-Nummer:
207-982-1
MDL-Nummer:
MFCD00006029
UNSPSC-Code:
12352005
PubChem Substanz-ID:
24894143
NACRES:
NA.21

Form

powder

mp (Schmelzpunkt)

279-281 °C (lit.)

SMILES String

O=C1CCNC(=O)N1

InChI

1S/C4H6N2O2/c7-3-1-2-5-4(8)6-3/h1-2H2,(H2,5,6,7,8)

InChIKey

OIVLITBTBDPEFK-UHFFFAOYSA-N

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Allgemeine Beschreibung

Dihydrouracil (DiHU) is a minor base found in transfer ribonucleic acid (tRNA). It is similar to uracil with the only exception that the C5-C6 bond is saturated. It crystallized in the monoclinic system with space group P21/C. Its crystalline structure has been analyzed. Its generation from L-cysteine and uracil via photochemical addition has been described.

Anwendung

Dihydrouracil has been used as a standard for ureido group in the colorimentric assay of transfer ribonucleic acid (tRNA).

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)

Analysenzertifikate (COA)

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L-Dihydroorotsäure ≥99%

Sigma-Aldrich

D7128

L-Dihydroorotsäure

Thymin ≥99%

Sigma-Aldrich

T0376

Thymin

N-Acetyl-L-asparaginsäure ≥99.0% (T)

Sigma-Aldrich

00920

N-Acetyl-L-asparaginsäure

Purin 98%

Sigma-Aldrich

P55805

Purin

Jihane Basbous et al.
Nucleic acids research, 48(4), 1886-1904 (2019-12-20)
Imbalance in the level of the pyrimidine degradation products dihydrouracil and dihydrothymine is associated with cellular transformation and cancer progression. Dihydropyrimidines are degraded by dihydropyrimidinase (DHP), a zinc metalloenzyme that is upregulated in solid tumors but not in the corresponding
Stereochemistry of nucleic acids and their constituents. VI. The crystal structure and conformation of dihydrouracil: a minor base of transfer-ribonucleic acid.
Rohrer DC and Sundaralingam M.
Acta Crystallographica Section B, Structural Science, 26(5), 546-553 (1970)
Ryota Hidese et al.
Journal of bacteriology, 193(4), 989-993 (2010-12-21)
The reductive pyrimidine catabolic pathway is absent in Escherichia coli. However, the bacterium contains an enzyme homologous to mammalian dihydropyrimidine dehydrogenase. Here, we show that E. coli dihydropyrimidine dehydrogenase is the first member of a novel NADH-dependent subclass of iron-sulfur
Futao Yu et al.
Proceedings of the National Academy of Sciences of the United States of America, 108(49), 19593-19598 (2011-11-30)
Dihydrouridine (D) is a highly conserved modified base found in tRNAs from all domains of life. Dihydrouridine synthase (Dus) catalyzes the D formation of tRNA through reduction of uracil base with flavin mononucleotide (FMN) as a cofactor. Here, we report
Sylke Schneider et al.
Journal of the American College of Surgeons, 200(3), 336-344 (2005-03-02)
To find out if neoadjuvant therapy could alter tumor response determinants that might affect tumor sensitivity to the treatment, we investigated intratumoral expressions of genes associated with chemosensitivity, radiosensitivity, or both before and after radiochemotherapy. Twenty-four patients with locally advanced
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