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4-Thiouracil

(Synonyms: 4-硫尿嘧啶) 目录号 : GC40477

A photoreactive nucleobase analog

4-Thiouracil Chemical Structure

Cas No.:591-28-6

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500mg
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产品描述

4-Thiouracil is a site-specific, photoactivatable probe used to detect RNA structures and nucleic acid-nucleic acid contacts. It absorbs ultraviolet light >300 nm and, in the presence of oxygen, acts as an energy donor to produce singlet oxygen by triplet-triplet energy transfer. The highly reactive oxygen species then reacts readily with 4-thiouracil, leading to the production of uracil and uracil-6-sulfonate, which is fluorescent at a wavelength of ~390 nm. 4-Thiouracil is used as a T. gondii uracil phosphoribosyltransferase substrate to produce 4-thiouridine monophosphate, which can ultimately be incorporated into RNA.

Chemical Properties

Cas No. 591-28-6 SDF
别名 4-硫尿嘧啶
Canonical SMILES O=C(NC=C1)NC1=S
分子式 C4H4N2OS 分子量 128.1
溶解度 DMF: 12 mg/mL,DMF:PBS (pH 7.2) (1:5): 0.5 mg/mL,DMSO: 10 mg/mL,Ethanol: 2 mg/mL 储存条件 Store at -20°C, protect from light
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1 mM 7.8064 mL 39.032 mL 78.064 mL
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10 mM 0.7806 mL 3.9032 mL 7.8064 mL
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Research Update

Structural Evidence for a [4Fe-5S] Intermediate in the Non-Redox Desulfuration of Thiouracil

Angew Chem Int Ed Engl 2021 Jan 4;60(1):424-431.PMID:32929873DOI:10.1002/anie.202011211.

We recently discovered a [Fe-S]-containing protein with in vivo thiouracil desulfidase activity, dubbed TudS. The crystal structure of TudS refined at 1.5 Å resolution is reported; it harbors a [4Fe-4S] cluster bound by three cysteines only. Incubation of TudS crystals with 4-Thiouracil trapped the cluster with a hydrosulfide ligand bound to the fourth non-protein-bonded iron, as established by the sulfur anomalous signal. This indicates that a [4Fe-5S] state of the cluster is a catalytic intermediate in the desulfuration reaction. Structural data and site-directed mutagenesis indicate that a water molecule is located next to the hydrosulfide ligand and to two catalytically important residues, Ser101 and Glu45. This information, together with modeling studies allow us to propose a mechanism for the unprecedented non-redox enzymatic desulfuration of thiouracil, in which a [4Fe-4S] cluster binds and activates the sulfur atom of the substrate.

Non-radioactive In Vivo Labeling of RNA with 4-Thiouracil

Methods Mol Biol 2022;2533:199-213.PMID:35796990DOI:10.1007/978-1-0716-2501-9_12.

RNA molecules and their expression dynamics play essential roles in the establishment of complex cellular phenotypes and/or in the rapid cellular adaption to environmental changes. Accordingly, analyzing RNA expression remains an important step to understand the molecular basis controlling the formation of cellular phenotypes, cellular homeostasis or disease progression. Steady-state RNA levels in the cells are controlled by the sum of highly dynamic molecular processes contributing to RNA expression and can be classified in transcription, maturation and degradation. The main goal of analyzing RNA dynamics is to disentangle the individual contribution of these molecular processes to the life cycle of a given RNA under different physiological conditions. In the recent years, the use of nonradioactive nucleotide/nucleoside analogs and improved chemistry, in combination with time-dependent and high-throughput analysis, have greatly expanded our understanding of RNA metabolism across various cell types, organisms, and growth conditions.In this chapter, we describe a step-by-step protocol allowing pulse labeling of RNA with the nonradioactive nucleotide analog, 4-Thiouracil , in the eukaryotic model organism Saccharomyces cerevisiae and the model archaeon Haloferax volcanii .

Photoelectron spectra of 2-thiouracil, 4-Thiouracil, and 2,4-dithiouracil

J Chem Phys 2016 Feb 21;144(7):074303.PMID:26896982DOI:10.1063/1.4941948.

Ground- and excited-state UV photoelectron spectra of thiouracils (2-thiouracil, 4-Thiouracil, and 2,4-dithiouracil) have been simulated using multireference configuration interaction calculations and Dyson norms as a measure for the photoionization intensity. Except for a constant shift, the calculated spectrum of 2-thiouracil agrees very well with experiment, while no experimental spectra are available for the two other compounds. For all three molecules, the photoelectron spectra show distinct bands due to ionization of the sulphur and oxygen lone pairs and the pyrimidine π system. The excited-state photoelectron spectra of 2-thiouracil show bands at much lower energies than in the ground state spectrum, allowing to monitor the excited-state population in time-resolved UV photoelectron spectroscopy experiments. However, the results also reveal that single-photon ionization probe schemes alone will not allow monitoring all photodynamic processes existing in 2-thiouracil. Especially, due to overlapping bands of singlet and triplet states the clear observation of intersystem crossing will be hampered.

Biomolecules of 2-Thiouracil, 4-Thiouracil and 2,4-Dithiouracil: A DFT Study of the Hydration, Molecular Docking and Effect in DNA:RNAMicrohelixes

Int J Mol Sci 2019 Jul 15;20(14):3477.PMID:31311161DOI:10.3390/ijms20143477.

The molecular structure of 2-thiouracil, 4-Thiouracil and 2,4-dithiouracil was analyzed under the effect of the first and second hydration shell by using the B3LYP density functional (DFT) method, and the results were compared to those obtained for the uracil molecule. A slight difference in the water distribution appears in these molecules. On the hydration of these molecules several trends in bond lengths and atomic charges were established. The ring in uracil molecule appears easier to be deformed and adapted to different environments as compared to that when it is thio-substituted. Molecular docking calculations of 2-thiouracil against three different pathogens: Bacillus subtilis, Escherichia coli and Candida albicans were carried out. Docking calculations of 2,4-dithiouracil ligand with various targeted proteins were also performed. Different DNA: RNA hybrid microhelixes with uridine, 2-thiouridine, 4-thiouridine and 2,4-dithiouridine nucleosides were optimized in a simple model with three nucleotide base pairs. Two main types of microhelixes were analyzed in detail depending on the intramolecular H-bond of the 2'-OH group. The weaker Watson-Crick (WC) base pair formed with thio-substituted uracil than with unsubstituted ones slightly deforms the helical and backbone parameters, especially with 2,4-dithiouridine. However, the thio-substitution significantly increases the dipole moment of the A-type microhelixes, as well as the rise and propeller twist parameters.

Time-Resolved Optical Pump-Resonant X-ray Probe Spectroscopy of 4-Thiouracil: A Simulation Study

J Chem Theory Comput 2022 May 10;18(5):3075-3088.PMID:35476905DOI:10.1021/acs.jctc.2c00064.

We theoretically monitor the photoinduced ππ* → nπ* internal conversion process in 4-Thiouracil (4TU), triggered by an optical pump. The element-sensitive spectroscopic signatures are recorded by a resonant X-ray probe tuned to the sulfur, oxygen, or nitrogen K-edge. We employ high-level electronic structure methods optimized for core-excited electronic structure calculation combined with quantum nuclear wavepacket dynamics computed on two relevant nuclear modes, fully accounting for their quantum nature of nuclear motions. We critically discuss the capabilities and limitations of the resonant technique. For sulfur and nitrogen, we document a pre-edge spectral window free from ground-state background and rich with ππ* and nπ* absorption features. The lowest sulfur K-edge shows strong absorption for both ππ* and nπ*. In the lowest nitrogen K-edge window, we resolve a state-specific fingerprint of the ππ* and an approximate timing of the conical intersection via its depletion. A spectral signature of the nπ* transition, not accessible by UV-vis spectroscopy, is identified. The oxygen K-edge is not sensitive to molecular deformations and gives steady transient absorption features without spectral dynamics. The ππ*/nπ* coherence information is masked by more intense contributions from populations. Altogether, element-specific time-resolved resonant X-ray spectroscopy provides a detailed picture of the electronic excited-state dynamics and therefore a sensitive window into the photophysics of thiobases.