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34371-14-7, 2-Deoxy-D-ribonic acid-1,4-lactone, CAS:34371-14-7

34371-14-7 ,2-Deoxy-D-ribonic acid-1,4-lactone,
CAS:34371-14-7
C5H8O4 / 132.12
MFCD15144952

2-Deoxy-D-ribonic acid-1,4-lactone

2-脱氧-D-核糖酸-1,4-内酯

2-Deoxy-D-ribonic acid-1,4-lactone (2DRA) is a chemical compound with physiological effects. 2DRA is an irreversible inhibitor of DNA polymerase that has been shown to be a potent inhibitor of nuclear DNA synthesis in vitro and in vivo. The 2DRA inhibits the transfer reactions that are required for the replication of DNA. 2DRA binds to the nuclease domain of the enzyme and prevents it from cutting the phosphodiester bonds, leading to inhibition of DNA synthesis. This compound also has genotoxic effects and can cause mutation in cells through radiation or chemical treatment.

(4S,5R)-4-hydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one is a complex organic compound that has been the focus of several scientific research studies. It is a five-membered cyclic molecule of sugars classified as a furanone derivative.

Definition and Background:

(4S,5R)-4-hydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one is minimally soluble in water and has a melting point of 197 degrees Celsius. It is an intermediate chemical compound in the synthesis of natural products such as C-ribosylated-isoflavones and teicoplanin. Additionally, it is a naturally-occurring metabolite in bacteria and yeast, acting as a quorum-sensing signaling molecule.

Physical and Chemical Properties:

(4S,5R)-4-hydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one is a stable, white crystalline solid with a molecular weight of 132.11 g/mol. The compound is polar and has a high boiling point, which makes it difficult to work with at room temperature.

Synthesis and Characterization:

The synthesis of (4S,5R)-4-hydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one can be done through different methods, such as acid-promoted cyclization of alkoxy aldehydes, deoxydehydration or acid-catalyzed dehydration. Its characterization is typically carried out by spectroscopic and chromatographic methods such as nuclear magnetic resonance spectroscopy (NMR), mass spectrometry, and gas chromatography-mass spectrometry (GC-MS).

Analytical Methods:

Analytical methods that have been used to determine the presence and concentration of (4S,5R)-4-hydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one include high-performance liquid chromatography (HPLC) and capillary electrophoresis.

Biological Properties:

(4S,5R)-4-hydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one has been shown to have antibacterial and antifungal properties, making it useful in the development of new antibiotics. Additionally, it has been found to play a role in microbial communication and biofilm formation. Currently, researchers are exploring its potential role as an anti-tumor agent.

Toxicity and Safety in Scientific Experiments:

The toxicity of (4S,5R)-4-hydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one has not been extensively studied. However, it has been shown to have low toxicity levels in laboratory experiments.

Applications in Scientific Experiments:

(4S,5R)-4-hydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one has been used in scientific experiments as a quorum-sensing agent, as a natural insecticide and fungicide, and as a building block in the synthesis of various organic compounds.

Current State of Research:

Recent research has focused on the role of (4S,5R)-4-hydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one in quorum sensing, biofilm formation, and as a precursor to the synthesis of antibiotics, such as teicoplanin.

Potential Implications in Various Fields of Research and Industry:

(4S,5R)-4-hydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one has potential implications in the fields of synthetic chemistry, drug discovery, and microbiology.

Limitations and Future Directions:

One limitation of (4S,5R)-4-hydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one is its low solubility in water, which limits its application in certain fields. Future research should focus on the development of more efficient synthesis methods that allow for larger-scale production of the compound. Additionally, further studies are needed to fully understand the biological properties and potential applications of this complex organic compound.

List of Future Directions:

1. Developing more efficient synthesis methods for (4S,5R)-4-hydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one to allow for larger-scale production.

2. Exploring the potential applications of this compound in the field of drug discovery, particularly in the development of new antibiotics.

3. Investigating the role of (4S,5R)-4-hydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one in the formation of biofilms and its potential use as a quorum-sensing agent.

4. Examining the toxicity levels of this compound in laboratory experiments.

5. Studying the potential use of (4S,5R)-4-hydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one as an anti-tumor agent.

6. Investigating the potential role of this compound in the development of new insecticides and fungicides.

7. Exploring the use of this compound as a building block in the synthesis of other organic compounds.

8. Assessing the potential implications of (4S,5R)-4-hydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one in broader areas of research, such as materials science and nanotechnology.

9. Investigating the impact of this compound on the environment in areas where it has been used as an insecticide or fungicide.

10. Studying the potential applications of (4S,5R)-4-hydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one in other areas of biology, such as neuroscience and biochemistry.

CAS Number34371-14-7
Product Name(4S,5R)-4-hydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one
IUPAC Name(4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-one
Molecular FormulaC5H8O4
Molecular Weight132.11 g/mol
InChIInChI=1S/C5H8O4/c6-2-4-3(7)1-5(8)9-4/h3-4,6-7H,1-2H2/t3-,4+/m0/s1
InChI KeyYIXDEYPPAGPYDP-IUYQGCFVSA-N
SMILESC1C(C(OC1=O)CO)O
Synonyms2,4,5-TP, 2,4,5-trihydroxypentanoic acid gamma-lactone, 2-deoxy-ribono-1,4-lactone, 2-deoxyribonolactone
Canonical SMILESC1C(C(OC1=O)CO)O
Isomeric SMILESC1[C@@H]([C@H](OC1=O)CO)O
CAS No: 34371-14-7 MDL No: MFCD15144952 Chemical Formula: C5H8O4 Molecular Weight: 132.11
References: 1. Ortuno RM, et.al.,, Tetrahydron, 1993, 49, 2, p349


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