Biotin pentafluorophenyl ester
[CAS# 120550-35-8]

Identification

• Classification: Organic raw materials >> Organic fluorine compound >> Fluorophenol series
• Name: Biotin pentafluorophenyl ester
• Synonyms: (3aS,4S,6aR)-Hexahydro-2-oxo-1H-thieno[3,4-d]imidazole-4-pentanoicacid 2,3,4,5,6-pentafluorophenyl ester
• Molecular Formula: C₁₆H₁₅F₅N₂O₃S
• Molecular Weight: 410.36
• CAS Registry Number: 120550-35-8
• SMILES: C1[C@H]2[C@@H]([C@@H](S1)CCCCC(=O)OC3=C(C(=C(C(=C3F)F)F)F)F)NC(=O)N2

Properties

• Density: 1.4±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.513, Calc.^*
• Boiling Point: 555.3±50.0 °C (760 mmHg), Calc.^*
• Flash Point: 289.6±30.1 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Discovery and Applications

Biotin pentafluorophenyl ester is an ester derivative of biotin, which is a water-soluble B-vitamin also known as vitamin H or vitamin B7. Biotin plays an essential role in cellular metabolism, as it is involved in several carboxylation reactions that are important for the synthesis of fatty acids, the metabolism of amino acids, and gluconeogenesis. Biotin and its derivatives have been extensively studied due to their biological significance, and various chemical modifications have been developed to enhance their utility in different applications.

The chemical modification of biotin to form its ester derivative, biotin pentafluorophenyl ester, involves the esterification of biotin with pentafluorophenol. This modification is designed to improve the chemical reactivity of biotin, allowing for easier conjugation to other molecules. The pentafluorophenyl group in this ester derivative serves as a reactive handle, enabling the biotin molecule to be linked to various biomolecules, polymers, or materials through reactions that are facilitated by the ester group. The pentafluorophenyl group itself is a strong electron-withdrawing group, which enhances the reactivity of the ester bond, making the compound useful for coupling reactions.

One of the main applications of biotin pentafluorophenyl ester is in bioconjugation techniques. Biotin is well-known for its strong affinity for streptavidin, a protein that binds to biotin with extremely high specificity and affinity. This property is utilized in a variety of laboratory and clinical applications. The introduction of the pentafluorophenyl ester group improves the ability to attach biotin to other molecules in a controlled and efficient manner. Biotinylation reactions, where biotin is covalently linked to proteins, nucleic acids, or other biomolecules, are widely used in biochemical assays, immunoassays, and proteomics.

The pentafluorophenyl ester of biotin can also be employed in the creation of biotinylated polymers, which can be used in applications such as drug delivery, diagnostics, and biosensor development. For example, biotinylated surfaces can be used in biosensors where the biotin-streptavidin interaction is used to capture target molecules or facilitate detection. The high reactivity of biotin pentafluorophenyl ester allows for more efficient conjugation to these surfaces or materials.

Additionally, biotin pentafluorophenyl ester has potential use in the synthesis of targeted therapeutics. By attaching biotin to specific drugs or therapeutic agents through the ester group, targeted delivery to cells expressing streptavidin or biotin-binding proteins can be achieved. This approach can enhance the specificity and effectiveness of treatments, particularly in the case of cancer therapy or other diseases where targeted delivery is beneficial.

Biotin pentafluorophenyl ester also finds utility in molecular imaging and diagnostics. The ability to conjugate biotin to imaging agents or probes makes it possible to target specific tissues or cells, enabling more precise imaging and diagnostic capabilities. The high binding affinity between biotin and streptavidin is utilized in techniques such as immunohistochemistry, fluorescence microscopy, and in vivo imaging.

Safety considerations for handling biotin pentafluorophenyl ester are similar to those for other ester compounds. It should be handled with care, especially considering the potential reactivity of the pentafluorophenyl ester group. Proper laboratory safety protocols should be followed, including the use of personal protective equipment such as gloves, goggles, and lab coats. The compound should be stored in a cool, dry place, away from sources of moisture or excessive heat, which could potentially lead to hydrolysis of the ester bond.

In conclusion, biotin pentafluorophenyl ester is a useful chemical derivative of biotin with enhanced reactivity that finds applications in bioconjugation, molecular imaging, diagnostics, and targeted drug delivery. Its ability to efficiently link biotin to various biomolecules and materials makes it an important tool in a wide range of biochemical and medical research applications. The chemical structure and properties of this ester derivative facilitate its use in the development of advanced diagnostic and therapeutic strategies.

References

2016. Effective and safe laser action in the surface fusion of a ternary medium while preserving the functionality of the easily fusible component. Bulletin of the Russian Academy of Sciences: Physics, 80(8).
DOI: 10.3103/s1062873816080037