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Fmoc-D-proline is a crucial non-natural amino acid derivative used in modern solid-phase peptide synthesis. Its molecular structure ingeniously combines the unique right-handed helical conformation of D-proline with the protection strategy of fluorene methoxycarbonyl: D-proline, as the mirror isomer of proline, has the inherent rigid pyrrolidine ring that can induce the reverse conformation of the peptide chain, effectively enhancing the stability of peptide molecules against protease degradation, and endowing it with specific biological activity different from the natural L-type; while the top Fmoc protecting group, with its excellent controllable acidity and alkalinity properties, can be efficiently removed under mild alkaline conditions, and its inherent strong ultraviolet absorption property provides convenience for real-time monitoring of the synthesis process. This combination makes Fmoc-D-proline a core building block for constructing novel-targeting peptides, receptor antagonists, and conformationally restricted mimics, particularly demonstrating irreplaceable value in the development of novel chiral catalysts and functional materials with unique spatial folding, effectively promoting the cross-development of asymmetric synthesis and peptidopharmacology.
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Chemical Formula |
C20H19NO4 |
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Exact Mass |
337 |
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Molecular Weight |
337 |
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m/z |
337 (100.0%), 338 (21.6%), 339 (2.2%) |
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Elemental Analysis |
C, 71.20; H, 5.68; N, 4.15; O, 18.97 |
Fmoc-D-proline, as an important chiral compound, has a wide range of applications in fields such as biochemistry, medicinal chemistry, and organic synthesis.
(1) Chiral protecting group: In peptide synthesis, as the Fmoc protecting form of D-proline, it is widely used as a chiral protecting group. The Fmoc group is easily removed under mild alkaline conditions, allowing D-proline to be added to the polypeptide chain according to the predetermined sequence. This selective protection strategy is crucial for synthesizing peptides with specific stereoconfigurations.
(2) Constructing chiral centers: D-proline itself has chiral centers, so introducing this substance in peptide synthesis can directly construct chiral centers, which is of great significance for the synthesis of chiral peptide drugs with biological activity.
(3) Chiral Separation: As a chiral compound, it can also be used in chiral separation experiments to achieve effective separation of racemic mixtures by forming diastereomer salts or complexes.
In the presence of alkali, it is obtained by reacting 9-fluorenylmethoxycarbonyl chloride with D-proline. This method is simple to operate, mild in reaction conditions, high in yield, and widely applicable for the preparation of product. The synthesis reaction equation of FMOC-D-proline is shown in the following figure:
Method 1:
Dissolve D-proline in 115ml of 10% sodium carbonate aqueous solution.
This step is a physical dissolution process, without a chemical equation.
Cool the dissolved solution to -4-0 ℃.
This step is a physical cooling process, and there is also no chemical equation.
Dissolve 9-fluorenylmethoxycarbonyl chloride in 35.0ml of acetone and add dropwise to the cooled system.
This step is also a physical dissolution and dropwise addition process, without chemical equations. But the subsequent reaction is a crucial step.
After the dropwise addition is complete, stir in an ice bath for 30 minutes, and then stir at room temperature for 2.0 hours.
During this process, 9-fluorenylmethoxycarbonyl chloride undergoes acylation reaction with the amino group of D-proline to produce. But the specific chemical equation has been given in the previous description and will not be repeated here.
Monitor the progress of the reaction using thin-layer chromatography.
This step is an analytical process, without chemical equations.
After the reaction is complete, pour the mixture into 400ml of water.
This step is a physical dilution process, without chemical equations.
Extract twice with ether.
This step is a physical extraction process used to extract the product, without a chemical equation.
Cool and adjust the pH to around 2 with concentrated hydrochloric acid, resulting in the precipitation of a large amount of white solid.
This step involves adjusting the pH and precipitating the product. Although the specific chemical equation is difficult to write, it can be understood that Fmoc-D-proline precipitates from the solution under acidic conditions.
Extract three times with 50ml of ethyl acetate.
This step is a physical extraction process used to further extract the product, without a chemical equation.
Dry with anhydrous magnesium sulfate.
This step is a physical drying process used to remove moisture, without a chemical equation. But magnesium sulfate may absorb moisture to form hydrated magnesium sulfate, as previously mentioned.
Remove the solvent by vacuum distillation.
This step is a physical distillation process used to remove solvents, without chemical equations.
Use petroleum ether to precipitate product.
This step is the physical precipitation process, which involves changing the solvent conditions to precipitate the product without a chemical equation.
In summary, the chemical synthesis steps include dissolution, cooling, dropwise addition, stirring reaction, monitoring progress, post-treatment (dilution, extraction, pH adjustment, precipitation), extraction and purification (extraction, drying, distillation, precipitation). The key chemical reaction in this process is the acylation reaction between 9-fluorenylmethoxycarbonyl chloride and D-proline. The other steps mainly involve physical operations, which are crucial for the purification and collection of the product. Through these steps,it can be prepared.
What is the price range of this compound?
► Price Range
According to market quotations, the price of this compound typically ranges from a few hundred to several thousand yuan, depending on various factors mentioned above. For example, some suppliers may offer lower prices, but may have lower purity or specifications; And some high-purity or special specification substances may have higher prices.
► Price influencing factors
Purity
Purity is one of the important factors affecting the price of the compound. High purity products are usually more expensive because their preparation process is more complex and requires higher technical requirements.
Specifications
The specifications will also affect the price of the compound. Products of different specifications (such as different packaging sizes and purity levels) may have different prices.
Supplier
The price of this compound provided by different suppliers may vary. This may be due to differences in production costs, sales strategies, brand influence, and other factors.
Market supply and demand situation
The supply and demand situation of this compound in the market will also affect its price. If market demand exceeds supply, prices may rise; On the contrary, if supply exceeds demand, prices may decrease.
► Get price advice
To obtain an accurate price for this compound, it is recommended to take the following measures:
- Contact suppliers: directly contact suppliers or manufacturers to obtain the latest quotes and price information.
- Compare prices: Compare multiple suppliers to obtain the most favorable price and best service.
- Consider bulk purchase: If you need to purchase a large quantity of this compound, you can consider negotiating the bulk purchase price with the supplier to obtain a more favorable price.
- Pay attention to market dynamics: Monitor the supply and demand situation and price trends of the compound in the market in order to make purchases at the appropriate time.
Is there any other amino acid with self-assembly properties comparable to this compound?
Other amino acids or their derivatives that can rival Fmoc-D-proline in terms of self-assembly properties include:
● Fmoc Phe Phe OH (Fmoc Phe Phe Phe OH): This dipeptide can form a stable hydrogel in the water environment, and shows a non centrosymmetric β - folded structure, has mechanical properties equivalent to biological gel, and shows piezoelectric behavior, making it a potential scaffold material in tissue engineering.
● Fmoc-F5-Phe (Fmoc-5-fluorophenylalanine): it can be co assembled with Fmoc-Phe-Phe-OH to form a super rigid hydrogel, which has controllable mechanical properties and is suitable for tissue engineering.
● Fmoc halogenated phenylalanine hydrogels: For example, Fmoc-4F-Phe-OH (Fmoc-4-fluorophenylalanine) is considered to be the most suitable because of the stacking effect of its fluoroene groups, although these hydrogels are not used as bioactive scaffolds for NIH 3T3 cell culture.
● α. β - didehydro - α - amino acids (α, β - didehydro - α - amino acids): These unnatural amino acids show the ability to form hydrogels due to their planar conformation and fixed torsion angle, and are used in drug delivery.
● H-Phe Phe OH (phenylalanine phenylalanine hydroxy): this dipeptide promotes self-assembly and gel through π - π stacking and hydrophobic interaction to build gel materials.
● Fmoc Leu Leu OMe: This tripeptide forms self-assembled nanoparticles, serving as a carrier for hydrophobic porphyrin derivatives, enhancing the solubility and bioavailability of hydrophobic drugs.
● Boc Pro Phe Gly OMe (Boc proline phenylalanine glycine methoxy): This protected tripeptide can encapsulate hydrophobic drugs such as fluorescein, aspirin, and curcumin, demonstrating potential as a drug carrier.
Challenges in Using Fmoc-D-Proline
► Racemization Risk
Although the Fmoc protecting group helps to reduce the risk of racemization compared to some other protecting groups, there is still a potential for racemization to occur during the coupling step, especially when using certain coupling reagents or under harsh reaction conditions. Racemization can lead to the formation of a mixture of D- and L-enantiomers of the peptide, which can affect its biological activity and purity. To minimize racemization, chemists need to carefully select coupling reagents, control reaction conditions, and use appropriate additives.
► Difficult Coupling for Some Sequences
In some peptide sequences, the coupling of Fmoc-D-proline or other amino acids can be challenging due to steric hindrance or the presence of secondary structures in the growing peptide chain. This can result in low coupling efficiencies and incomplete peptide synthesis. To overcome this problem, various strategies can be employed, such as using pseudoproline dipeptides, which can disrupt the secondary structure and improve coupling efficiency, or optimizing the coupling conditions, such as increasing the reaction time or temperature.
Fmoc-D-proline is a fundamental building block in peptide synthesis, offering numerous advantages such as mild deprotection conditions, UV monitoring capabilities, and compatibility with a wide range of reagents. Its incorporation into peptides can enhance their stability and biological activity, making it a valuable tool in the development of therapeutic and bioactive peptides. However, challenges such as racemization risk and difficult coupling for some sequences need to be addressed. With ongoing research and development, new coupling methods, applications in peptide libraries, and sustainable synthesis approaches are expected to further expand the utility of Fmoc-D-proline in the field of peptide chemistry.
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