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Usage

Uses

Used in Pharmaceutical Industry:
(4R)-4-Fluoro-L-Proline HCL is used as a key building block in the synthesis of various pharmaceutical compounds for its enhanced biological activity and improved pharmacokinetic properties. The incorporation of a fluorine atom into the proline molecule allows for the development of drugs with increased potency, selectivity, and metabolic stability.
Used in Medicinal Chemistry Research:
(4R)-4-Fluoro-L-Proline HCL is utilized as an important tool in medicinal chemistry research for the creation of novel therapeutic compounds. Its unique structural features and enhanced biological activity make it a valuable component in the design and synthesis of new drugs with improved efficacy and safety profiles.
Used in Drug Development:
(4R)-4-Fluoro-L-Proline HCL plays a crucial role in the research and development of new drugs, particularly in the optimization of lead compounds and the discovery of innovative therapeutic agents. Its unique properties enable medicinal chemists to explore new chemical space and design drugs with superior pharmacological properties, ultimately contributing to the advancement of healthcare and the treatment of various diseases.

Upstream product

• 203866-18-6 methyl (2S,4R)-N-(tert-butyloxy)carbonyl-4-fluoropyrrolidine-2-carboxylate 

Relevant academic research and scientific papers

Automated Radiosynthesis of cis- And trans-4-[18F]Fluoro- l -proline Using [18F]Fluoride

The positron emission tomography imaging agents cis- and trans-4-[18F]fluoro-l-proline are used for the detection of numerous diseases such as pulmonary fibrosis and various carcinomas. These imaging agents are typically prepared by nucleophilic fluorination of 4-hydroxy-l-proline derivatives, with [18F]fluoride, followed by deprotection. Although effective radiofluorination reactions have been developed, the overall radiosynthesis process is suboptimal due to deprotection methods that are performed manually, require multiple steps, or involve harsh conditions. Here we describe the development of two synthetic routes that allow access to precursors, which undergo highly selective radiofluorination reactions and rapid deprotection, under mild acidic conditions. These methods were found to be compatible with automation, avoiding manual handling of radioactive intermediates.

Synthesis and antibacterial activity of 6(R)- and 6(S)-fluoropenibruguieramine As: Fluorine as a probe for testing the powerfulness of memory of chirality (MOC)

The synthesis of 6(R)- and 6(S)- fluoropenibruguieramine As has been achieved, employing the elegant strategy developed by Kim and co-workers. Single diastereomers were formed via the key intramolecular aldol reaction, and both of the products were unambiguously confirmed by X-ray diffraction crystallography. This reaction shows that the fluorine amide effect could not compete with the memory of chirality (MOC) effect, thus further demonstrating the powerfulness of MOC effect in asymmetric synthesis. The biological testing carried out in this work indicates that the principal of antibacterial activity of the natural extract is probably not penibruguieramine A.

Practical syntheses of 4-fluoroprolines

4-Fluoroprolines are among the most useful nonnatural amino acids in chemical biology. Here, practical routes are reported for the synthesis of the 2S,4R, 2S,4S, and 2R,4S diastereomers of 4-fluoroproline. Each route starts with (2S,4R)-4-hydroxyproline, which is a prevalent component of collagen and hence readily available, and uses a fluoride salt to install the fluoro group. Hence, the routes provide process-scale access to these useful nonnatural amino acids.