(2S,4R)-4-FLUORO-PYRROLIDINE-2-CARBOXYLIC ACID

Based information:
Product Name: (2S,4R)-4-FLUORO-PYRROLIDINE-2-CARBOXYLIC ACID
Synonyms: H-(2S,4R)-PRO(4-F)-OH;H-TRANS-4-FLUORO-PRO-OH;H-PRO(4-F)-OH;L-PROLINE, 4-FLUORO-, (4R)-;(4R)-FLUORO-L-PROLINE;(2S, 4R)-4-FLUOROPROLINE
CAS: 2507-61-1
MF: C5H8FNO2
MW: 133.12
Melting point 264°C(lit.)
Boiling point 265.1±40.0 °C(Predicted)
density 1.30±0.1 g/cm3(Predicted)
Specific Optical Rotation: ’-92° (C=1.00g/100ml, H₂O)
storage temp. Store at RT.
pka 1.88±0.40(Predicted)
Appearance White to Light yellow powder to crystal

Specification:
Purity: 98%
Supply:  Kilograms, (Large quantity need to custom synthesis)

Transport Information:
NON hazardous goods for shipment
HS Code 2933990099

Package: 
Package: Aluminum foil bag
storage temp. Store sealed at room temperature

Contact person: Crystal@coreychem.com

Applications of CAS 2507-61-1 (trans-4-Fluoro-L-proline)
1. Core Mainstream Application: Pharmaceutical R&D and Manufacturing
1.1 Key Chiral Building Block for Peptide Drug R&D and Modification
As a non-natural amino acid, it replaces natural proline into the peptide chain, which can precisely regulate the spatial conformation of the peptide, significantly improve the hydrolytic stability of the peptide against proteases in vivo, prolong the half-life of the drug, optimize lipophilicity and cell membrane penetration, and enhance bioavailability.It is widely used in the synthesis and structural optimization of therapeutic peptides such as antiviral peptides, anti-tumor peptides, GLP-1 receptor agonist hypoglycemic peptides and anti-inflammatory peptides, and is a key raw material for innovative peptide drug R&D.
1.2 Key Intermediate for Small Molecule Targeted Drugs
Its fluorinated pyrrolidine chiral core is the key structural unit of many small molecule drugs, which is used for the synthesis of high-selective target inhibitors with core application directions as follows:
Synthesis of αvβ1 integrin inhibitors (IC50 up to 0.02 nM) for R&D of anti-fibrotic and anti-tumor metastasis drugs;
Synthesis of GluK1 kainic acid receptor antagonists for research on treatment of central nervous system diseases and neurodegenerative diseases;
Synthesis of dipeptidyl peptidase (DPP-4) inhibitors and prolyl hydroxylase inhibitors for R&D of hypoglycemic, anti-fibrotic and anti-osteoporosis drugs;
Construction of monoclonal antibodies targeting the seed conformation of tau protein, providing core raw materials for R&D of therapeutic drugs for tauopathies such as Alzheimer’s disease.
1.3 API and Generic Drug Manufacturing
As a key starting material for marketed and clinical proline-derived drugs, it is used for large-scale synthesis and process optimization of active pharmaceutical ingredients (APIs), and is a core special chiral intermediate for pharmaceutical CDMO and API manufacturers.

2. Organic Synthesis and Asymmetric Catalysis
2.1 Core Skeleton of Chiral Organocatalysts
Natural proline is a classic chiral skeleton for asymmetric organocatalysis. The trans-fluorine substitution at the 4-position can precisely regulate the stereoselectivity, catalytic activity, solubility and stability of the catalyst. It is widely used in classic asymmetric synthesis reactions such as asymmetric Aldol reaction, Mannich reaction and Michael addition. Compared with natural proline, it exhibits better catalytic efficiency and enantioselectivity in both aqueous and aprotic solvents.
2.2 Chiral Building Block for Total Synthesis of Complex Molecules
As a chiral source, it is used to construct complex natural products, alkaloids and functional organic molecules containing fluorinated pyrrolidine rings. It can accurately introduce chiral centers during synthesis, simplify the synthetic route, and improve the optical purity of the target product, making it an important chiral raw material for the total synthesis of natural products.
2.3 Preparation of Chiral Analytical Reagents
It can be derivatized to prepare ¹⁹F NMR chiral probes for the detection of enantiomeric purity of chiral amino acids and chiral amines, and is an important raw material in the field of chiral drug quality control and chiral analysis.

3. Biochemistry and Basic Scientific Research
Research Tool for Enzymology and Structural Biology: As a proline structural analog, it can competitively bind to the active sites of proline-specific proteases, collagenases and peptidyl-prolyl isomerases, for research on enzyme mechanism and inhibitor screening. It can also regulate the secondary structure and conformational stability of proteins by site-specific substitution of proline residues in proteins, for research on protein folding mechanism and function of structural proteins such as collagen.
Biomarker and Imaging: Relying on the nuclear magnetic resonance properties of ¹⁹F, it is used as a bioorthogonal labeling reagent for ¹⁹F NMR labeling and background-free imaging of peptides and proteins in vitro and in vivo, and is an important tool for in vivo biomolecular tracing research.