FMOC-L-4-Fluorophe, CAS No. 169243-86-1

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169243-86-1

Catalog No. EBD2200107

CAS 169243-86-1

Name FMOC-L-4-Fluorophe

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Basic Information

Synonyms: L-Phenylalanine,N-[(9H-fluoren-9-ylmethoxy)carbonyl]-4-fluoro- l-4-fluorophenylalanine,fmocprotected (l)-4-fluoro-phenyl-n-fmoc-alanine fmoc-(s)-2-amino-3-(4'-fluorophenyl)propanoicacid fmoc-phe(pf)-oh fmoc-pf-l-phe-oh fmoc-p-fluoro-phenylalanine Fmoc-4-Fluoro-L-Phe-OH Fmoc-4-Fluoro-L-phenylalanine (S)-N-FMOC-4-Fluorophenylalanine Fmoc-L-4-Fluorophenylalanine N-(9-Fluorenylmethoxycarbonyl)-4-fluorophenyl-L-alanine

Molecular Formula: C24H20FNO4

Molecular Weight: 405.42

MDL Number: MFCD00191197

Categories: Medicinal Chemistry > Biochemicals and Life Science Reagents > Peptides and Peptidomimetics Synthetic Chemistry > Organic Building Blocks > Amines

Product Description:

Fmoc-L-4-fluorophenylalanine is a fluorinated, non-natural amino acid derivative widely used in solid-phase peptide synthesis (SPPS). It features a fluorenylmethyloxycarbonyl (Fmoc) protecting group on the α-amino group, which is stable under basic conditions but readily cleaved by piperidine, making it a standard building block in Fmoc-based SPPS strategies. The incorporation of a fluorine atom at the para-position of the phenylalanine side chain introduces unique electronic and steric properties, allowing for the modulation of peptide conformation, stability, and biological activity. Its primary application is in the research and development of therapeutic peptides and peptidomimetics. The fluorine atom can enhance metabolic stability, influence lipophilicity, and serve as a bioisostere for hydrogen or hydroxyl groups, making it valuable for structure-activity relationship (SAR) studies and drug discovery. This derivative is essential for synthesizing peptides with tailored properties for pharmaceutical and biochemical research. Beyond its role as a specialized peptide building block, it also serves as a valuable chiral amine synthon in organic synthesis. The presence of both the protected amine and carboxylic acid functionalities makes it a versatile intermediate for constructing more complex molecules. Standard handling precautions for amino acids and Fmoc-protected compounds apply, including storage in a cool, dry place and protection from light.

Physical Properties

Melting Point: 185.4 °C

Boiling Point: 623.9 °C at 760 mmHg

Flash Point: 331.1 °C

Density: 1.317 g/cm3

Storage: 2-8°C

Analytical Data

Appearance: white fluffy powder