Fmoc-L-phenylalanine (Fmoc-Phe-OH) is a cornerstone in the synthesis of peptides, a class of molecules with immense significance in biology and medicine. Understanding its structure, how it's synthesized, and its broad applications provides valuable insight into its importance in scientific research and development. The molecule combines the amino acid L-phenylalanine with the Fmoc protecting group, a combination that makes it exceptionally useful for controlled peptide chain elongation.

The chemical structure of Fmoc-Phe-OH features the characteristic Fmoc group attached to the alpha-amino nitrogen of phenylalanine. This N-terminal protection is labile under mild basic conditions, allowing for selective deprotection without damaging the growing peptide chain or its sensitive side chains. Phenylalanine itself contributes an aromatic benzyl side chain, imparting hydrophobicity and specific structural properties to the peptides it forms. The precise molecular formula is C24H21NO4, and its molecular weight is approximately 387.4 g/mol. The CAS number, 35661-40-6, is a unique identifier for this compound.

The synthesis of Fmoc-Phe-OH typically involves the reaction of L-phenylalanine with Fmoc-Cl (9-fluorenylmethoxycarbonyl chloride) or Fmoc-OSu (N-(9-fluorenylmethoxycarbonyloxy)succinimide) under basic conditions. This process selectively introduces the Fmoc group onto the amine nitrogen. High purity is crucial for its application in SPPS, and reputable manufacturers like NINGBO INNO PHARMCHEM CO.,LTD. employ rigorous quality control measures to ensure product integrity. These measures often include analytical techniques like HPLC and NMR to verify purity and structural identity.

The primary application of Fmoc-Phe-OH is in solid-phase peptide synthesis (SPPS). Here, it is sequentially coupled to a resin-bound peptide chain, followed by Fmoc deprotection and addition of the next amino acid. Its excellent solubility in common SPPS solvents such as DMF and NMP further enhances its utility. Beyond standard peptide synthesis, Fmoc-Phe-OH finds use in Structure-Activity Relationship (SAR) studies, where modifications to peptide sequences are made to understand their biological activity. It is also employed in the development of peptidomimetics and novel biomaterials, such as hydrogels, due to the self-assembly properties of certain Fmoc-amino acid derivatives.

The price of Fmoc-Phe-OH can vary based on quantity and supplier, but investing in high-quality material from trusted sources ensures successful outcomes in sensitive research. NINGBO INNO PHARMCHEM CO.,LTD. is a reliable provider of this essential reagent, contributing to advancements across various scientific disciplines by making high-purity Fmoc-Phe-OH accessible.

In summary, Fmoc-Phe-OH is a chemically well-defined and synthetically accessible molecule that plays a pivotal role in peptide chemistry. Its structure facilitates controlled synthesis, its reliable synthesis ensures quality, and its diverse applications underscore its importance in advancing research in pharmaceuticals, biochemistry, and material science.