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Fmoc-PHE-OH
CAS: 35661-40-6
SKU: S2329
Fmoc-PHE-OH | SKU: S2329
Synonyms: Fmoc-L-phenylalanine; N-Fmoc-L-phenylalanine; N-(9-Fluorenylmethoxycarbonyl)-L-phenylalanine; Nα-Fmoc-L-phenylalanine
Fmoc-PHE-OH
Fmoc-Phe-OH, or N-(9-fluorenylmethoxycarbonyl)-L-phenylalanine, is the Fmoc-protected form of the amino acid L-phenylalanine and one of the standard building blocks of Fmoc solid-phase peptide synthesis (SPPS). It is a white crystalline powder with a reference assay of 98%, a melting range of 180–187 °C and a specific rotation of −37° (c = 1 in DMF). The Fmoc group protects the α-amino group during chain assembly and is removed under mild basic conditions, typically with piperidine in DMF, leaving acid-labile side-chain protection untouched. That orthogonality is why Fmoc amino acids dominate research peptide synthesis, and increasingly the manufacture of peptide active pharmaceutical ingredients. Phenylalanine contributes a hydrophobic aromatic side chain that drives binding, folding and self-assembly in many bioactive peptides. Sarchem Labs provides Fmoc-Phe-OH for peptide laboratories, contract synthesis groups and peptide-drug developers. Every lot is documented with a Certificate of Analysis and Safety Data Sheet, and bulk quantities can be quoted on request.
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Specifications

Melting Point180–187°C (lit.)
ColorWhite
Formula Weight387.44
Physical FormCrystal-powder at 20°C
Chemical Name or MaterialN-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-phenylalanine
Molecular Weight387.43 g/mol
SMILES StringOC(=O)[C@H](Cc1ccccc1)NC(=O)OCC2c3ccccc3-c4ccccc24
Assay98%
CAS Number35661-40-6
Storage Temperature2–8°C
EC Number252-661-1
NACRESNA.26
PubChem Substance ID24860536
UNSPSC Code12352209
MDL NumberMFCD00037128
InChI1S/C24H21NO4/c26-23(27)22(14-16-8-2-1-3-9-16)25-24(28)29-15-21-19-12-6-4-10-17(19)18-11-5-7-13-20(18)21/h1-13,21-22H,14-15H2,(H,25,28)(H,26,27)/t22-/m0/s1
InChI KeySJVFAHZPLIXNDH-QFIPXVFZSA-N
PubChem CID978331
eCl@ss32160406
Reaction SuitabilityReaction type: C–H activation; Fmoc solid-phase peptide synthesis; peptide synthesis; reagent type: ligand
Beilstein/REAXYS Number3597808
Quality Level200
Optical Activity[α]20/D −37°, c = 1 in DMF
Functional GroupsFmoc, amine, carboxylic acid
Empirical Formula (Hill Notation)C24H21NO4
ApplicationPeptide synthesis
ApplicationsFmoc solid-phase peptide synthesis: installs L-phenylalanine residues in research peptides, peptide libraries, epitope mimics and therapeutic peptide candidates.

Applications

Fmoc solid-phase peptide synthesis: installs L-phenylalanine residues in research peptides, peptide libraries, epitope mimics and therapeutic peptide candidates.
Peptide API development and manufacturing: a core raw material for peptide-based drug candidates, where Phe residues often anchor receptor binding through aromatic and hydrophobic interactions.
Self-assembling biomaterials: Fmoc-amino acids, Fmoc-Phe among them, can self-assemble through π–π stacking of the fluorenyl groups into nanofibrous hydrogels studied for drug delivery, cell culture and tissue engineering.
Ligand in C–H activation: protected amino acids of this type are used as chiral or mono-protected ligands in palladium-catalysed C–H functionalisation, as noted on the reference listing.
Medicinal chemistry: building block for peptidomimetics, enzyme-substrate probes and fluorescent or radiolabelled peptide tools.
Analytical and educational use: a standard demonstration amino acid for peptide-coupling and deprotection experiments in teaching laboratories.

Product Description

What is Fmoc-Phe-OH?

Fmoc-Phe-OH is L-phenylalanine whose α-amino group has been converted to a 9-fluorenylmethyl carbamate. It has the formula C24H21NO4 and a molecular weight of 387.43 g/mol. The free carboxylic acid is the coupling site: activated with a carbodiimide, uronium or phosphonium reagent, it forms an amide bond with the amine of the growing peptide chain.

The fluorenyl ring system is both UV-active, which allows deprotection to be monitored at about 300 nm, and base-labile, because piperidine abstracts the acidic proton at C-9 and triggers elimination of dibenzofulvene. Sigma-Aldrich lists the reference grade at 98% with a specific rotation of −37° in DMF and a recommended storage temperature of 2–8 °C.

Uses of Fmoc-Phe-OH

In peptide laboratories, it is used wherever a sequence contains phenylalanine, which includes most opioid peptides, many hormone analogues, antimicrobial peptides and numerous protease-substrate sequences. Chemists couple it with reagents such as DIC/Oxyma, HBTU or HATU in DMF or NMP, remove the Fmoc group with piperidine, and repeat the cycle until the peptide is complete.

In the pharmaceutical supply chain, it is a high-volume raw material for peptide drugs, where lot-to-lot purity and low levels of dipeptide or free amino acid impurities matter. Materials scientists use the same compound to form Fmoc-based supramolecular gels, and organometallic chemists use protected amino acids of this family as ligands.

Buying and Handling Considerations

For SPPS, three quality attributes matter most: HPLC purity, enantiomeric purity and free-amino-acid content. Free amino acid can cause double insertions, and D-isomer contamination produces diastereomeric peptide impurities that are hard to remove. Request the lot-specific values from the Certificate of Analysis. Store at 2–8 °C in a tightly closed container, protect from moisture, and allow the bottle to reach room temperature before opening so that water does not condense on the powder.

Safety Information

Based on Sigma-Aldrich’s verified listing (338338).

  • GHS Classification: no pictogram, signal word or hazard statement assigned in the reference listing
  • Storage Class: 11 – Combustible solids | WGK: 3 | Flash Point: not applicable
  • PPE: Eyeshields, gloves, type N95 (US) dust mask

Handle as a fine organic powder: weigh in a ventilated enclosure, avoid dust formation and inhalation, and keep away from sources of ignition. Piperidine and DMF used with this reagent have their own hazards and require separate review.

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FAQs: Fmoc-PHE-OH

It is used to add L-phenylalanine residues during Fmoc solid-phase peptide synthesis. It is a standard raw material for research peptides, peptide libraries and peptide drug candidates, and it is also studied for self-assembling hydrogels and as a ligand in palladium-catalysed C–H activation.

Fmoc stands for 9-fluorenylmethoxycarbonyl, an amine-protecting group that is stable to acids but removed by mild bases such as 20% piperidine in DMF. That makes it compatible with acid-labile side-chain protecting groups.

The formula is C24H21NO4 and the molecular weight is 387.43 g/mol. The reference grade has a melting range of 180–187 °C and a specific rotation of −37° (c = 1 in DMF).

Yes. Fmoc-Phe-OH, Fmoc-L-phenylalanine and N-Fmoc-L-phenylalanine are the same compound, CAS 35661-40-6. The D-enantiomer, Fmoc-D-Phe-OH, has a different CAS number and should not be substituted.

Store it at 2–8 °C in a tightly closed container, away from moisture, light and strong bases. Let the container warm to room temperature before opening to avoid condensation.

The reference listing assigns no GHS hazard statement. It is a combustible solid (storage class 11), so use an N95-type dust mask, eyeshields and gloves and prevent dust accumulation.

Yes. Each lot of SKU S2329 ships with a Certificate of Analysis and Safety Data Sheet, and Sarchem Labs quotes laboratory to bulk quantities.