+8613708084407
🧬 Chemical Identity
-
IUPAC Name: (4S)-3-[(2S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-phenylpropanoyl]-2,2-dimethyl-1,3-oxazolidine-4-carboxylic acid
-
Molecular Formula: C₃₀H₃₀N₂O₆
-
Molecular Weight: 514.57 g/mol
-
SMILES: CC1(N(C(CO1)C(=O)O)C(=O)C(CC2=CC=CC=C2)NC(=O)OCC3C4=CC=CC=C4C5=CC=CC=C35)C
-
InChI Key: PQJUKTSKOYOXMZ-UIOOFZCWSA-N
🧪 Structural Features
This compound contains a pseudoproline motif where the serine residue is converted into a 2,2-dimethyl-1,3-oxazolidine ring. This structural modification introduces conformational constraints that prevent hydrogen bonding along the peptide backbone, thus reducing aggregation during synthesis. The Fmoc group is a standard -labile protecting group used in solid-phase peptide synthesis (SPPS), stable in acidic environments and easily removable with piperidine.
👉 Wikipedia: Fmoc Protecting Group
⚙️ Mechanism in Peptide Synthesis
Fmoc-Phe-Ser(ψMe,Mepro)-OH temporarily disrupts peptide chain conformations, reducing aggregation by hindering secondary structure formation. During acidolytic cleavage, the pseudoproline ring reverts to a native serine residue, preserving the natural sequence of the final peptide.
💧 Solubility and Storage
-
Solubility: Soluble in DMSO up to 250 mg/mL. Ultrasonication may be used to enhance dissolution.
-
Storage:
-
As powder: Store at -20°C for long-term stability.
-
In solution: Aliquot and store at -80°C for up to 6 months or at -20°C for up to 1 month. Avoid repeated freeze-thaw cycles.
-
🧩 Application in Peptide Synthesis
Ideal for use in peptide sequences containing the Phe-Ser motif, which are prone to aggregation. Enhances synthesis of difficult peptides, especially long or hydrophobic chains, improving both purity and overall yield.
