Fmoc-Arg(pbf)-OH is an arginine derivative containing the amine-protecting group Fmoc, with the full Chinese name being N-Fluorenylmethoxycarbonyl-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine. The detailed information is as follows:
1. Basic Information
Chemical Formula: C₃₄H₄₀N₄O₇S
Molecular Weight: 648.77
CAS Number: 154445-77-9
2. Structural Features
It consists of three components:
N-Fluorenylmethoxycarbonyl (Fmoc): A common amino-protecting group that shields the amino group.
2,2,4,6,7-Pentamethyldihydrobenzofuran-5-sulfonyl (Pbf): A sulfonylated reagent that protects the guanidino group on arginine’s side chain.
L-Arginine: The amino acid moiety.
Structural Modification Benefits:
The Fmoc group ensures orthogonal protection of the α-amino group during peptide synthesis.
The Pbf group neutralizes the basicity of arginine’s guanidino group, enhancing solubility in organic solvents (e.g., DMF, DCM) and facilitating downstream separation/purification.
3. Applications
As a key building block for introducing arginine into solid-phase peptide synthesis (SPPS), it enables:
Efficient Peptide Assembly: Selective protection/deprotection of functional groups ensures high-specificity peptide elongation.
Complex Peptide Synthesis: Widely used in constructing arginine-rich peptides (e.g., cell-penetrating peptides, antimicrobial peptides) and pharmaceutical intermediates (e.g., GLP-1 analogs).
4. Physicochemical Properties
Appearance: White crystalline powder.
Storage Conditions:
Store in a cool, dry, and well-ventilated environment.
Recommended storage temperature: -20°C.
Avoid contact with strong oxidizing agents.
This derivative is indispensable in modern peptide chemistry, balancing reactivity and stability to support advanced peptide synthesis in both research and industrial applications.
