Name: Fmoc-Val-Ala-PAB-PFP
Brand: BOC Sciences
Rating: 5 (1 reviews)

IUPAC Name

[4-[[(2S)-2-[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-methylbutanoyl]amino]propanoyl]amino]phenyl]methyl (2,3,4,5,6-pentafluorophenyl) carbonate

Canonical SMILES

CC(C)C(C(=O)NC(C)C(=O)NC1=CC=C(C=C1)COC(=O)OC2=C(C(=C(C(=C2F)F)F)F)F)NC(=O)OCC3C4=CC=CC=C4C5=CC=CC=C35

InChI

InChI=1S/C37H32F5N3O7/c1-18(2)32(45-36(48)50-17-26-24-10-6-4-8-22(24)23-9-5-7-11-25(23)26)35(47)43-19(3)34(46)44-21-14-12-20(13-15-21)16-51-37(49)52-33-30(41)28(39)27(38)29(40)31(33)42/h4-15,18-19,26,32H,16-17H2,1-3H3,(H,43,47)(H,44,46)(H,45,48)/t19-,32-/m0/s1

InChIKey

GTTLUTNKEYUIOG-GTJUCTONSA-N

Appearance

White Solid

Fmoc-Val-Ala-PAB-PFP is a versatile compound extensively used in peptide synthesis, drug delivery systems, and bioconjugation applications. The Fmoc (9-fluorenylmethyloxycarbonyl) group protects the amino terminus, enabling stepwise solid-phase peptide synthesis (SPPS) with high precision and efficiency. This protection allows the compound to integrate seamlessly into complex peptide chains, ensuring controlled synthesis and minimal side reactions.

The Val-Ala (valine-alanine) dipeptide sequence in Fmoc-Val-Ala-PAB-PFP plays a pivotal role in creating enzyme-sensitive linkers. This sequence can be engineered as a cleavage site for specific proteases, enabling precise control over the release of attached therapeutic agents. In drug delivery applications, this property is critical for designing prodrugs and targeted delivery systems, such as peptide-drug conjugates (PDCs) and antibody-drug conjugates (ADCs). The protease-sensitive nature of the linker ensures selective activation of drugs in diseased tissues, such as tumors, minimizing off-target effects and systemic toxicity.

The PAB (para-aminobenzyl) moiety functions as a self-immolative linker in Fmoc-Val-Ala-PAB-PFP. Upon enzymatic cleavage of the Val-Ala sequence, the PAB group undergoes rapid decomposition, facilitating the release of attached payloads. This mechanism is widely exploited in the development of stimuli-responsive drug delivery systems, where the payload release is triggered by specific biological or environmental cues. This property enhances the precision and efficiency of drug delivery, particularly in advanced therapies.

The PFP (pentafluorophenyl) ester group is a highly reactive moiety that enables efficient conjugation with nucleophilic groups, such as amines or thiols. This reactivity makes Fmoc-Val-Ala-PAB-PFP a valuable tool for bioconjugation and surface modification. It is commonly used to attach peptides, proteins, or small molecules to carriers like nanoparticles, polymers, or hydrogels, facilitating their application in drug delivery, diagnostics, and biomaterial engineering.

Fmoc-Val-Ala-PAB-PFP is also instrumental in the synthesis of advanced biomaterials and functionalized surfaces. The combination of its Fmoc-protected dipeptide, self-immolative linker, and reactive ester functionality allows for the creation of smart materials with tunable properties. These materials are applied in tissue engineering, biosensing, and targeted therapeutics, where precise control over molecular interactions and release profiles is essential.