Fmoc-Val-Ala-PAB-PFP - CAS 2348406-01-7

Fmoc-Val-Ala-PAB-PFP - CAS 2348406-01-7 Catalog number: BADC-01485

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Fmoc-Val-Ala-PAB-PFP is a type of small molecule linker that is often used in the field of bioconjugation and drug delivery.

Category
ADCs Linker
Product Name
Fmoc-Val-Ala-PAB-PFP
CAS
2348406-01-7
Catalog Number
BADC-01485
Molecular Formula
C37H32F5N3O7
Molecular Weight
725.66
Fmoc-Val-Ala-PAB-PFP

Ordering Information

Catalog Number Size Price Quantity
BADC-01485 -- $-- Inquiry
Description
Fmoc-Val-Ala-PAB-PFP is a type of small molecule linker that is often used in the field of bioconjugation and drug delivery.
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.

The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

The dilution calculator equation

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

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