Fmoc-Val-D-Cit-PAB - CAS 1350456-67-5

Fmoc-Val-D-Cit-PAB - CAS 1350456-67-5 Catalog number: BADC-00930

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Category
ADCs Linker
Product Name
Fmoc-Val-D-Cit-PAB
CAS
1350456-67-5
Catalog Number
BADC-00930
Molecular Formula
C33H39N5O6
Molecular Weight
601.69
Purity
≥95%

Ordering Information

Catalog Number Size Price Quantity
BADC-00930 -- $-- Inquiry

Related Molecules

Synonyms
9H-fluoren-9-ylmethyl N-[(2S)-1-[[(2R)-5-(carbamoylamino)-1-[4-(hydroxymethyl)anilino]-1-oxopentan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]carbamate
Canonical SMILES
CC(C)C(C(=O)NC(CCCNC(=O)N)C(=O)NC1=CC=C(C=C1)CO)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24
InChI
InChI=1S/C33H39N5O6/c1-20(2)29(38-33(43)44-19-27-25-10-5-3-8-23(25)24-9-4-6-11-26(24)27)31(41)37-28(12-7-17-35-32(34)42)30(40)36-22-15-13-21(18-39)14-16-22/h3-6,8-11,13-16,20,27-29,39H,7,12,17-19H2,1-2H3,(H,36,40)(H,37,41)(H,38,43)(H3,34,35,42)/t28-,29+/m1/s1
InChIKey
DALMAZHDNFCDRP-WDYNHAJCSA-N
Solubility
10 mm in DMSO
Shelf Life
≥ 2 years
Shipping
-20°C (International: -20°C)

Fmoc-Val-D-Cit-PAB is a specialized compound used in peptide synthesis and targeted drug delivery applications. The Fmoc (9-fluorenylmethyloxycarbonyl) group serves as a protective group for the N-terminal amino group, facilitating controlled peptide chain assembly through solid-phase peptide synthesis (SPPS). This protection ensures high specificity and efficiency during synthesis, making the compound an essential building block for complex peptide-based systems.

The Val-D-Cit (valine-D-citrulline) dipeptide sequence in Fmoc-Val-D-Cit-PAB is particularly notable for its role in enzyme-sensitive linker design. This sequence is recognized and cleaved by specific proteases, such as cathepsins, which are overexpressed in certain pathological conditions like cancer. As a result, this compound is widely used in the development of peptide-drug conjugates (PDCs) and antibody-drug conjugates (ADCs), where it enables the precise release of cytotoxic agents in the tumor microenvironment.

The PAB (para-aminobenzyl) moiety in Fmoc-Val-D-Cit-PAB acts as a self-immolative spacer, enabling the efficient release of attached drugs or bioactive molecules upon enzymatic cleavage of the Val-D-Cit sequence. This unique property ensures that the therapeutic payload is released in its active form at the target site, reducing systemic toxicity and enhancing therapeutic efficacy. This feature is critical in the design of advanced drug delivery systems for cancer and other diseases requiring localized treatment.

Fmoc-Val-D-Cit-PAB is also used in the synthesis of prodrug systems and stimuli-responsive biomaterials. The Val-D-Cit sequence can be engineered to respond to specific biological stimuli, such as protease activity or pH changes, enabling controlled drug release. These properties make the compound suitable for creating smart drug delivery platforms that improve drug stability, bioavailability, and targeting precision.

In addition to therapeutic applications, Fmoc-Val-D-Cit-PAB is employed in bioconjugation and biomaterial functionalization. Its modular structure allows it to be incorporated into nanoparticles, hydrogels, and other carrier systems for targeted delivery or diagnostic purposes. The combination of enzymatic sensitivity, self-immolative behavior, and efficient synthesis capabilities makes Fmoc-Val-D-Cit-PAB a valuable tool in both pharmaceutical research and biomedical engineering.

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

Historical Records: Fmoc-Val-D-Cit-PAB
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