Name: Fmoc-Asp-NH2
Brand: BOC Sciences
Rating: 5 (1 reviews)

Synonyms

Fmoc-L-Isoasparagine; Fmoc-Isoasn-OH; Butanoic acid, 4-amino-3-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-4-oxo-, (3S)-

IUPAC Name

(3S)-4-amino-3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxobutanoic acid

Canonical SMILES

C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CC(=O)O)C(=O)N

InChI

InChI=1S/C19H18N2O5/c20-18(24)16(9-17(22)23)21-19(25)26-10-15-13-7-3-1-5-11(13)12-6-2-4-8-14(12)15/h1-8,15-16H,9-10H2,(H2,20,24)(H,21,25)(H,22,23)/t16-/m0/s1

InChIKey

VHRMWRHTRSQVJJ-INIZCTEOSA-N

Density

1.362 g/cm3

Solubility

10 mm in DMSO

Melting Point

185-190 °C

Flash Point

354.2°C

Index Of Refraction

1.626

PSA

118.72000

Vapor Pressure

1.97E-18mmHg at 25°C

Appearance

White powder

Shelf Life

-20°C 3 years powder; -80°C 2 years in solvent

Shipping

Room temperature

Storage

-20°C

Boiling Point

662.1 °C at 760 mmHg

Biological Activity

Fmoc-Asp-NH2 is a cleavable ADC linker used in the synthesis of antibody-drug conjugates (ADCs). In Vitro: ADCs are comprised of an antibody to which is attached an ADC cytotoxin through an ADC linker.

Fmoc-Asp-NH2, known as Fmoc-Aspartic Acid Amide, is a critical building block in the synthesis of antibody-drug conjugates (ADCs). ADCs represent a revolutionary class of biopharmaceuticals designed for targeted cancer therapy. They combine the high specificity of monoclonal antibodies with the potent cytotoxicity of small molecule drugs. The linker, such as Fmoc-Asp-NH2, plays a crucial role in connecting these two components securely. By ensuring stability in circulation and enabling release of the drug payload within cancer cells, Fmoc-Asp-NH2 effectively enhances the efficacy and safety profile of ADCs compared to traditional chemotherapy.

The versatile chemistry of Fmoc-Asp-NH2 contributes to its widespread application in drug discovery and development. Fmoc (9-fluorenylmethoxycarbonyl) is a protecting group that allows for sequential addition of amino acids in peptide synthesis, which is integral to forming peptide linkers in ADCs. Aspartic acid provides a site for further functionalization and attachment to either the antibody or drug moiety. This modularity facilitates the design of ADCs with tailored properties, such as optimized pharmacokinetics and controlled drug release profiles. Researchers can thus fine-tune ADCs to maximize tumor eradication while minimizing off-target effects.

Fmoc-Asp-NH2’s cleavable nature is particularly beneficial in ADC technology. Cleavable linkers are designed to remain stable in the bloodstream but degrade in response to specific stimuli within the tumor microenvironment. This feature is crucial as it allows the release of the cytotoxic drug precisely at the site of the tumor, minimizing damage to healthy tissues. Enzymatic cleavage is a common strategy, where linkers like Fmoc-Asp-NH2 are sensitive to specific enzymes overexpressed in cancer cells. This ability to engineer selective drug release represents a significant advancement in personalized medicine and targeted therapy.

In the rapidly evolving landscape of oncology, Fmoc-Asp-NH2 is pivotal for the development of next-generation ADCs with enhanced therapeutic windows. Pharmaceutical researchers leverage its properties to overcome challenges such as drug resistance and heterogeneity of cancer cells. Combining advanced molecular biology techniques with the strategic use of linkers like Fmoc-Asp-NH2 allows for the production of more sophisticated ADCs, potentially leading to better patient outcomes. The strategic manipulation of ADC components can also lead to dual-targeting strategies or the incorporation of immune-stimulatory agents, broadening the scope of ADC applications.