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N3-L-Dab(Fmoc)-OH

  CAS No.: 2250436-44-1   Cat No.: BADC-01795 4.5  

N3-L-Dab(Fmoc)-OH is an azide-functionalized amino acid intermediate tailored for ADC linker synthesis, enabling controlled conjugation via click chemistry. It contributes to enhanced drug delivery specificity in antibody-drug conjugates. Keywords: ADC linker, azide linker, amino acid linker, click chemistry.

N3-L-Dab(Fmoc)-OH

Structure of 2250436-44-1

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ADC Linker
Molecular Formula
C19H18N4O4
Molecular Weight
366.37

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IUPAC Name
(2S)-2-azido-4-(9H-fluoren-9-ylmethoxycarbonylamino)butanoic acid
Canonical SMILES
C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NCCC(C(=O)O)N=[N+]=[N-]
InChI
InChI=1S/C19H18N4O4/c20-23-22-17(18(24)25)9-10-21-19(26)27-11-16-14-7-3-1-5-12(14)13-6-2-4-8-15(13)16/h1-8,16-17H,9-11H2,(H,21,26)(H,24,25)/t17-/m0/s1
InChIKey
ZWTIWUGRZMLNNV-KRWDZBQOSA-N

N3-L-Dab(Fmoc)-OH is an important building block in peptide synthesis, particularly for introducing 2,4-diaminobutyric acid (Dab) into peptide sequences. The Fmoc (fluorenylmethyloxycarbonyl) protecting group on the amino group of Dab allows for controlled deprotection during solid-phase peptide synthesis (SPPS), making it easier to add Dab to peptides without affecting other sensitive residues. This protected form of Dab is widely used to synthesize peptides with enhanced properties for therapeutic and research applications.

A key application of N3-L-Dab(Fmoc)-OH is in the creation of peptides with structural diversity and improved bioactivity. The inclusion of Dab in peptide sequences can introduce additional flexibility and enhance interactions with target proteins, enzymes, or receptors. Peptides containing Dab residues are often used in the development of enzyme inhibitors, antimicrobial peptides, and other bioactive peptides that require specific structural characteristics for optimal function. The N3-protection ensures efficient synthesis while preserving the integrity of the peptide.

Another significant application of N3-L-Dab(Fmoc)-OH is in the synthesis of peptide-based drug delivery systems. Dab-containing peptides can be used as carriers for drug molecules, offering improved stability, solubility, and cellular uptake. By incorporating Dab into peptide-drug conjugates (PDCs), researchers can develop more effective targeted therapies. The controlled reactivity provided by the Fmoc-protection group allows for the precise attachment of drugs or targeting agents to the peptide backbone, ensuring efficient delivery to the desired site of action, such as tumor cells or specific tissues.

N3-L-Dab(Fmoc)-OH is also employed in the development of cyclic peptides. The presence of the Dab residue in cyclic peptide sequences contributes to increased flexibility and stability. This is crucial for creating peptides that can bind with high specificity to target proteins or enzymes. Dab-containing cyclic peptides are being explored for their potential in drug discovery, particularly for targeting protein-protein interactions and inhibiting enzyme activities, which is vital for treating diseases such as cancer and neurodegenerative disorders.

Lastly, N3-L-Dab(Fmoc)-OH is useful in peptide vaccine development. The inclusion of Dab in vaccine peptides can enhance the stability and immunogenicity of the vaccine. By using Dab to design peptides that mimic specific disease-causing agents, researchers can create more effective vaccines, particularly in the fields of cancer immunotherapy, infectious disease prevention, and autoimmune disease management. The Fmoc protection of the Dab residue ensures that these peptides can be synthesized efficiently with minimal risk of unwanted reactions.

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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