N3-Gly-Aeg(Fmoc)-OH - CAS 2606227-07-8

N3-Gly-Aeg(Fmoc)-OH - CAS 2606227-07-8 Catalog number: BADC-01759

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N3-Gly-Aeg(Fmoc)-OH is a click chemistry reagent containing an azide group.

Category
ADCs Linker
Product Name
N3-Gly-Aeg(Fmoc)-OH
CAS
2606227-07-8
Catalog Number
BADC-01759
Molecular Formula
C21H21N5O5
Molecular Weight
423.42

Ordering Information

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BADC-01759 -- $-- Inquiry
Description
N3-Gly-Aeg(Fmoc)-OH is a click chemistry reagent containing an azide group.
IUPAC Name
2-[(2-azidoacetyl)-[2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]amino]acetic acid
Canonical SMILES
C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NCCN(CC(=O)O)C(=O)CN=[N+]=[N-]
InChI
InChI=1S/C21H21N5O5/c22-25-24-11-19(27)26(12-20(28)29)10-9-23-21(30)31-13-18-16-7-3-1-5-14(16)15-6-2-4-8-17(15)18/h1-8,18H,9-13H2,(H,23,30)(H,28,29)
InChIKey
OYUSDQQCLGZRFC-UHFFFAOYSA-N

N3-Gly-Aeg(Fmoc)-OH is an important compound in peptide synthesis, where it serves as an intermediate for the incorporation of glycine and other amino acids into peptides with enhanced properties. The Fmoc (9-fluorenylmethyloxycarbonyl) protecting group is widely used in solid-phase peptide synthesis (SPPS) to protect the amine group during the elongation process, allowing for precise and efficient peptide formation. N3-Gly-Aeg(Fmoc)-OH is particularly useful in the synthesis of peptides that require specific modifications or modifications that enhance stability and biological activity.

One of the key applications of N3-Gly-Aeg(Fmoc)-OH is in the synthesis of glycine-containing peptides, particularly in the context of peptide-based therapeutics. Glycine, being one of the simplest amino acids, plays an important role in maintaining the stability and flexibility of peptide structures. The incorporation of N3-Gly-Aeg(Fmoc)-OH into peptides can improve their solubility, stability, and resistance to enzymatic degradation. This makes it valuable for developing bioactive peptides with enhanced pharmacokinetic properties, such as peptides used in cancer treatment, antimicrobial agents, or hormone replacements.

Another significant application of N3-Gly-Aeg(Fmoc)-OH is in the preparation of peptide-drug conjugates (PDCs). By linking peptides with bioactive molecules, such as cytotoxic drugs or targeting agents, PDCs offer a powerful way to deliver drugs to specific sites in the body, improving their efficacy and reducing off-target effects. The Fmoc protection allows for controlled peptide elongation while ensuring the correct incorporation of N3-Gly-Aeg residues. This has applications in targeted therapies for conditions such as cancer, autoimmune diseases, and infections, where selective targeting is critical.

In addition, N3-Gly-Aeg(Fmoc)-OH is useful in the creation of cyclic peptides and peptide mimetics. The presence of glycine in the sequence can influence the peptide’s flexibility, allowing for the formation of cyclic structures that are often more stable and resistant to proteolysis. These cyclic peptides are increasingly used in drug discovery for their ability to bind specific receptors or inhibit protein-protein interactions. The Fmoc group’s protection ensures that synthesis remains controlled, which is crucial for maintaining the desired structure and function of the cyclic peptides.

Furthermore, N3-Gly-Aeg(Fmoc)-OH plays a role in the development of functionalized materials for drug delivery and biomedical applications. The glycine residue provides a flexible backbone, while the Aeg (aminoethylglycine) and Fmoc groups allow for easy incorporation into various platforms such as nanoparticles, liposomes, or dendrimers. These functionalized materials can be used for controlled drug release, gene therapy, or targeted delivery, where the precise control over the chemical structure is critical for the therapeutic effectiveness. N3-Gly-Aeg(Fmoc)-OH is, therefore, a valuable tool in the design of advanced drug delivery systems.

Lastly, N3-Gly-Aeg(Fmoc)-OH is increasingly applied in peptide-based vaccine development. By incorporating glycine into the peptide sequence, researchers can design antigens or adjuvants that are more stable and capable of inducing a stronger immune response. Peptide vaccines often rely on precise structural design, and the versatility of N3-Gly-Aeg(Fmoc)-OH makes it an ideal choice for designing peptides that can be used to generate immunity against a variety of pathogens, including viruses, bacteria, and cancer cells.

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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