Name: N3-D-Dab(Boc)-OH
Brand: BOC Sciences
Rating: 5 (1 reviews)

IUPAC Name

(2R)-2-azido-4-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid

Canonical SMILES

CC(C)(C)OC(=O)NCCC(C(=O)O)N=[N+]=[N-]

InChI

InChI=1S/C9H16N4O4/c1-9(2,3)17-8(16)11-5-4-6(7(14)15)12-13-10/h6H,4-5H2,1-3H3,(H,11,16)(H,14,15)/t6-/m1/s1

InChIKey

JLMWKZYQNHSSAD-ZCFIWIBFSA-N

N3-D-Dab(Boc)-OH, a derivative of N3-Dab (3-amino-1,4-diaminobutane) with a Boc (tert-butoxycarbonyl) protecting group, is a crucial building block in the synthesis of peptides, peptide-based therapeutics, and bioactive molecules. The presence of the Boc group allows selective protection of the amino functionality during peptide synthesis, facilitating the controlled addition of amino acids to growing peptide chains. N3-D-Dab(Boc)-OH is essential in the design and development of complex peptides and conjugates, particularly those targeting specific diseases or biological pathways.

One of the primary applications of N3-D-Dab(Boc)-OH is in peptide synthesis, where it serves as an important intermediate for incorporating the D-Dab residue into peptides. D-amino acids, such as D-Dab, are used in peptide synthesis to enhance stability, prevent enzymatic degradation, and alter the conformation of the peptides. The Boc group protects the amino group during synthesis, ensuring efficient peptide elongation without unwanted side reactions. This property makes N3-D-Dab(Boc)-OH a valuable tool in producing stable and biologically active peptides for therapeutic applications, including antimicrobial, anticancer, and hormone-like peptides.

N3-D-Dab(Boc)-OH is also employed in the design of peptide conjugates, where it can be used to attach peptides to various bioactive molecules such as drugs, targeting ligands, or diagnostic agents. The D-Dab unit plays a crucial role in improving the pharmacokinetics and targeting properties of the conjugates. By linking peptides to small molecules or antibodies, researchers can create conjugates with enhanced specificity, reduced toxicity, and improved delivery efficiency. This application is particularly valuable in the development of targeted therapies, such as antibody-drug conjugates (ADCs) or peptide-drug conjugates (PDCs), for cancer or other diseases.

Another significant application of N3-D-Dab(Boc)-OH is in the creation of peptide mimetics. By incorporating the D-Dab unit into small molecule scaffolds or cyclic peptides, researchers can design compounds that mimic the biological activity of natural peptides but with improved pharmacological properties. N3-D-Dab(Boc)-OH is an ideal precursor for these peptide mimetics, which are often used in drug discovery to develop potent inhibitors of protein-protein interactions, enzymes, or receptors. This application extends the versatility of N3-D-Dab(Boc)-OH in pharmaceutical research and development.

In addition, N3-D-Dab(Boc)-OH is employed in the synthesis of functionalized materials, such as bioactive polymers and hydrogels, for drug delivery applications. The D-Dab residue provides a unique functional group that can be used for conjugation or crosslinking, while the Boc group ensures that the amine group is protected during the polymerization process. These functionalized materials are designed for controlled drug release, tissue targeting, and bioresponsive drug delivery, making N3-D-Dab(Boc)-OH an important tool in the development of advanced drug delivery systems and biomedical materials.