Name: Boc-ε-azido-Nle-OH
Brand: BOC Sciences
Rating: 5 (1 reviews)

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Synonyms

Boc-Lys(N3)-OH; N-α-t-Butyloxycarbonyl-epsilon-azido-L-lysine; N-α-t-Butyloxycarbonyl-epsilon-azido-L-norleucine; (S)-2-t-Butyloxycarbonylamino-6-azidohexanoic acid; 6-Azido-N-Boc-L-Norleucine; (S)-6-azido-2-(Boc-amino)hexanoic acid; Boc-6-azido-L-norleucine; Nα-Boc-Nε-Azido-L-Lysine; N-tert-butoxycarbonyl-6-azido-L-norleucine

IUPAC Name

(2S)-6-azido-2-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoic acid

Canonical SMILES

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

InChI

InChI=1S/C11H20N4O4/c1-11(2,3)19-10(18)14-8(9(16)17)6-4-5-7-13-15-12/h8H,4-7H2,1-3H3,(H,14,18)(H,16,17)/t8-/m0/s1

InChIKey

SKRPDWWWUARZIW-QMMMGPOBSA-N

Solubility

Soluble in Methanol

Appearance

White Powder

Storage

Store at -20°C

Boc-ε-azido-Nle-OH is a chemical compound, recognized for its role as a building block in peptide synthesis. This compound features an N-terminal Boc (tert-butoxycarbonyl) protecting group and an azide functional group, which is of particular interest due to its reactivity.

One critical application of Boc-ε-azido-Nle-OH is in the field of peptide engineering. Peptide synthesis often leverages such reagents to introduce azido functionalities into peptide chains, which can be subsequently modified through click chemistry. This allows for the attachment of various molecular entities, such as fluorescent dyes or drug molecules, facilitating the development of multifunctional peptides. These modified peptides can be utilized in research for imaging applications, therapeutic delivery systems, and as molecular probes, furthering our understanding of biological processes and aiding in the development of new therapies.

Another significant utilization of Boc-ε-azido-Nle-OH lies in drug delivery system innovations. The azido group can serve as a handle for the conjugation of pharmaceutical compounds to peptides, forming bioconjugates that improve the delivery and efficacy of drugs. By attaching therapeutic agents to peptides, drug solubility, stability, and specificity can be enhanced. This leads to greater bioavailability and targeted delivery to diseased tissues or cells, minimizing side effects and improving patient outcomes in treatments such as targeted cancer therapy.

Boc-ε-azido-Nle-OH is also instrumental in creating peptide-based diagnostics. The azide group enables the incorporation of diagnostic markers that can bind to specific biomolecules or cell types. In clinical diagnostics, these linked markers can help in the early detection of diseases through imaging or analytical techniques, offering a non-invasive means of monitoring health conditions. The specificity and versatility of peptide markers make them invaluable tools in personalized medicine, where they aid in tailoring diagnostic and treatment strategies to individual patients.

Lastly, Boc-ε-azido-Nle-OH is employed in the synthesis of novel materials for research and industrial applications. The ability to form strong covalent bonds with a variety of substrates via click chemistry means that peptides containing azido groups can be used in the development of biocompatible materials, hydrogels, and nanoparticle coatings. These materials have wide-ranging applications, from wound healing dressings to components in biosensors, showcasing the compound’s utility beyond the confines of traditional biochemistry into the realms of advanced material science and engineering.