Name: Fmoc-L-Lys(4-N3-Z)-OH
Brand: BOC Sciences
Rating: 5 (1 reviews)

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Synonyms

(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-6-((((4-azidobenzyl)oxy)carbonyl)amino)hexanoic acid

IUPAC Name

(2S)-6-[(4-azidophenyl)methoxycarbonylamino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)hexanoic acid

Canonical SMILES

C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CCCCNC(=O)OCC4=CC=C(C=C4)N=[N+]=[N-])C(=O)O

InChI

InChI=1S/C29H29N5O6/c30-34-33-20-14-12-19(13-15-20)17-39-28(37)31-16-6-5-11-26(27(35)36)32-29(38)40-18-25-23-9-3-1-7-21(23)22-8-2-4-10-24(22)25/h1-4,7-10,12-15,25-26H,5-6,11,16-18H2,(H,31,37)(H,32,38)(H,35,36)/t26-/m0/s1

InChIKey

RSWJAKDWNDKFAB-SANMLTNESA-N

Fmoc-L-Lys(4-N3-Z)-OH, a specialized reagent utilized in peptide synthesis and bioconjugation studies, possesses diverse applications in the realm of chemical biology. Here are four key applications:

Peptide Synthesis: Serving as a fundamental component in solid-phase peptide synthesis, Fmoc-L-Lys(4-N3-Z)-OH plays a pivotal role in crafting peptides with tailored functionalities for varied research and therapeutic purposes. The presence of an azide group enables subsequent post-synthetic functionalization through click chemistry methodologies, allowing for the creation of custom peptides with specific attributes and functionalities that cater to unique applications in the field.

Site-Specific Labeling: Leveraging the azide group inherent in Fmoc-L-Lys(4-N3-Z)-OH, researchers can achieve precise and targeted labeling of peptides and proteins through bioorthogonal click reactions, such as the azide-alkyne cycloaddition. This innovative approach facilitates the attachment of fluorescent tags, probes, or other biomolecules to peptides and proteins, enabling the exploration of intricate protein interactions and dynamics with a high level of specificity and accuracy.

Bioconjugation: In the realm of bioconjugation techniques, Fmoc-L-Lys(4-N3-Z)-OH facilitates the covalent linking of proteins and biomolecules through the versatile azide functionality. This feature serves as a convenient handle for conjugating a diverse array of molecules, including drugs, nanoparticles, and polymers, thereby playing a crucial role in the development of targeted drug delivery systems and advanced biomaterials that hold potential for groundbreaking advances in the field of biomedicine.

Chemical Biology: The azide-protected lysine derivative offers a gateway to introducing azide functionalities into peptides and proteins, enabling their utilization in chemical biology applications. These azide-modified biomolecules can actively engage in click chemistry reactions, shedding light on protein functions and interactions within the intricate cellular milieu.