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

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Synonyms

N-alpha-(9-Fluorenylmethyloxycarbonyl)-N-epsilon-[6-azido-1-(4,4-dimethyl-2,6-dioxocyclohexylidene)hexyl]-L-lysine

IUPAC Name

(2S)-6-[[6-azido-1-(2-hydroxy-4,4-dimethyl-6-oxocyclohexen-1-yl)hexylidene]amino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)hexanoic acid

Canonical SMILES

CC1(CC(=C(C(=O)C1)C(=NCCCCC(C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24)CCCCCN=[N+]=[N-])O)C

InChI

InChI=1S/C35H43N5O6/c1-35(2)20-30(41)32(31(42)21-35)28(16-4-3-10-19-38-40-36)37-18-11-9-17-29(33(43)44)39-34(45)46-22-27-25-14-7-5-12-23(25)24-13-6-8-15-26(24)27/h5-8,12-15,27,29,41H,3-4,9-11,16-22H2,1-2H3,(H,39,45)(H,43,44)/t29-/m0/s1

InChIKey

BFEOBKQXWBSIEV-LJAQVGFWSA-N

Fmoc-L-Lys(N3-Aca-DIM)-OH is a specialized amino acid derivative used in peptide synthesis and other advanced biochemical applications. Here are some key applications of Fmoc-L-Lys(N3-Aca-DIM)-OH:

Peptide Synthesis: Fmoc-L-Lys(N3-Aca-DIM)-OH is utilized in solid-phase peptide synthesis to introduce lysine residues with specific functional groups. This allows for the design and synthesis of custom peptides with unique properties such as enhanced binding affinity or stability. Such peptides are valuable in drug development, structural biology, and therapeutic research.

Chemical Biology: In chemical biology, this amino acid derivative is used to create bioconjugates and modified proteins. The presence of the azido group (N3) enables bioorthogonal click chemistry reactions, allowing the attachment of various probes, tags, or other functional groups. This facilitates the tracking, imaging, and functional analysis of proteins in biological systems.

Targeted Drug Delivery: Fmoc-L-Lys(N3-Aca-DIM)-OH can be incorporated into peptide-based drug delivery systems to enhance specificity and efficacy. By conjugating therapeutic agents to peptides containing this derivative, researchers can develop targeted delivery systems that release drugs in response to specific cellular environments or stimuli. This approach improves the precision and reduces the side effects of treatments.

Antimicrobial Peptide Design: This specialized amino acid derivative is used in the design of antimicrobial peptides (AMPs) with improved activity and selectivity. By modifying the lysine residue through azido and dimethylamino groups, researchers can enhance the interaction of AMPs with microbial membranes. This leads to the development of potent and selective antimicrobial agents for treating bacterial infections.