150629-67-7

Basic information

• Product Name: Fmoc-L-Lys(Dde)-OH
• Synonyms: FMOC-L-LYS(DDE);FMOC-L-LYS(DDE)-OH;FMOC-LYSINE(DDE)-OH;FMOC-LYS(DDE)-OH;FMOC-N-EPSILON-1-(4,4-DIMETHYL-2,6-DIOXOCYCLOHEX-1-YLIDENE)ETHYL-D-LYSINE;(S)-2-((((9H-fluoren-9-yl)Methoxy)carbonyl)aMino)-6-((1-(4,4-diMethyl-2,6-dioxocyclohexylidene)ethyl)aMino)hexanoic acid;N-Fmoc-N'-[1-(4,4-Dimethyl-2,6-dioxocyclohexylidene)ethyl]-L-lysine;Nα-Fmoc-Nω-Dde-L-lysine
• CAS NO: 150629-67-7
• Molecular Formula: C₃₁H₃₆N₂O₆
• Molecular Weight: 532.63
• Product Categories: Amino Acids;Fmoc-Amino Acids and Derivatives;amino acid
• Mol File: 150629-67-7.mol
• Article Data: 7

Chemical Properties

• Melting Point: ~80 °C (dec.)
• Boiling Point: 750.1±60.0 °C(Predicted)
• Appearance: /
• Density: 1.222±0.06 g/cm3(Predicted)
• Storage Temp.: −20°C
• Solubility: soluble in Methanol
• PKA: 3.88±0.21(Predicted)
• CAS DataBase Reference: Fmoc-L-Lys(Dde)-OH(CAS DataBase Reference)
• NIST Chemistry Reference: Fmoc-L-Lys(Dde)-OH(150629-67-7)
• EPA Substance Registry System: Fmoc-L-Lys(Dde)-OH(150629-67-7)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 150629-67-7(Hazardous Substances Data)

Usage

Description

Fmoc-L-Lys(Dde)-OH is a synthetic compound used in the field of peptide synthesis. It is a derivative of the amino acid L-lysine, with the Fmoc (9-fluorenylmethoxycarbonyl) protecting group attached to the amino group and the Dde (1,1-dimethyl-2,2,2-trichloroethyl) protecting group attached to the side chain. Fmoc-L-Lys(Dde)-OH is characterized by its white to off-white crystalline powder appearance.

Uses

Used in Peptide Synthesis:
Fmoc-L-Lys(Dde)-OH is used as an amino acid building block for the synthesis of peptides and proteins. The application reason is that it allows for the orthogonal protection of the amino group and the side chain, enabling the extension from lysine side chains using Fmoc-tBu solid-phase methodologies. This orthogonal protection is crucial for the stepwise assembly of complex peptide structures without interference from other functional groups.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Fmoc-L-Lys(Dde)-OH is used as a key component in the development of novel drug candidates. The application reason is its ability to facilitate the synthesis of specific peptide-based drugs with potential therapeutic applications, such as antibiotics, antivirals, and anticancer agents.
Used in Research and Development:
Fmoc-L-Lys(Dde)-OH is also utilized in research and development for the study of protein structure, function, and interactions. The application reason is its role in the synthesis of custom peptides and protein analogs, which can be used to investigate various biological processes and develop new therapeutic strategies.

Upstream product

• 94142-97-9 2-(1-hydroxyethylidene)-5,5-dimethylcyclohexane-1,3-dione 
• 105047-45-8 Fmoc-Lys-OH 
• 71989-26-9 Fmoc-Lys(tert-butoxycarbonyl) 
• 126-81-8 dimedone 
• 139262-23-0 α-Fmoc-L-lysine hydrochloride 
• 1755-15-3 2-acetyldimedone 

Downstream Products

• 680622-83-7 {1-{2-[2-(2-{2-[4-(2-amino-9H-purin-6-yloxymethyl)-benzyloxy]-ethoxy}-ethoxy)-ethoxy]-ethylcarbamoyl}-5-[1-(4,4-dimethyl-2,6-dioxo-cyclohexylidene)-ethylamino]-pentyl}-carbamic acid 9H-fluoren-9-ylmethyl ester 

Relevant articles and documents

A Novel Lysine-protecting Procedure for Continuous Flow Solid Phase Synthesis of Branched Peptides

A new amine protecting group which can be used orthogonally with both Fmoc and Boc protection is reported; by employing lysine protected appropriately as the branching motif, a 34 residue di-epitopic peptide has been constructed by continuous flow solid phase peptide synthesis.

Activation of lysine-specific demethylase 1 inhibitor peptide by redox-controlled cleavage of a traceless linker

We have previously employed cyclization of a linear peptide as a strategy to modulate peptide function and properties, but cleavage to regenerate the linear peptide left parts of the linker structure on the peptide, interfering with its activity. Here, we focused on cyclization of a linear peptide via a “traceless” disulfide-based linkage that would be cleaved and completely removed in a reducing environment, regenerating the original linear peptide without any linker-related structure. Thus, the linker would serve as a redox switch that would be activated in the intracellular environment. We applied this strategy to a lysine-specific demethylase 1 (LSD1) inhibitor peptide 1. The resulting cyclic peptide 2 exhibited approximately 20 times weaker LSD1-inhibitory activity than peptide 1. Upon addition of reducing reagent, the linker was completely removed to regenerate the linear peptide 1, with full restoration of the LSD1-inhibitory activity. In addition, the cyclic peptide was far less susceptible to proteolysis than the linear counterpart. Thus, this switch design not only enables control of functional activity, but also improves stability. This approach should be applicable to a wide range of peptides, and may be useful in the development of peptide pharmaceuticals.

OPTICAL IMAGING PROBES

The present invention relates to methods of visualising cells especially although not exclusively in vivo using a dye, such as a dendrimer-dye molecule or polybranched-dye molecule which is internalised by the cells and thus permits subsequent visualisation by confocal fluorescence endomicroscopy or other optical detectors. There is also provided internally quenched probes for use in visualising cells especially although not exclusively in vivo by confocal fluorescence endomicroscopy and the use of internally quenched probes in combination with confocal fluorescence endomicroscopy, for visualising cells by virtue of internalisation and dequenching of a probe by the cells. In a particular embodiment the cells are activated neutrophils, such as within the lung of a subject.