113231-04-2

Basic information

• Product Name: N6-Carbobenzyloxy-N2,N2-bis(carboxymethyl)-L-lysine
• Synonyms: N6-Carbobenzyloxy-N2,N2-bis(carboxymethyl)-L-lysine;N2,N2-Bis(carboxyMethyl)-N6-[(phenylMethoxy)carbonyl]-
• CAS NO: 113231-04-2
• Molecular Formula: C₁₈H₂₄N₂O₈
• Molecular Weight: 396.39176
• Product Categories: Amino Acids & Derivatives;Aromatics;Amino Acids & Derivatives, Aromatics
• Mol File: 113231-04-2.mol

Chemical Properties

• Melting Point: 173-175°C
• Boiling Point: 692.2±55.0 °C(Predicted)
• Appearance: /
• Density: 1.361±0.06 g/cm3(Predicted)
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility: DMSO, Methanol
• PKA: 1.67±0.10(Predicted)
• CAS DataBase Reference: N6-Carbobenzyloxy-N2,N2-bis(carboxymethyl)-L-lysine(CAS DataBase Reference)
• NIST Chemistry Reference: N6-Carbobenzyloxy-N2,N2-bis(carboxymethyl)-L-lysine(113231-04-2)
• EPA Substance Registry System: N6-Carbobenzyloxy-N2,N2-bis(carboxymethyl)-L-lysine(113231-04-2)

Safety Data

• Hazardous Substances Data: 113231-04-2(Hazardous Substances Data)

Usage

Uses

Used in Biochemistry and Molecular Biology:
N6-Carbobenzyloxy-N2,N2-bis(carboxymethyl)-L-lysine is used as a building block for the synthesis of nickel-chelating fluorinated lipids, which are essential in protein monolayer crystallizations. These lipids facilitate the study of protein structures and interactions at the molecular level, contributing to a better understanding of biological processes and the development of new therapeutic strategies.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, N6-Carbobenzyloxy-N2,N2-bis(carboxymethyl)-L-lysine is used as a key component in the development of novel drug delivery systems. Its ability to chelate nickel ions can be exploited to improve the targeting and release of therapeutic agents, potentially enhancing the efficacy and safety of various medications.
Used in Material Science:
N6-Carbobenzyloxy-N2,N2-bis(carboxymethyl)-L-lysine's unique chemical properties also make it a candidate for the development of new materials with specific applications in areas such as sensors, catalysts, and advanced coatings.

Upstream product

• 79-08-3 bromoacetic acid 
• 25528-43-2 Nε-carbobenzoxy-L-lysine hydrochloride 
• 1155-64-2 N₆-[(benzyloxy)carbonyl]-L-lysine 
• 501-53-1 benzyl chloroformate 
• 113231-05-3 N,N-bis(carboxymethyl)-L-lysine 
• 63628-63-7 Nε-benzyloxycarbonyl-L-lysine tert-butyl ester 
• 205379-07-3 N^α,N^α-bis[(tert-butyloxycarbonyl)methyl]-N^ε-benzyloxycarbonyl-L-lysine tert-butyl ester 

Downstream Products

• 1279699-68-1 ε-benzyloxycarbonyl-α-dicarboxylmethyl-L-lysine-tris(aminohexyl-β-N-acetylgalactosamine) 
• 1279699-67-0 C₇₂H₁₂₃N₅O₃₈ 
• 1309463-33-9 Z-DCM-Lys(G-ah-GalNAc)₃  
• 288318-19-4 6-benzyloxycarbonylamino-2-[bis-(2-trimethylsilanyl-ethoxycarbonylmethyl)-amino]-hexanoic acid 2-trimethylsilanyl-ethyl ester 
• 113231-05-3 N,N-bis(carboxymethyl)-L-lysine 
• 225114-88-5 methyl (2S)-6-{[(benzyloxy)carbonyl]amino}-2-[bis(2-methoxy-2-oxoethyl)amino] hexanoate 

Relevant articles and documents

Metal affinity capture tandem mass spectrometry for the selective detection of phosphopeptides

We report a new method called metal affinity capture that when coupled with tandem mass spectromery (MAC-MSMS) allows for the selective detection and identification of phosphopeptides in complex mixtures. Phosphopeptides are captured as ternary complexes with GaIII or FeIII and Nα,Nα-bis(carboxymethyl)lysme (LysNTA) in solution and electrosprayed as doubly or triply charged positive ions. The gas-phase complexes uniformly dissociate to produce a common (LysNTA + H) + ion that is used as a specific marker in precursor ion scans. The advantages of MAC-MSMS over the current methods of phosphopeptide detection are as follows. (1) MAC-MSMS uses metal complexes that self-assemble in solution at pH 69Ga-71Ga isotope pattern for selective recognition in mixtures. Detection by MAC-MSMS of singly and multiply phosphorylated peptides in tryptic digests is demonstrated at low-nanomolar protein concentrations.

Assembly of nanoparticle-protein binding complexes: From monomers to ordered arrays

(Figure Presented) Tag it: Well-defined monomers, dimers, trimers, three-dimensional spherical shells, and two-dimensional ordered arrays of genetically engineered proteins were constructed by using functionalized gold nanoparticles. Nanoparticle size, fu

Supramolecular self-assembly of amphiphiles on carbon nanotubes: A versatile strategy for the construction of CNT/metal nanohybrids, application to electrocatalysis

Homogeneous coating of carbon nanotubes with metallic nanoparticles was achieved using supramolecular auto-organization of amphiphilic molecules as template. The resulting Pd nanoparticles/carbon nanotube nanohybrids were then evaluated in electrocatalysis experiments, showing superior activity in ethanol oxidation compared to analogous systems. Copyright

Gold nanoparticle size controlled by polymeric Au(I) thiolate precursor size

We developed a method in preparing size-controllable gold nanoparticles (Au NPs, 2-6 nm) capped with glutathione by varying the pH (between 5.5 and 8.0) of the solution before reduction. This method is based on the formation of polymeric nanoparticle precursors, Au(I)-glutathione polymers, which change size and density depending on the pH. Dynamic light scattering, size exclusion chromatography, and UV-vis spectroscopy results suggest that lower pH values favor larger and denser polymeric precursors and higher pH values favor smaller and less dense precursors. Consequently, the larger precursors led to the formation of larger Au NPs, whereas smaller precursors led to the formation of smaller Au NPs. Using this strategy, Au NPs functionalized with nickel(II) nitriloacetate (Ni-NTA) group were prepared by a mixed-ligand approach. These Ni-NTA functionalized Au NPs exhibited specific binding to 6x-histidine-tagged Adenovirus serotype 12 knob proteins, demonstrating their utility in biomolecular labeling applications.

Effect of N-acetylgalactosamine ligand valency on targeting dendrimers to hepatic cancer cells

The display of N-acetylgalactosamine (NAcGal) ligands has shown great potential in improving the targeting of various therapeutic molecules to hepatocellular carcinoma (HCC), a severe disease whose clinical treatment is severely hindered by limitations in delivery of therapeutic cargo. We previously used the display of NAcGal on generation 5 (G5) polyamidoamine (PAMAM) dendrimers connected through a poly(ethylene glycol) (PEG) brush (i.e. G5-cPEG-NAcGal; monoGal) to effectively target hepatic cancer cells and deliver a loaded therapeutic cargo. In this study, we were interested to see if tri-valent NAcGal ligands (i.e. NAcGal3) displayed on G5 dendrimers (i.e. G5-cPEG-NAcGal3; triGal) could improve their ability to target hepatic cancer cells compared to their monoGal counterparts. We therefore synthesized a library of triGal particles, with either 2, 4, 6, 8, 11, or 14 targeting branches (i.e. cPEG-NAcGal3) attached. Conventional flow cytometry studies showed that all particle formulations can label hepatic cancer cells in a concentration-dependent manner, reaching 90–100% of cells labeled at either 285 or 570 nM G5, but interestingly, monoGal labeled more cells at lower concentrations. To elucidate the difference in internalization of monoGal versus triGal conjugates, we turned to multi-spectral imaging flow cytometry and quantified the amount of internalized (I) versus surface-bound (I0) conjugates to determine the ratio of internalization (I/I0) in all treatment groups. Results show that regardless of NAcGal valency, or the density of targeting branches, all particles achieve full internalization and diffuse localization throughout the cell (I/I0 ～ 3.0 for all particle compositions). This indicates that while tri-valent NAcGal is a promising technique for targeting nanoparticles to hepatic cancer cells, mono-valent NAcGal is more efficient, contrary to what is observed with small molecules.

Enhanced drug loading in polymerized micellar cargo

A new drug carrier system based on self-assembly and polymerization of polydiacetylenic amphiphiles is described. Although classical amphiphiles can help in solubilizing hydrophobic molecules upon self-arrangement into a variety of nanometric structures, a greater effect on drug loading was observed for our polymerized micelles as compared to the non-polymerized analogues. This permitted higher aqueous solubilization of lipophilic drugs with low micelle concentration. 14C labeling of a model drug on one side and of the amphiphile on the other side permitted assessment, after intravenous injection, of biodistribution and excretion profiles of the drug cargo.

Selective two-step labeling of proteins with an off/on fluorescent probe

We present a novel design strategy for off/on fluorescent probes suitable for selective two-step labeling of proteins. To validate this strategy, we designed and synthesized an off/on fluorescent probe, 1-Ni2+, which targets a cysteine-modified hexahistidine (His) tag. The probe consists of dichlorofluorescein conjugated with nitrilotriacetic acid (NTA)-Ni2+ as the His-tag recognition site and a 2,4-dinitrophenyl ether moiety, which quenches the probe's fluorescence by photoinduced electron transfer (PeT) from the excited fluorophore to the 2,4-dinitrophenyl ether (donor-excited PeT; d-PeT) and also has reactivity with cysteine. His-tag recognition by the NTA-Ni2+ moiety is followed by removal of the 2,4-dinitrophenyl ether quencher by proximity-enhanced reaction with the cysteine residue of the modified tag; this results in a marked fluorescence increase. Addition of His-tag peptide bearing a cysteine residue to aqueous probe solution resulted in about 20-fold fluorescence increment within 10 min, which is the largest fluorescence enhancement so far obtained with a visible light-excitable fluorescent probe for a His-based peptide tag. Further, we successfully visualized CysHis6-peptide tethered to microbeads without any washing step. The probe also showed a large fluorescence increment in the presence of His6Cys-tagged enhanced blue fluorescent protein (EBFP), but not His6-tagged EBFP. We consider this system is superior to large fluorescence tags (e.g., green fluorescent protein: 27 kDa), which can perturb protein folding, trafficking and function, and also to existing small tags, which generally show little fluorescence increase upon target recognition and therefore require a washout step. This strategy should also be applicable to other tags.

Multifunctional polymer micelle for jointly conveying chemotherapeutic drugs and gene editing systems as well as preparation method and application thereof (by machine translation)

The outer layer of the multifunctional polymer micelle with the three-layer structure, core as a hydrophobic polycaprolactone, inner layer is, and the outer layer of the multifunctional polymer micelle which can be coupled with a gene editing system adopts a layer of three layers and can form a shielding layer NTA, through an intermediate layer click reaction to form a shielding layer. DBCO - PEG20k - DBCO, The, invention discloses a multifunctional polymer micelle which can, be coupled DBCO - PEG with a gene editing system and a preparation method and application of the multifunctional polymer micelle. 20k - DBDBDBCO, the drug and gene editing system, protecting the inner layer load simultaneously have a targeting effect; which can efficiently enter the tumor cell, as the carrier, and enter the lysosome, and then release the chemotherapeutic drug and the gene editing system, to act, together to ensure, no drug resistance of tumor cells is enhanced, at the same time in the case, of chemotherapy drug dosage . (by machine translation)

The Scaffold Design of Trivalent Chelator Heads Dictates Affinity and Stability for Labeling His-tagged Proteins in vitro and in Cells

Small chemical/biological interaction pairs are at the forefront in tracing protein function and interaction at high signal-to-background ratios in cellular pathways. However, the optimal design of scaffold, linker, and chelator head still deserve systematic investigation to achieve the highest affinity and kinetic stability for in vitro and especially cellular applications. We report on a library of N-nitrilotriacetic acid (NTA)-based multivalent chelator heads (MCHs) built on linear, cyclic, and dendritic scaffolds and compare these with regard to their binding affinity and stability for the labeling of cellular His-tagged proteins. Furthermore, we describe a new approach for tracing cellular target proteins at picomolar probe concentrations in cells. Finally, we outline fundamental differences between the MCH scaffolds and define a cyclic trisNTA chelator that displays the highest affinity and kinetic stability of all reported reversible, low-molecular-weight interaction pairs.

Chelating agent, synthesis method and application thereof as well as chelate containing the same

The invention discloses a chelating agent, which has a structural general formula shown as the specification. The invention also discloses a chelate containing the chelating agent and metal ions, and a synthesis method of the chelating agent. The method includes: (1) synthesizing a precursor compound of the chelating agent by active ester method; (2) carrying out catalytic hydrogenation reaction to obtain the chelating agent. The chelating agent can be used as a radioactive imaging and therapy drug, a magnetic resonance imaging drug, selective chelation separate trivalent metal ions and the like. The chelating agent provided by the invention is a hexadentate ligand, has strong chelating ability with a lot of trivalent metal ions, and therefore has small dosage during chelate formation, and has reduced toxic and side effect when serving as a drugs, at the same time the chelating agent contains amino at the left end and can achieve connection with some biological target molecules, and can be used for preparation of various targeted drugs. The coordination reaction of the chelating agent and metal ions has mild conditions (usually at room temperature), and the drug preparation process is simplified. The preparation method of the chelating agent has the advantages of easily available raw materials and simple process, thus being easy for large-scale promotion.