134272-63-2

Usage

Uses

Used in Chemical Synthesis:
N-BOC-2-MALEIMIDOETHYLAMINE is used as a reagent in the Mitsunobu reaction, a novel method for the synthesis of bifunctional maleimide linkers. This application is significant because it enables the creation of new compounds with potential applications in various fields, such as pharmaceuticals, materials science, and biochemistry.
Used in Bioconjugation:
In the field of biochemistry and molecular biology, N-BOC-2-MALEIMIDOETHYLAMINE is used as a bioconjugation agent for the selective modification of cysteine residues in proteins. The maleimide group reacts specifically with thiol groups, allowing for the covalent attachment of other biomolecules, such as fluorescent tags, affinity labels, or therapeutic agents, to the protein of interest.
Used in Drug Development:
N-BOC-2-MALEIMIDOETHYLAMINE can be employed in the development of new drugs, particularly those targeting proteins with cysteine residues. By forming covalent bonds with these residues, the compound can potentially modulate protein function, leading to the development of novel therapeutic strategies.
Used in Materials Science:
In materials science, N-BOC-2-MALEIMIDOETHYLAMINE can be utilized in the synthesis of novel materials with specific properties, such as self-healing materials or stimuli-responsive polymers. The ability of the maleimide group to form covalent bonds with thiol-containing compounds can be exploited to create materials with tailored properties and functions.

Upstream product

• 541-59-3 maleiimide 
• 26690-80-2 2-(N-tert-butoxycarbonylamino)ethanol 
• 55750-48-6 N-methoxycarbonylmaleimide 
• 108-31-6 maleic anhydride 
• 57260-73-8 N-BOC-1,2-diaminoethane 
• 34619-03-9 tert-butyldicarbonate 
• 215654-55-0 C₁₁H₁₈N₂O₅ 
• 55750-49-7 N-ethoxycarbonylmaleinimide 
• 24424-99-5 di-tert-butyl dicarbonate 
• 215654-55-0 (Z)-3-(2-tert-Butoxycarbonylamino-ethylcarbamoyl)-acrylic acid 

Downstream Products

• 139554-72-6 1-(2-(D-biotinamido)ethyl)-1H-pyrrole-2,5-dione 
• 160291-45-2 5-(dimethylamino)-N-(2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethyl)naphthalene-1-sulfonamide 
• 134272-64-3 2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethanaminium chloride 
• 125923-10-6 1-(2-aminoethyl)-1H-pyrrole-2,5-dione 

Relevant academic research and scientific papers

Norborn-2-en-7-ones as physiologically-triggered carbon monoxide-releasing prodrugs

A prodrug strategy for the release of the gasotransmitter CO at physiological pH, based upon 3a-bromo-norborn-2-en-7-one Diels-Alder cycloadducts of 2-bromomaleimides and 2,5-dimethyl-3,4-diphenylcyclopentadienone has been developed. Examples possessing protonated amine and diamine groups showed good water solubility and thermal stability. Half-lives for CO-release in TRIS-sucrose buffer at pH 7.4 ranged from 19 to 75 min at 37 °C and 31 to 32 h at 4 °C. Bioavailability in rats was demonstrated by oral gavage and oCOm-21 showed a dose dependent vasorelaxant effect in pre-contracted rat aortic rings with an EC50 of 1.6 ± 0.9 μM. Increased intracellular CO levels following oCOm-21 exposure were confirmed using a CO specific fluorescent probe.

Reassessment of diethylenetriaminepentaacetic acid (DTPA) as a chelating agent for indium-111 labeling of polypeptides using a newly synthesized monoreactive DTPA derivative

Previous studies on indium-111 (111In) labeling of polypeptides and peptides using cyclic diethylenetriaminepentaacetic dianhydride (cDTPA) as a bifunctional chelating agent (BCA) have indicated that DTPA might be a useful BCA for 111/sup

Facile fabrication of fast recyclable and multiple self-healing epoxy materials through diels-alder adduct cross-linker

J. Polym. Sci., Part A: Polym. Chem. 2015, 53, 2094-2103 A reversibly cross-linked epoxy resin with efficient reprocessing and intrinsic self-healing has been prepared from a newly synthesized diamine Diels-Alder (DA) adduct cross-linker and a commercial epoxy oligomer. The methodology developed in this work takes smart and environmentally benign epoxy to the next level of simplicity and provides new insights in the modification of traditional engineering plastics as a functional material.

Controlled Covalent Functionalization of 2 H-MoS2 with Molecular or Polymeric Adlayers

Most air-stable 2D materials are relatively inert, which makes their chemical modification difficult. In particular, in the case of MoS2, the semiconducting 2 H-MoS2 is much less reactive than its metallic counterpart, 1T-MoS2. As a consequence, there are hardly any reliable methods for the covalent modification of 2 H-MoS2. An ideal method for the chemical functionalization of such materials should be both mild, not requiring the introduction of a large number of defects, and versatile, allowing for the decoration with as many different functional groups as possible. Herein, a comprehensive study on the covalent functionalization of 2 H-MoS2 with maleimides is presented. The use of a base (Et3N) leads to the in situ formation of a succinimide polymer layer, covalently connected to MoS2. In contrast, in the absence of base, functionalization stops at the molecular level. Moreover, the functionalization protocol is mild (occurs at room temperature), fast (nearly complete in 1 h), and very flexible (11 different solvents and 10 different maleimides tested). In practical terms, the procedures described here allow for the chemist to manipulate 2 H-MoS2 in a very flexible way, decorating it with polymers or molecules, and with a wide range of functional groups for subsequent modification. Conceptually, the spurious formation of an organic polymer might be general to other methods of functionalization of 2D materials, where a large excess of molecular reagents is typically used.

Lipopolysaccharide neutralizing peptide-porphyrin conjugates for effective photoinactivation and intracellular imaging of gram-negative bacteria strains

A simple and specific strategy based on the bioconjugation of a photosensitizer protophophyrin IX (PpIX) with a lipopolysaccharide (LPS) binding antimicrobial peptide YI13WF (YVLWKRKRKFCFI-Amide) has been developed for the effective fluorescent imaging an

Aldehyde-mediated bioconjugation: Via in situ generated ylides

A technically simple approach for rapid, high-yielding and site-selective bioconjugation has been developed for both in vitro and cellular applications. This method involves the generation of maleimido-phosphonium ylides via 4-nitrophenol catalysis under physiological conditions followed by their Wittig reactions with aldehyde-appended biomolecules.

Engineering Boron Hot Spots for the Site-Selective Installation of Iminoboronates on Peptide Chains

Boronic acids (BAs) are a promising bioconjugation function to design dynamic materials as they can establish reversible covalent bonds with oxygen/nitrogen nucleophiles that respond to different pH, ROS, carbohydrates and glutathione levels. However, the dynamic nature of these bonds also limits the control over the stability and site-selectivity of the bioconjugation, which ultimately leads to heterogeneous conjugates with poor stability under physiological conditions. Here we disclose a new strategy to install BAs on peptide chains. In this study, a “boron hot spot“ based on the 3-hydroxyquinolin-2(1H)-one scaffold was developed and upon installation on a peptide N-terminal cysteine, enables the site-selective formation of iminoboronates with 2-formyl-phenyl boronic acids (Ka of 58128±2 m?1). The reaction is selective in the presence of competing lysine ?-amino groups, and the resulting iminoboronates, displayed improved stability in buffers solutions and a cleavable profile in the presence of glutathione. Once developed, the methodology was used to prepare cleavable fluorescent conjugates with a laminin fragment, which enabled the validation of the 67LR receptor as a target to deliver cargo to cancer HT29 cells.

Fast and efficient [2 + 2] UV cycloaddition for polymer modification via flow synthesis

The alkene-enone [2 + 2] photocycloaddition reaction between polymer-bound maleimide and functional alkenes has been tested in a UV-flow reactor, demonstrating a very high efficiency of the reaction. As a test reaction, polymer end group modifications were carried out on maleimide-functional poly(butyl acrylate). The polymer was prepared by atom transfer radical polymerization (ATRP) using a N-hydroxysuccinimide-functionalized initiator, followed by exchange reaction of the activated ester with a maleimide amine linker. Good control over the polymerization and successful exchange of the end group under mild reaction conditions was confirmed by electrospray ionization mass spectrometry (ESI-MS). The terminal maleimide group was then reacted quantitatively with alkenes in a custom-made tubular UV-flow reactor within a minute reaction time. Compared to reaction times in batch of several hours to days, the reaction proceeds to full conversion within 1 min under flow conditions. This significant acceleration of the reaction was achieved by employing a photosensitizer in combination with the flow reactor technique. Via the cycloaddition a variety of functional groups can be introduced to the polymer chain ranging from multifunctional allyl compounds to hydroxyl-functional alkenes, demonstrating the general versatility and high potential of the approach for polymer modification reactions.

One-pot: N -glycosylation remodeling of IgG with non-natural sialylglycopeptides enables glycosite-specific and dual-payload antibody-drug conjugates

Chemoenzymatic transglycosylation catalyzed by endo-S mutants is a powerful tool for in vitro glycoengineering of therapeutic antibodies. In this paper, we report a one-pot chemoenzymatic synthesis of glycoengineered Herceptin using an egg-yolk sialylglycopeptide (SGP) substrate. Combining this one-pot strategy with novel non-natural SGP derivatives carrying azido or alkyne tags, glycosite-specific conjugation was enabled for the development of new antibody-drug conjugates (ADCs). The site-specific ADCs and semi-site-specific dual-drug ADCs were successfully achieved and characterized with SDS-PAGE, intact antibody or ADC mass spectrometry analysis, and PNGase-F digestion analysis. Cancer cell cytotoxicity assay revealed that small-molecule drug release of these ADCs relied on the cleavable Val-Cit linker fragment embedded in the structure. These results represent a new approach for glycosite-specific and dual-drug ADC design and rapid synthesis, and also provide the structural requirement for their biologic activities.

An endoplasmic reticulum-targeted organic photothermal agent for enhanced cancer therapy

Developing selectively targeted photothermal agents to reduce side effects in photothermal therapy remains a great challenge. Inspired by the key role of endoplasmic reticulum in the protein synthesis and intracellular signal transduction, particularly for the immunogenic cell death induced by endoplasmic reticulum stress, we developed an endoplasmic reticulum-targeted organic photothermal agent (Ts-PT-RGD) for enhancing photothermal therapy of tumor. The photothermal agent was covalently attached with 4-methylbenzenesulfonamide and cyclic Arg-Gly-Asp (cRGD) peptide for realizing the targeting of endoplasmic reticulum and tumor cell. Owing to its amphiphilic properties, it readily self-assembles in water to form nanoparticles. The photothermal agent possesses excellent photophysical properties and biological compatibility. In vitro and in vivo experiments demonstrate that it can actively target endoplasmic reticulum and effectively ablate tumor with near-infrared laser.