581065-95-4

Basic information

• Product Name: H2N-PEG4-tBu
• Synonyms: H2N-PEG4-tBu;tert-Butyl 15-aMino-4,7,10,13-tetraoxapentadecanoate;2-[2-[2-[2-(2-tert-Butoxycarbonylethoxy)ethoxy]ethoxy]ethoxy]ethylamine;H2N-PEG4-CH2CH2COOtBu;Amino-PEG4-t-butyl ester;H2N-PEG4-CH2CH2COOtBu;Amino-dPEG4-t-butyl ester;tert-Butyl 1-amino-3,6,9,12-tetraoxapentadecan-15-oate
• CAS NO: 581065-95-4
• Molecular Formula: C₁₅H₃₁NO₆
• Molecular Weight: 321.40974
• Product Categories: PEG-COOtBu
• Mol File: 581065-95-4.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 400.1±35.0 °C(Predicted)
• Appearance: /
• Density: 1.040±0.06 g/cm3(Predicted)
• Storage Temp.: -20°C
• Solubility: Soluble in Water, DMSO, DCM, DMF
• PKA: 8.74±0.10(Predicted)
• CAS DataBase Reference: H2N-PEG4-tBu(CAS DataBase Reference)
• NIST Chemistry Reference: H2N-PEG4-tBu(581065-95-4)
• EPA Substance Registry System: H2N-PEG4-tBu(581065-95-4)

Safety Data

• Hazardous Substances Data: 581065-95-4(Hazardous Substances Data)

Usage

Description

H2N-PEG4-tBu, also known as Amino-PEG4-t-butyl ester, is a PEG reagent that contains an amino (NH2) group and a t-butyl protected carboxyl group. The hydrophilic PEG spacer enhances solubility in aqueous media, while the amino group is reactive with various functional groups such as carboxylic acids, activated NHS esters, and carbonyls. The t-butyl protected carboxyl (Boc) can be deprotected under acidic conditions, making it a versatile molecule for various applications.

Uses

Used in Pharmaceutical Industry:
H2N-PEG4-tBu is used as a linker-cytotoxin conjugate for the development of antibody-cytotoxin and antibody-drug conjugates. This application takes advantage of the molecule's reactivity with various functional groups, allowing for the creation of targeted therapies that can deliver cytotoxic agents specifically to cancer cells, minimizing damage to healthy cells.
Used in Drug Delivery Systems:
In the field of drug delivery, H2N-PEG4-tBu is utilized as a component in the design and synthesis of novel drug delivery systems. The hydrophilic PEG spacer and reactive amino group enable the conjugation of drugs or imaging agents to the carrier, improving the solubility, stability, and targeted delivery of therapeutic agents.
Used in Bioconjugation:
H2N-PEG4-tBu is also used as a bioconjugation agent, facilitating the attachment of biologically active molecules, such as peptides, proteins, or nucleic acids, to various surfaces or carriers. The t-butyl protected carboxyl group allows for controlled deprotection and subsequent conjugation under mild conditions, preserving the integrity of the biomolecule.
Used in Diagnostics:
In the diagnostics industry, H2N-PEG4-tBu can be employed as a component in the development of imaging agents or biosensors. The hydrophilic PEG spacer and reactive amino group can be used to attach contrast agents or signaling moieties to biomolecules, enhancing their detection and imaging capabilities in various diagnostic applications.

Upstream product

• 581066-04-8 tert-butyl 1-azido-3,6,9,12-tetraoxapentadecan-15-oate 
• 112-60-7 Tetraethylene glycol 
• 1663-39-4 tert-Butyl acrylate 
• 518044-32-1 tert-butyl 3-(2-{2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)propanoate 
• 581065-94-3 tert-butyl 3-[2-(2-{2-[2-(toluene-4-sulfonyloxy)-ethoxy]ethoxy}ethoxy)ethoxy]propionate 
• 870487-48-2 tert-butyl 1-(methanesulfonyloxy)-3,6,9,12-tetraoxapentadecan-15-oate 
• 77544-60-6 p-toluenesulfonic acid 2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethyl ester 
• 86770-67-4 2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethanol 

Downstream Products

• 960215-56-9 1-{1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl}-2-oxo-6,9,12,15-tetraoxa-3-azaoctadecan-18-oic acid 
• 870487-58-4 C₂₅H₄₂N₂O₇S₂ 
• 1415329-56-4 C₂HF₃O₂*C₅₅H₉₆N₆O₁₃ 
• 1426164-52-4 MAL-Lys(MAL)-dPEG₄-acid 
• 1426164-53-5 bis-maleimide-lysine-PEG₄-TFP 
• 1426164-58-0 MAL-dPEG₂-Lys(MAL-dPEG₂)-dPEG₄-TFP 
• 1426164-49-9 tert-butyl (S)-9-(((benzyloxy)carbonyl)amino)-3,10-dioxo-1-phenyl-2,14,17,20,23-pentaoxa-4,11-diazahexacosan-26-oate 
• 663921-15-1 3-[2-(2-{2-[2-(2-aminoethoxy)ethoxy]ethoxy}ethoxy)ethoxy]propanoic acid 

Relevant articles and documents

Optimization of IEDDA bioorthogonal system: Efficient process to improve trans-cyclooctene/tetrazine interaction

The antibody pretargeting approach for radioimmunotherapy (RIT) using inverse electron demand Diels-Alder cycloaddition (IEDDA) constitutes an emerging theranostic approach for solid cancers. However, IEDDA pretargeting has not reached clinical trial. The major limitation of the IEDDA strategy depends largely on trans-cyclooctene (TCO) stability. Indeed, TCO may isomerize into the more stable but unreactive cis-cyclooctene (CCO), leading to a drastic decrease of IEDDA efficiency. We have thus developed both efficient and reproducible synthetic pathways and analytical follow up for (PEGylated) TCO derivatives, providing high TCO isomeric purity for antibody modification. We have set up an original process to limit the isomerization of TCO to CCO before the mAbs’ functionalization to allow high TCO/tetrazine cycloaddition.

Preparation method of amino polyethylene glycol propionic acid

The invention relates to the field of organic synthesis, in particular to a preparation method of amino polyethylene glycol propionic acid. The preparation method comprises the steps that catalytic hydrogenation is carried out on dibenzyl amino polyethylene glycol tert-butyl propionate shown in formula I-2 to obtain amino polyethylene glycol tert-butyl propionate shown in formula I-3; (2) the amino polyethylene glycol tert-butyl propionate shown in formula I-3 is hydrolyzed under the acidic condition to obtain amino polyethylene glycol propionic acid shown in formula I. The preparation methodof the amino polyethylene glycol propionic acid has the advantages that the defects in the prior art that the yield is low, the dangerousness is high, and the enlargement of production is difficult are overcome, the reaction conditions are mild, the operation is simple, an intermediate does not to be purified, the next reaction can be directly carried out, the whole yield reaches up to 87-92%, thepurity of end products reaches up to 97-99.5%, and a safe and efficient synthetic route is provided for the preparation of amino polyethylene glycol propionic acid.

OPTIMIZED TRANSGLUTAMINASE SITE-SPECIFIC ANTIBODY CONJUGATION

Provided herein are methods and compositions for site-specific conjugation of antibodies.