1257063-35-6

Basic information

• Product Name: 15-Azido-4,7,10,13-tetraoxapentadecanoic acid
• Synonyms: 15-Azido-4,7,10,13-tetraoxapentadecanoic acid;N3-Peg(4)-cooh;3-[2-[2-[2-(2-Azidoethoxy)ethoxy]ethoxy]ethoxy]propanoic acid;Azido-PEG4-acid;Azido-PEG5-acid;N3-PEG4-CH2CH2COOH;Azido-PEG4-propionic acid;15-Azido-4,7,10,13-tetraoxapentadecanoic acid≥ 97% (NMR)
• CAS NO: 1257063-35-6
• Molecular Formula: C₁₁H₂₁N₃O₆
• Molecular Weight: 291.30094
• Mol File: 1257063-35-6.mol
• Article Data: 3

Chemical Properties

• Appearance: Colorless to Pale Yellow/Liquid
• Storage Temp.: -20°C
• CAS DataBase Reference: 15-Azido-4,7,10,13-tetraoxapentadecanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 15-Azido-4,7,10,13-tetraoxapentadecanoic acid(1257063-35-6)
• EPA Substance Registry System: 15-Azido-4,7,10,13-tetraoxapentadecanoic acid(1257063-35-6)

Safety Data

• Hazardous Substances Data: 1257063-35-6(Hazardous Substances Data)

Usage

Description

Azido-PEG4-acid is a very popular PEG reagent containing an azide group with a terminal carboxylic acid. The hydrophilic PEG spacer increases solubility in aqueous media. The azide group can react with alkyne, BCN, DBCO via Click Chemistry to yield a stable triazole linkage. The terminal carboxylic acid can react with primary amine groups in the presence of activators (e.g. EDC, or HATU) to form a stable amide bond.

Chemical Properties

Light yellow to colorless thick liquid

Uses

Azido-PEG4-Acid is amine- or phosphine-reactive building block used to derivative primary amines for ligation to alkyne-tagged molecules.

Upstream product

• 581066-04-8 tert-butyl 1-azido-3,6,9,12-tetraoxapentadecan-15-oate 
• 112-60-7 Tetraethylene glycol 
• 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 
• 168640-82-2 11-azido-3,6,9-trioxa-undecanyl p-toluenesulfonate 

Downstream Products

• 663921-15-1 3-[2-(2-{2-[2-(2-aminoethoxy)ethoxy]ethoxy}ethoxy)ethoxy]propanoic acid 
• 1604837-41-3 C₄₇H₅₈N₇O₇⁽¹⁺⁾ 
• 1320195-00-3 C₆₃H₉₀N₁₀O₁₈ 
• 1320194-99-7 benzyl 15-azido(4,7,10,13)tetraoxapentadecanoate 
• 1337909-86-0 C₃₅H₃₉N₆O₈P 
• 1337909-89-3 C₃₀H₃₇N₆O₇PS 

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.

CRYPTOPHYCIN-BASED ANTIBODY-DRUG CONJUGATES WITH NOVEL SELF-IMMOLATIVE LINKERS

The present invention relates to antibody- or peptide-drug conjugate compounds where one or more cryptophycin derivatives (macrocyclic depsipeptide) are covalently attached by a self-immolative linker which binds to one or more tumor-associated antigens or cell-surface receptors. The linker contains a cleavage site for proteases and a dipeptide unit able to form a diketopiperazine. These compounds may be useful in methods of diagnosis or treatment of cancer, and other diseases and disorders, such as immune or infective diseases.