O-(2-(2-(2-(Prop-2-yn-1-yloxy)ethoxy)ethoxy)ethyl)hydroxylamine | CAS 1807537-27-4

O-(2-(2-(2-(Prop-2-yn-1-yloxy)ethoxy)ethoxy)ethyl)hydroxylamine is a hydroxylamine-functionalized alkyne click chemistry reagent designed for bioorthogonal conjugation workflows. Its structure combines a terminal propargyl ether motif for Cu(I)-catalyzed azide–alkyne cycloaddition compatibility with a hydroxylamine handle that can be leveraged to build stable oxime-linked constructs or to support orthogonal labeling strategies in complex chemical biology experiments. This reagent is commonly selected when researchers need robust, flexible linkers that improve solubility and reduce steric constraints during probe, polymer, and biomolecule functionalization.

1. Oxime-Based Probe Conjugation

O-(2-(2-(2-(Prop-2-yn-1-yloxy)ethoxy)ethoxy)ethyl)hydroxylamine is used to generate oxime-linked probe conjugates where a hydroxylamine functionality is required to couple to carbonyl-bearing partners such as aldehyde-functional biomolecules, glycan-modified targets, or oxidized biomaterial surfaces. The inclusion of the propargyl ether provides a convenient downstream click handle, enabling sequential functionalization workflows that are popular in chemical biology and imaging reagent development. Researchers often choose this reagent to create multi-component labeling reagents that can be attached to a primary targeting or recognition scaffold and then extended with reporter tags, affinity groups, or purification-compatible moieties.

2. Molecular Imaging Labeling Platforms

O-(2-(2-(2-(Prop-2-yn-1-yloxy)ethoxy)ethoxy)ethyl)hydroxylamine supports the construction of imaging and detection platforms that rely on modular, orthogonal labeling. The reagent’s alkyne functionality is frequently incorporated into probe design so that, after initial oxime coupling to an aldehyde-containing biomolecule or material, the resulting conjugate can be further decorated via click chemistry to install fluorophores, affinity handles, or other signal reporters. Flexible poly(ethylene glycol)-like spacing in the linker region helps maintain accessibility of the functional groups, which is valuable when preparing imaging reagents for microscopy workflows, labeled binding assays, or multiplexed detection toolkits used in research laboratories.

3. Biomaterials Surface Functionalization

O-(2-(2-(2-(Prop-2-yn-1-yloxy)ethoxy)ethoxy)ethyl)hydroxylamine is applied to functionalize biomaterial surfaces and polymeric scaffolds where hydroxylamine chemistry provides a practical route to immobilize reactive components onto aldehyde-activated coatings. Once anchored, the retained alkyne handle enables subsequent click-based attachment of secondary components such as fluorescent labels, affinity ligands, or bioactive motifs used for material characterization and surface reactivity studies. This approach is widely adopted in biomaterials science because it allows stepwise assembly of multifunctional surfaces while using linkers that can improve wettability, reduce non-specific interactions, and preserve accessibility for later conjugation steps.

4. Targeted Chemical Biology Tooling

O-(2-(2-(2-(Prop-2-yn-1-yloxy)ethoxy)ethoxy)ethyl)hydroxylamine is frequently incorporated into targeted chemical biology tooling where researchers need a reliable conjugation intermediate that can connect diverse biomolecular building blocks. The hydroxylamine functionality supports oxime formation with carbonyl-containing partners, while the propargyl ether provides a click-compatible handle for attaching reporters or enrichment reagents. This dual-handle design is particularly useful for creating modular labeling reagents used in pathway mapping, protein/material interaction studies, and affinity-based pull-down workflows that benefit from sequential assembly and orthogonal labeling control.