
Alkyne maleimide
| Catalog Number | R02-0006 |
| Category | Alkynes |
| Molecular Formula | C12H14N2O3 |
| Molecular Weight | 234.25 |
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Product Introduction
Alkyne maleimide is a bifunctional linker reagent which allows to attach terminal alkyne to various thiol-containing molecules, such as proteins containing cysteine residues. The alkyne moiety can be then conjugated with various azides via copper-catalyzed Click chemistry reaction.
Chemical Information
Application
Computed Properties
Patents
Chemical Information
| Purity | NMR 1H, HPLC-MS (95%) |
| IUPAC Name | N-[2-(2,5-dioxopyrrol-1-yl)ethyl]hex-5-ynamide |
| SMILES | C#CCCCC(=O)NCCN1C(=O)C=CC1=O |
| InChI | InChI=1S/C12H14N2O3/c1-2-3-4-5-10(15)13-8-9-14-11(16)6-7-12(14)17/h1,6-7H,3-5,8-9H2,(H,13,15) |
| InChIKey | JFWXHCHRKDOVRJ-UHFFFAOYSA-N |
| Solubility | good in DMSO, DMF, alcohols, limited in water |
| Appearance | colorless solid |
Application
Alkyne maleimide is a bifunctional click chemistry reagent that combines a maleimide electrophile with a terminal alkyne handle, enabling bioorthogonal conjugation to thiol-containing biomolecules followed by alkyne-based click coupling for downstream labeling and material functionalization. As a widely used platform for sequential conjugation workflows, it is commonly incorporated into probe, linker, and surface-modification strategies where controlled attachment to cysteine or other thiol groups is required. The presence of the alkyne functionality supports downstream enrichment, imaging, and construction of multifunctional conjugates used across chemical biology, diagnostics development, and biomaterials research.
1. Thiol-Targeted Bioconjugation
Alkyne maleimide is used to attach alkyne tags to thiol-bearing biomolecules such as peptides, proteins, and antibody fragments through maleimide-thiol coupling. Researchers rely on this reagent when they need a robust handle for subsequent click-based assembly, for example to generate defined labeling densities for mechanistic studies, binding assays, or multicomponent probe construction. The maleimide moiety provides a practical entry point for installing an alkyne functional group at specific cysteine sites, supporting workflows where orthogonal reactivity and subsequent bioorthogonal ligation are essential for building complex conjugates.
2. Fluorogenic and Imaging Probe Building
Alkyne maleimide is frequently incorporated into molecular imaging and fluorescence labeling pipelines to prepare alkyne-functional probes that can be coupled to azide-bearing reporters, affinity tags, or imaging scaffolds. In chemical biology workflows, the reagent is used to generate modular probe intermediates where the initial thiol conjugation step installs the reactive alkyne handle, and the resulting conjugates are then used for imaging reagent generation. This approach is particularly valuable when probe components must be assembled from separate building blocks to enable rapid iteration of labeling chemistry, reporter choice, and targeting moieties.
3. Surface and Material Functionalization
Alkyne maleimide is applied to functionalize biomaterial surfaces and polymer materials by introducing maleimide-reactive chemistry that captures thiol groups present on linkers, coatings, or thiolated biomolecules. Materials scientists use the reagent to create alkyne-bearing interfaces that can later be patterned or crosslinked using click-compatible partners, enabling fabrication of bioactive coatings, immobilized capture surfaces, and modular sensor architectures. The bifunctional design supports integration of biological recognition elements with downstream click-based coupling, which is commonly used to tune surface composition and enable reproducible assembly of multilayer constructs.
4. Diagnostic Reagent and Assay Linkers
Alkyne maleimide is used in the development of diagnostic and analytical reagent components where controlled conjugation of thiol-containing capture molecules is needed before installing a clickable handle for assay assembly. Assay developers often generate intermediate alkyne-functional conjugates that can be coupled to azide-bearing detection reagents, bead chemistries, or reporter constructs to build multivalent sensing formats. This reagent supports streamlined linker preparation for workflows requiring consistent attachment of functional groups to biomolecular reagents, facilitating the construction of assay-ready conjugates used in research and laboratory testing environments.
Computed Properties
| XLogP3 | -0.3 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 6 |
| Exact Mass | 234.10044231 g/mol |
| Monoisotopic Mass | 234.10044231 g/mol |
| Topological Polar Surface Area | 66.5Ų |
| Heavy Atom Count | 17 |
| Formal Charge | 0 |
| Complexity | 385 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently-Bonded Unit Count | 1 |
| Compound Is Canonicalized | Yes |
Patents
| Publication Number | Title | Priority Date |
|---|---|---|
| WO-2021260176-A1 | Synthetic epitopes of betacoronaviruses | 2020-06-25 |
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