N-(2-Butyn-1-yl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]glycine integrates a terminal alkyne with an Fmoc-protected backbone, enabling bioorthogonal reactivity. The residue aids in click-chemistry conjugation and distance-controlled labeling. Researchers employ it to study sterically constrained geometries and backbone flexibility. Its design suits modular synthetic strategies.
CAT No: R2180
CAS No:2639419-13-7
Synonyms/Alias:N-(2-Butyn-1-yl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]glycine;2639419-13-7;N-(2-Butyn-1-yl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]glycine;EN300-28228642;2-[(but-2-yn-1-yl)({[(9H-fluoren-9-yl)methoxy]carbonyl})amino]acetic acid;
N-(2-Butyn-1-yl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]glycine is a specialized amino acid derivative featuring both a fluorenylmethyloxycarbonyl (Fmoc) protecting group and a terminal alkyne functionality. This compound is highly valued in modern synthetic chemistry due to its dual reactivity and compatibility with solid-phase peptide synthesis (SPPS) protocols. Its unique structure enables orthogonal strategies for peptide modification, allowing for precise control over molecular assembly and functionalization. Researchers appreciate the versatility of this compound, as it seamlessly integrates into established peptide synthesis workflows while providing additional handles for post-synthetic transformations. The presence of the Fmoc group ensures stability during the initial stages of synthesis, while the 2-butyn-1-yl moiety unlocks further chemical diversification through click chemistry and other coupling methodologies.
Peptide Synthesis: In peptide chemistry, N-(2-Butyn-1-yl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]glycine serves as a valuable building block for the incorporation of alkyne-functionalized residues into peptide chains. The Fmoc group provides temporary protection for the amine, facilitating stepwise elongation on solid supports. After selective deprotection, the alkyne moiety remains available for subsequent conjugation, allowing researchers to introduce site-specific modifications or labels into the peptide backbone. This approach is particularly useful for generating peptides with unique biophysical properties or for creating tools for molecular recognition studies.
Bioorthogonal Conjugation: The terminal alkyne group in this compound is ideally suited for copper-catalyzed azide-alkyne cycloaddition (CuAAC), commonly known as click chemistry. By incorporating the alkyne-functionalized glycine into biomolecules, scientists can achieve highly selective and efficient conjugation with azide-containing partners. This strategy enables the attachment of probes, fluorophores, or affinity tags to peptides and proteins without interfering with native biological functions. As a result, it has found widespread use in the development of bioorthogonal labeling techniques for imaging, tracking, and isolating target biomolecules in complex biological environments.
Material Science: The unique reactivity of N-(2-Butyn-1-yl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]glycine extends to the field of materials science, where it is used to engineer functionalized polymers and hydrogels. By leveraging the alkyne functionality, researchers can introduce cross-linking sites or reactive handles into polymeric networks, enabling the creation of materials with tunable mechanical, chemical, or biological properties. These advanced materials are of interest for applications such as biosensing, drug delivery, and tissue engineering, where precise control over molecular architecture is essential for performance.
Chemical Biology: In chemical biology, the compound enables the generation of peptide-based probes and molecular tools for studying protein interactions, enzyme activity, and cellular processes. The orthogonal protection and functionalization strategies afforded by the Fmoc and alkyne groups allow for the incorporation of reporter molecules or reactive groups at defined positions within peptides. This precise modification capability is instrumental in elucidating structure-activity relationships and in the design of targeted molecular probes for advanced biochemical investigations.
Surface Immobilization: The alkyne functionality of this glycine derivative also facilitates the immobilization of peptides and other biomolecules onto solid surfaces via click chemistry. This application is particularly valuable in the fabrication of biosensors, microarrays, and diagnostic platforms, where stable and oriented attachment of functional molecules is required. By enabling robust covalent linkage to azide-modified surfaces, the compound supports the development of highly sensitive analytical devices and high-throughput screening technologies.
N-(2-Butyn-1-yl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]glycine continues to drive innovation across multiple scientific disciplines by providing a versatile platform for peptide modification, conjugation, and surface functionalization. Its dual protection and reactivity profile streamline the synthesis of complex biomolecules and advanced materials, empowering researchers to explore new frontiers in chemical biology, materials science, and analytical technology.
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