1263291-41-3

Usage

Uses

Used in Pharmaceutical Industry:
(1α,8α,9α)-bicyclo[6.1.0]non-4-yn-9-ylmethanol is used as a building block for the synthesis of other organic compounds, particularly in the pharmaceutical industry. Its unique structure and properties make it an interesting target for research and potential uses in drug development.
Used in Organic Synthesis:
(1α,8α,9α)-bicyclo[6.1.0]non-4-yn-9-ylmethanol is used as a key intermediate in the synthesis of various organic compounds. Its specific structure allows for the formation of new chemical bonds and reactions, making it a valuable component in the creation of complex molecules for various applications.

Upstream product

• 1552-12-1 1,5-cis,cis-cyclooctadiene 
• 5259-72-3 cyclo-octa-1,5-diene 
• 1312010-01-7 C₁₀H₁₆O 
• 79549-89-6 C₁₂H₁₈O₂ 

Downstream Products

• 1493802-77-9 1-({[(1R,8S,9s)-bicyclo[6.1.0]non-4-yn-9-ylmethoxy]carbonyl}oxy)pyrrolidine-2,5-dione 
• 1380006-72-3 (1α,8α,9α)-bicyclo[6.1.0]non-4-yn-9-ylmethyl (4-nitrophenyl)carbonate 
• 201230-82-2 carbon monoxide 

Relevant academic research and scientific papers

Bio-Orthogonal T Cell Targeting Strategy for Robustly Enhancing Cytotoxicity against Tumor Cells

T cells can kill tumor cells by cell surface immunological recognition, but low affinity for tumor-associated antigens could lead to T cell off-target effects. Herein, a universal T cell targeting strategy based on bio-orthogonal chemistry and glycol-meta

A Covalent Approach for Site-Specific RNA Labeling in Mammalian Cells

Advances in RNA research and RNA nanotechnology depend on the ability to manipulate and probe RNA with high precision through chemical approaches, both in vitro and in mammalian cells. However, covalent RNA labeling methods with scope and versatility comp

Engineering Dirhodium Artificial Metalloenzymes for Diazo Coupling Cascade Reactions**

Artificial metalloenzymes (ArMs) are commonly used to control the stereoselectivity of catalytic reactions, but controlling chemoselectivity remains challenging. In this study, we engineer a dirhodium ArM to catalyze diazo cross-coupling to form an alkene that, in a one-pot cascade reaction, is reduced to an alkane with high enantioselectivity (typically >99 % ee) by an alkene reductase. The numerous protein and small molecule components required for the cascade reaction had minimal effect on ArM catalysis. Directed evolution of the ArM led to improved yields and E/Z selectivities for a variety of substrates, which translated to cascade reaction yields. MD simulations of ArM variants were used to understand the structural role of the cofactor on ArM conformational dynamics. These results highlight the ability of ArMs to control both catalyst stereoselectivity and chemoselectivity to enable reactions in complex media that would otherwise lead to undesired side reactions.

Selective strain-promoted azide-alkyne cycloadditions through transient protection of bicyclo[6.1.0]nonynes with silver or gold

Complexation of bicyclo[6.1.0]nonynes with a cationic silver or gold salt results in protection from a click reaction with azides. The cycloalkyne protection using the silver or gold salt enables selective strain-promoted azide-alkyne cycloadditions of di

Bicyclo[6.1.0]nonyne and tetrazine amino acids for Diels-Alder reactions

Here we report a general method for the de novo synthesis of a bicyclo[6.1.0]nonyne group containing an amino acid, and used Marfey's reagent for chiral analysis. This unnatural amino acid offered exceptional reactivity in the inverse electron demand Diels-Alder cycloaddition with tetrazine containing amino acids. The subsequent selective labeling of living cells at low dye concentrations demonstrated the usefulness of the new amino acid for future imaging studies. This work also laid the foundation for introducing this unnatural amino acid into peptides based on the solid-phase synthesis method.

Synthesis and evaluation of fluorescent Pam3Cys peptide conjugates

Chirally pure R- and S-epimers of TLR2 ligand Pam3CysSK4were prepared and separately conjugated to an OVA model epitope, in which lysine was replaced by azidonorleucine. The azide function in the conjugate permitted labelling with di

Solid-Phase Enrichment and Analysis of Azide-Labeled Natural Products: Fishing Downstream of Biochemical Pathways

Many methods have been devised over the decades to trace precursors of specific molecules in cellular environments as, for example, in biosynthesis studies. The advent of click chemistry has facilitated the powerful combination of tracing and at the same time sieving the highly complex metabolome for compounds derived from simple or complex starting materials, especially when the click reaction takes place on a solid support. While the principle of solid-phase click reactions has already been successfully applied for selective protein and peptide enrichment, the successful enrichment of much smaller primary and secondary metabolites, showing great structural diversity and undergoing many different biosynthetic steps, has seen only little development. For bacterial secondary metabolism, a far broader tolerance for "clickable" precursors was observed than in ribosomal proteinogenesis, thus making this method a surprisingly valuable tool for the tracking and discovery of compounds within the cellular biochemical network. The implementation of this method has led to the identification of several new compounds from the bacterial genera Photorhabdus and Xenorhabdus, clearly proving its power.

Synthesis of a toolbox of clickable rhodamine B derivatives

Abstract An efficient method for the large-scale preparation of rhodamine B clickable derivatives has been developed. Starting from inexpensive rhodamine B as the starting material it was possible to functionalize the carboxylic functionality of rhodamine B with an azide, a strained-alkyne, a substituted triphenylphosphine, a thiol, and a maleimide. Through the synthetic strategy it was possible to obtain stable and pure clickable rhodamine compounds that can be readily used not only for chemoselectively probing biomolecules, but also for materials science.

Expanding the scope of strained-alkyne chemistry: A protection-deprotection strategy via the formation of a dicobalt-hexacarbonyl complex

A protection-deprotection strategy for strained alkynes used for bioorthogonal chemistry is reported. A strained alkyne can be protected with dicobalt-octacarbonyl and we demonstrate for the first time that a strained alkyne can be re-formed and isolated

Strain-Promoted Reaction of 1,2,4-Triazines with Bicyclononynes

Strain-promoted inverse electron-demand Diels-Alder cycloaddition (SPIEDAC) reactions between 1,2,4,5-tetrazines and strained dienophiles, such as bicyclononynes, are among the fastest bioorthogonal reactions. However, the synthesis of 1,2,4,5-tetrazines is complex and can involve volatile reagents. 1,2,4-Triazines also undergo cycloaddition reactions with acyclic and unstrained dienophiles at elevated temperatures, but their reaction with strained alkynes has not been described. We postulated that 1,2,4-triazines would react with strained alkynes at low temperatures and therefore provide an alternative to the tetrazine cycloaddition reaction for use in in vitro or in vivo labelling experiments. We describe the synthesis of a 1,2,4-triazin-3-ylalanine derivative fully compatible with the fluorenylmethyloxycarbonyl (Fmoc) strategy for peptide synthesis and demonstrate its reaction with strained bicyclononynes at 37°C with rates comparable to the reaction of azides with the same substrates. The synthetic route to triazinylalanine is readily adaptable to late-stage functionalization of other probe molecules, and the 1,2,4-triazine-SPIEDAC therefore has potential as an alternative to tetrazine cycloaddition for applications in cellular and biochemical studies.