1263166-90-0

Usage

Uses

Used in Bioconjugation Applications:
(1R,8S,9S)‐bicyclo[6.1.0]non‐4‐yn‐9‐ylmethanol is used as a bioconjugation agent for the efficient and site-specific labeling of biomolecules. Its unique strained cyclooctyne structure allows it to react with azide functionalized compounds or biomolecules without the need for a copper catalyst, resulting in a stable triazole linkage.
Used in Drug Delivery Systems:
(1R,8S,9S)‐bicyclo[6.1.0]non‐4‐yn‐9‐ylmethanol is used as a drug delivery carrier for targeted and controlled release of therapeutic agents. Its ability to form stable triazole linkages with azide functionalized drug molecules enables the development of novel drug delivery systems with improved bioavailability and therapeutic outcomes.
Used in Chemical Synthesis:
(1R,8S,9S)‐bicyclo[6.1.0]non‐4‐yn‐9‐ylmethanol is used as a synthetic building block for the preparation of various organic compounds and materials. Its unique structure and reactivity make it a valuable component in the synthesis of complex organic molecules and advanced materials with potential applications in various industries.

Upstream product

• 1552-12-1 1,5-cis,cis-cyclooctadiene 
• 374898-56-3 C₁₀H₁₆O 
• 1263291-39-9 C₁₂H₁₈O₂ 
• 5259-72-3 cyclo-octa-1,5-diene 

Downstream Products

• 1285573-35-4 ((5aS,6S,6aR)-3-(4-methoxyphenyl)-5,5a,6,6a,7,8-hexahydro-4H-cyclopropa[5,6]cycloocta[1,2-d]isoxazol-6-yl)methanol 
• 1285573-43-4 ((5aS,6S,6aR)-3-(perfluorophenyl)-5,5a,6,6a,7,8-hexahydro-4H-cyclopropa[5,6]cycloocta[1,2-d]isoxazol-6-yl)methanol 
• 1285573-46-7 ((5aS,6S,6aR)-3-((E)-styryl)-5,5a,6,6a,7,8-hexahydro-4H-cyclopropa[5,6]cycloocta[1,2-d]isoxazol-6-yl)methanol 
• 1285573-31-0 ((5aS,6S,6aR)-3-phenyl-5,5a,6,6a,7,8-hexahydro-4H-cyclopropa[5,6]cycloocta[1,2-d]isoxazol-6-yl)methanol 
• 1285573-39-8 ((5aS,6S,6aR)-3-(4-nitrophenyl)-5,5a,6,6a,7,8-hexahydro-4H-cyclopropa[5,6]cycloocta[1,2-d]isoxazol-6-yl)methanol 
• 1355176-96-3 C₂₄H₂₄N₂O 

Relevant academic research and scientific papers

Synthesis of BODIPY-Labeled Cholesterylated Glycopeptides by Tandem Click Chemistry for Glycocalyxification of Giant Unilamellar Vesicles (GUVs)

The glycocalyx cover membrane surfaces of all living cells. These complex architectures render their interaction mechanisms on the membrane surface difficult to study. Artificial cell-sized membranes with selected and defined glycosylation patterns may serve as a minimalistic approach to systematically study cell surface glycan interactions. The development of a facile general synthetic procedure for the synthesis of BODIPY-labeled cholesterylated glycopeptides, which can coat cell-size giant unilamellar vesicles (GUVs), is described. These peptide constructs were synthesized by: 1) solid-phase peptide synthesis (SPPS) using cholesterylated Fmoc-amino acids (Fmoc=9-fluorenylmethoxycarbonyl) followed by tandem click reactions, 2) attachment of a BODIPY-bicyclononyne (BCN) (prepared by Mitsunobu chemistry via novel aryl BCN-ethers) in the absence of a catalyst, and 3) glycosylation by means of copper(I)-catalyzed click reaction of an azidoglycan. Seven different GUV-glycoforms were prepared and four of these were evaluated with their corresponding four specific anti-glycan binding lectins.

Readily accessible bicyclononynes for bioorthogonal labeling and three-dimensional imaging of living cells

I can see clearly now: Bicyclo[6.1.0]non-4-yne, an easily prepared, symmetrical cycloalkyne, displays excellent reaction kinetics in strain-promoted cycloaddition reactions with azides and nitrones (see scheme). Highly specific protein modifications are d

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.

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

Bicyclo[6.1.0]nonyne carboxylic acid for the production of stable molecular probes

Bicyclo[6.1.0]non-4-yn-9-ylmethanol (BCN alcohol) is the most prominent strained-alkyne scaffold in chemical biology. Described herein is the synthesis of an oxidized analogue-BCN acid-whose facile functionalization via amide bond formation yields more st

Chemical Targeting of Voltage Sensitive Dyes to Specific Cells and Molecules in the Brain

Voltage sensitive fluorescent dyes (VSDs) are important tools for probing signal transduction in neurons and other excitable cells. The impact of these highly lipophilic sensors has, however, been limited due to the lack of cell-specific targeting methods in brain tissue or living animals. We address this key challenge by introducing a nongenetic molecular platform for cell- and molecule-specific targeting of synthetic VSDs in the brain. We employ a dextran polymer particle to overcome the inherent lipophilicity of VSDs by dynamic encapsulation and high-affinity ligands to target the construct to specific neuronal cells utilizing only native components of the neurotransmission machinery at physiological expression levels. Dichloropane, a monoamine transporter ligand, enables targeting of dense dopaminergic axons in the mouse striatum and sparse noradrenergic axons in the mouse cortex in acute brain slices. PFQX in conjunction with ligand-directed acyl imidazole chemistry enables covalent labeling of AMPA-type glutamate receptors in the same brain regions. Probe variants bearing either a classical electrochromic ANEP dye or state-of-the-art VoltageFluor-type dye respond to membrane potential changes in a similar manner to the parent dyes, as shown by whole-cell patch recording. We demonstrate the feasibility of optical voltage recording with our probes in brain tissue with one-photon and two-photon fluorescence microscopy and define the signal limits of optical voltage imaging with synthetic sensors under a low photon budget determined by the native expression levels of the target proteins. This work demonstrates the feasibility of a chemical targeting approach and expands the possibilities of cell-specific imaging and pharmacology.

A Bioorthogonal Click Chemistry Toolbox for Targeted Synthesis of Branched and Well-Defined Protein–Protein Conjugates

Bioorthogonal chemistry holds great potential to generate difficult-to-access protein–protein conjugate architectures. Current applications are hampered by challenging protein expression systems, slow conjugation chemistry, use of undesirable catalysts, or often do not result in quantitative product formation. Here we present a highly efficient technology for protein functionalization with commonly used bioorthogonal motifs for Diels–Alder cycloaddition with inverse electron demand (DAinv). With the aim of precisely generating branched protein chimeras, we systematically assessed the reactivity, stability and side product formation of various bioorthogonal chemistries directly at the protein level. We demonstrate the efficiency and versatility of our conjugation platform using different functional proteins and the therapeutic antibody trastuzumab. This technology enables fast and routine access to tailored and hitherto inaccessible protein chimeras useful for a variety of scientific disciplines. We expect our work to substantially enhance antibody applications such as immunodetection and protein toxin-based targeted cancer therapies.

MOLECULAR LOGIC GATES FOR CONTROLLED MATERIAL DEGRADATION

The present disclosure features, inter alia, a cyclic multifunctional linker, including at least two cleavable moieties; at least two connecting chains connected to the at least two cleavable moieties to provide a cyclic structure; and at least two linkin

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.

Clicking 1,2,4,5-tetrazine and cyclooctynes with tunable reaction rates

Substituted tetrazines have been found to undergo facile inverse electron demand Diels-Alder reactions with "tunable" reaction rates.