33002-26-5

Upstream product

• 623-73-4 diazoacetic acid ethyl ester 
• 1066-54-2 trimethylsilylacetylene 
• 6224-91-5 trimethyl(prop-1-ynyl)silane 

Downstream Products

• 1402265-29-5 C₇H₁₁NO₂ 
• 1407593-29-6 pentafluorophenyl 2-methylcycloprop-2-enecarboxylate 
• 79671-38-8 1-methyl-2-trimethylsilyl-3-formylcyclopropene 
• 1515861-58-1 (2-methylcycloprop-2-en-1-yl)methyl (4-nitrophenyl) carbonate 
• 1407593-24-1 C₁₃H₁₃NO₅ 

Relevant academic research and scientific papers

Strain-Promoted Cycloaddition of Cyclopropenes with o-Quinones: A Rapid Click Reaction

Novel click reactions are of continued interest in fields as diverse as bio-conjugation, polymer science and surface chemistry. Qualification as a proper “click” reaction requires stringent criteria, including fast kinetics and high conversion, to be met. Herein, we report a novel strain-promoted cycloaddition between cyclopropenes and o-quinones in solution and on a surface. We demonstrate the “click character” of the reaction in solution and on surfaces for both monolayer and polymer brush functionalization.

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.

Live-cell imaging and profiling of c-Jun N-terminal kinases using covalent inhibitor-derived probes

c-Jun N-terminal kinases (JNKs) are involved in critical cellular functions. Herein, small-molecule JNK-targeting probes are reported based on a covalent inhibitor. Together with newly developed two-photon fluorescence Turn-ON reporters and chemoproteomic studies, we showed that some probes may be suitable for live-cell imaging and profiling of JNKs.

Expanding the Scope of Metabolic Glycan Labeling in Arabidopsis thaliana

Metabolic glycan labeling (MGL) has gained wide utility and has become a useful tool for probing glycosylation in living systems. For the past three decades, the development and application of MGL have mostly focused on animal glycosylation. Recently, exploiting MGL for studying plant glycosylation has gained interest. Here, we describe a systematic evaluation of MGL for fluorescence imaging of root glycans in Arabidopsis thaliana. Nineteen monosaccharide analogues containing a bioorthogonal group (azide, alkyne, or cyclopropene) were synthesized and evaluated for metabolic incorporation into root glycans. Among these unnatural sugars, 14 (including three new compounds) were evaluated in plants for the first time. Our results showed that five unnatural sugars metabolically labeled root glycans efficiently, and enabled fluorescence imaging by bioorthogonal conjugation with fluorophores. We optimized the experimental procedures for MGL in Arabidopsis. Finally, distinct distribution patterns of the newly synthesized glycans were observed along the root developmental zones, thus indicating regulated biosynthesis of glycans during root development. We envision that MGL will find broad applications in plant glycobiology.

Cyclopropenation of internal alkynylsilanes and diazoacetates catalyzed by copper(i) N-heterocyclic carbene complexes

Copper(i) N-heterocyclic carbene (CuNHC) complexes are more catalytically active than traditional transition metal salts for the cyclopropenation of internal alkynylsilanes and diazoacetate compounds. A series of 1,2,3-trisubstituted and 1,2,3,3-tetrasubstituted cyclopropenylsilane compounds were isolated in good overall yields. An interesting regioselective and chemodivergent reaction pathway was also observed to furnish a tetra-substituted furan for an electron-rich donor/acceptor diazoacetate. Finally, a practical synthesis of a cyclopropenyl-containing starting material that is useful for bioorthogonal chemistry is also described.

Ring-opening metathesis polymerization of 1,2-disubstituted cyclopropenes

The ring-opening metathesis polymerization (ROMP) of 1,2-disubstituted cyclopropenes (CPs) has been explored for the first time using Grubbs 3rd generation catalyst. A range of 1,2-CPs yielded polymers with controllable MWs and low dispersitities, and all

Functionalized cyclopropenes as bioorthogonal chemical reporters

Chemical reporters are unique functional groups that can be used to label biomolecules in living systems. Only a handful of broadly applicable reporters have been identified to date, owing to the rigorous demands placed on these functional groups in biolo

Diastereoselective intermolecular Pauson-Khand reactions of chiral cyclopropenes

(Chemical Equation Presented) In this Letter, it is demonstrated that the unusual reactivity of cyclopropenes can increase the scope and utility of intermolecular Pauson-Khand reactions. The well-defined chiral environment of cyclopropenes has a powerful

SYNTHESIS OF 3-VINYLCYCLOPROPENE DERIVATIVES

Derivatives of 3-vinylcyclopropene were synthesized from 1,2-dimethyl-3-acetyl-, 1,2-dimethyl-3-formyl-, and 1-methyl-2-trimethylsilyl-3-formylcyclopropenes and the corresponding triphenylalkylidenephosphoranes.