Proteome-Wide Profiling of Targets of Cysteine reactive Small Molecules by Using Ethynyl Benziodoxolone Reagents.
The utility of alkynyl benziodoxolones for chemical proteomics applications is demonstrated by identifying the proteomic targets of curcumin, a diarylheptanoid natural product that was and still is part of multiple human clinical trials as anticancer agent.
Direct alkynylation of indole and pyrrole heterocycles.
The unique properties of benziodoxolone alkynyl periodinane 1 and gold catalysts have allowed the development of a high yielding, operationally simple reaction for the introduction of silylacetylenes on a large range of indole and pyrrole heterocycles with a wide range of functional groups.
A palladium-catalyzed aminoalkynylation strategy towards bicyclic heterocycles: synthesis of (±)-trachelanthamidine.
Sweet cyclizations: The synthesis of pyrrolizidines and indolizidine has been achieved and a two-step cyclization sequence and subsequent reduction led to the natural product (±)-trachelanthamidine.
Metal-Free Oxidative Cross Coupling of Indoles with Electron-Rich (Hetero)arenes.
Introduction of a new type of C2-substituted indole benziodoxol(on)e hypervalent iodine reagents further allowed extending the scope of the reaction to NH unprotected and C3-alkylated indoles.
Indole- and Pyrrole-BX: Bench-Stable Hypervalent Iodine Reagents for Heterocycle Umpolung.
The one-step synthesis of the bench-stable hypervalent iodine reagents IndoleBX and PyrroleBX using mild Lewis acid catalyzed conditions is reported, highlighting the unique reactivity of Indole- and Pyr Role-BX.
Total synthesis and biological evaluation of jerantinine E.
The first total synthesis of the alkaloid natural product jerantinine E is based on a selective cyclization of an aminocyclopropane. Preliminary investigations show that it inhibits the…
Ethynyl benziodoxolones: functional terminators for cell-penetrating poly(disulfide)s
- P. Morelli, Xavier Martin-Benlloch, R. Tessier, J. Waser, N. Sakai, S. Matile
- Chemistry, Biology
- 17 May 2016
Beyond the introduction of enthynyl benziodoxolones as operational terminators, the compatibility of CuAAC with poly(disulfide)s and the usefulness of doubly-labeled CPDs for structural and mechanistic studies are demonstrated.
Ethynylation of Cysteine Residues: From Peptides to Proteins in Vitro and in Living Cells
Fine-tuning of the EBX reagents allowed optimization of their reactivity and physical properties for the desired application, and under optimized conditions, high cysteine selectivity was observed.
Cyclic Hypervalent Iodine Reagents for Atom-Transfer Reactions: Beyond Trifluoromethylation.
The introduction of alkynes by using ethynylbenziodoxol(on)e (EBX) reagents has been highly successful and their use to construct carbon-heteroatom and carbon-carbon bonds will be presented.
Electrophilic alkynylation: the dark side of acetylene chemistry.
In addition to the well-established nucleophilic alkynylation, the use of electrophilic alkynes can expand tremendously the scope of acetylene transfer reactions, and sulfonyl acetylenes are efficient for alkyne transfer on carbon-centered radicals.