Modification of N-terminal α-amine of proteins via biomimetic ortho-quinone-mediated oxidation

N-terminal protein modification through a biomimetic transamination reaction.

N-Terminal Modification of Proteins with o-Aminophenols

The synthetic modification of proteins plays an important role in chemical biology and biomaterials science. These fields provide a constant need for chemical tools that can introduce new functionality in specific locations on protein surfaces. In this work, an oxidative strategy is demonstrated for the efficient modification of N-terminal residues on peptides and N-terminal proline residues on...

Efficient generation of ortho-quinone methide: application to the biomimetic syntheses of (±)-schefflone and tocopherol trimers.

An efficient method using silver oxide-mediated oxidation for the synthesis of ortho-quinone methides has been developed and applied to the biomimetic syntheses of novel trimeric natural products, (±)-schefflone and tocopherol trimers. Further studies of the critical trimerization as well as substrate scope and limitations are also reported.

Mannich base-connected syntheses mediated by ortho-quinone methides

This article provides an overview about specifically modified Mannich reactions where the process involves an ortho-quinone methide (o-QM) intermediate. The reactions are classified on the basis of the o-QM source followed by the reactant, e.g., the dienophile partner in cycloaddition reactions (C=C or C=N dienophiles) or by the formation of multicomponent Mannich adducts. Due to the important ...

The Domestication of ortho-Quinone Methides

CONSPECTUS: An ortho-quinone methide (o-QM) is a highly reactive chemical motif harnessed by nature for a variety of purposes. Given its extraordinary reactivity and biological importance, it is surprising how few applications within organic synthesis exist. We speculate that their widespread use has been slowed by the complications that surround the preparation of their precursors, the harsh g...