Oxidative damage to DNA has been implicated in carcinogenesis during chronic inflammation. Epidemiological and biochemical studies suggest that one potential mechanism involves myeloperoxidase, a hemeprotein secreted by human phagocytes. In this study, we demonstrate that human neutrophils use myeloperoxidase to oxidize uracil to 5-chlorouracil in vitro. Uracil chlorination by myeloperoxidase o...

A green, high rate, yielding, and selective Appel reaction that make use of 1,3-dihalo-5,5-dimethylhydantoins N -halo-succinimides as halogenation reagents. The new method was developed for batch continuous flow reactors.

Halogenation matters! The stacking between phenylalanine side chains can be tuned by halogen atoms attached to the aromatic ring. Herein, computational data are successfully applied in design of peptide hydrogels with increased stiffness.

A three-center halogen bond modulates the reactivity of a halonium ion and is thereby applicable for controlling halogenation alkenes. Chelation, strain, steric hindrance, electrostatic interactions influence release rate. Combined experimental theoretical analysis reaction mechanism highlights impact secondary interactions, expected to provide handle on induction stereoselectivity in electroph...

The endogenous mu-opioid receptor agonist, endomorphin (EM)-1, cannot be delivered into the central nervous system (CNS) in sufficient quantity to elicit analgesia when given systemically because it is severely restricted by the blood-brain barrier (BBB). To improve the physicochemical characteristics of EM-1 and subsequently achieve greater BBB permeation, we synthesized a series of EM-1 analo...

Abstract Flavin‐dependent halogenases (FDHs) natively catalyze selective halogenation of electron rich aromatic and enolate groups. Nearly all FDHs reported to date require a separate flavin reductase supply them with FADH 2 , which complicates biocatalysis applications. In this study, we establish that the single component reductase/flavin dependent halogenase AetF catalyzes diverse set substr...

A range of dehydro amino acid derivatives has been prepared and subjected to halogenation using either molecular bromine or chlorine, or NBS. Allylic halogenation of the unsaturated amino acid side chains occurs through radical bromination with NBS. The procedure is complementary to treatment with chlorine, which also affords allyl halides. This latter and unusual reaction is shown through a de...