Secondary amine selective Petasis (SASP) bioconjugation

I. Total Synthesis of Microcin SF608 and (±)-Gelsemoxonine II. Novel Reagents for Amine Selective Bioconjugation

Microcin SF608 (I) is a member of the aeruginosin serine protease inhibitors (Figure 1). This novel class of cyanobacterial non-ribosomal peptides exhibits a strong inhibitory activity against pharmaceutically relevant serine proteases such as thrombin or trypsin. The aeruginosins share a common 2-carboxy-6-hydroxyoctahydroindole (Choi) core fragment. We present a synthetic strategy towards mic...

Salt Effect Accelerates Site-Selective Cysteine Bioconjugation

Highly efficient and selective chemical reactions are desired. For small molecule chemistry, the reaction rate can be varied by changing the concentration, temperature, and solvent used. In contrast for large biomolecules, the reaction rate is difficult to modify by adjusting these variables because stringent biocompatible reaction conditions are required. Here we show that adding salts can cha...

SASP reflects senescence

Amine-Reactive Fluorene Probes: Synthesis, Optical Characterization, Bioconjugation, and Two-Photon Fluorescence Imaging

With the increasing demand for confocal and two-photon fluorescence imaging, the availability of reactive probes that possess high two-photon absorptivity, high fluorescence quantum yield, and high photostability is of paramount importance. To address the demand for better-performing probes, we prepared two-photon absorbing amine-reactive fluorenyl-based probes 2-(9,9-bis(2-(2-methoxyethoxy)eth...

Amine-boranes bearing borane-incompatible functionalities: application to selective amine protection and surface functionalization.

The first general open-flask synthesis of amine-boranes with inexpensive and readily available reagents, such as sodium borohydride, sodium bicarbonate, water, and the desired amines is described. Even amines bearing borane-reactive functionalities, such as alkene, alkyne, hydroxyl, thiol, ester, amide, nitrile, and nitro are well tolerated. Some of these novel amine-boranes represent stable mo...