Tags: Organic Seminar


Post-Transition State Bifurcations are Gaining Momentum - Implications for Synthesis and Biosynthesis

When the steepest descent pathway following a transition state structure for a given reaction splits in two, the reaction is said to involve a post-transition state bifurcation (PTSB). The presence of a PTSB presents complications for predicting product selectivity, in that a single transition state structure allows direct access to two products without any intervening minima (intermediates). Examples of reactions from organic synthesis and…


Reactivity-Based Chemical Tools for Biomedical Research

Selective reactions with proteins carrying unique chemical reporters in living cells offer a powerful tool to study protein dynamics in their native environment. In this talk, I will discuss our work on the development of tetrazole and strained alkene reagents that allow rapid and site-specific protein labeling both in vitro and in living cells. Our optimization efforts have resulted in the tetrazole reagents with tunable photoactivation…


Supramolecular Approaches to Advanced Functional Materials

In the "bottom-up" approach, materials and devices are constructed from molecules capable of assembling themselves by principles/methods of molecular recognition. Although well-defined assemblies can be engineered by exploiting various noncovalent interactions, there are limited methods in the literature regarding the design and analysis of self-guiding molecules for materials application in which there is a strategic integrations of the self-…


Targeting kinases with constrained peptide scaffolds

Misregulation of kinases is implicated in a myriad of diseases and significant efforts have been put forth towards the development of targeted kinase inhibitors.  However, many issues remain with current therapeutic strategies including specificity and inhibitor resistance.  As an alternative approach for targeted inhibition, we have developed inhibitors targeting protein-protein interfaces (PPIs) that bind evolutionarily conserved…


Mechanistic Dichotomy in Proton-Coupled Electron Transfer Reactions of Metal-Oxygen Species


The Original Cope Rearrangement: Fundamental Studies and Applications in Complex Molecule Synthesis


Computer-Aided Synthesis Planning

  Abstract: Retrosynthetic analysis and the development of a synthetic plan is a key step in the synthesis of natural and most pharmaceutically relevant targets. The algorithmic nature of this process makes it appear amenable to automation, and in fact the development of a synthesis planning computer program was first proposed by E. J. Corey in 1967, in the same paper in which he first formalized the principles of retrosynthetic analysis.…


Self-immolative colorimetric, fluorescent and chemiluminescent chemosensors

Self-immolative chemistry has undergone rapid development in the past decades and led to molecular systems that possesses stimuli-responsive releasing properties. The unique self-immolative spacers serve as the fundamental component at these systems. They covalently link reagent-responsive group and a reporter moiety and can structurally “sacrifice” themselves in order to implement their designated function. The first self-immolative spacer was…


Human Milk Oligosaccharides: Defense Against Pathogens

As bacteria play essential roles in maintaining human health and contributing to human illness, the establishment and maintenance of a symbiotic microbiome is key to metabolic, immunologic, and hormonal homeostasis. At no time is this more important than during infancy which is a critical period of growth and immune system development. Human milk contributes substantially to the establishment of a healthy gut microbiome in breastfed infants by…


Indole Alkaloids and Phenazine Antibiotics: New Platforms for Discovery

Various natural products, such as taxol, morphine and vancomycin, play a prominent role in medicine due to their ability to modulate biological targets critical to human disease. Our lab has two natural product inspired synthetic medicinal chemistry programs, driven by the structural complexity of indole alkaloids and the function of phenazine antibiotics. Each program aims to address major biomedical problems, including: (1) enhancing…
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