A5076109982- X-ray Diffraction in Crystallography
- Crystallization and Solubility Studies
- Microbial Natural Products and Biosynthesis
- Cyclopropane Reaction Mechanisms
- Plant biochemistry and biosynthesis
- Catalytic Alkyne Reactions
- Catalytic C–H Functionalization Methods
- Oxidative Organic Chemistry Reactions
- Chemical Synthesis and Analysis
- Organic Chemistry Cycloaddition Reactions
- Renin-Angiotensin System Studies
- Synthesis and pharmacology of benzodiazepine derivatives
- Radical Photochemical Reactions
- Crystallography and molecular interactions
- Fungal Biology and Applications
- Sulfur Compounds in Biology
- melanin and skin pigmentation
- Asymmetric Synthesis and Catalysis
- Photochromic and Fluorescence Chemistry
- Enzyme Catalysis and Immobilization
- Antimicrobial Peptides and Activities
- Peptidase Inhibition and Analysis
- Mast cells and histamine
- Biochemical and Molecular Research
- Natural product bioactivities and synthesis
University of California, Davis
2020-2024
Fungal meroterpenoids are a diverse group of hybrid natural products with impressive structural complexity and high potential as drug candidates. In this work, we evaluate the promiscuity early structure diversity-generating step in fungal meroterpenoid biosynthetic pathways: multibond-forming polyene cyclizations catalyzed by yet poorly understood family cyclases. total, 12 unnatural were accessed chemoenzymatically using synthetic substrates. Their complex structures determined 2D NMR...
We have developed catalyst-controlled regiodivergent rearrangements of onium-ylides derived from indole substrates. Oxonium ylides formed in situ substituted indoles selectively undergo [2,3]- and [1,2]-rearrangements the presence a rhodium copper catalyst, respectively. The combined experimental density functional theory (DFT) computational studies indicate divergent mechanistic pathways involving metal-free ylide catalyzed reaction favoring [2,3]-rearrangement, metal-coordinated ion-pair...
Abstract Fungal meroterpenoids are a diverse group of hybrid natural products with impressive structural complexity and high potential as drug candidates. In this work, we evaluate the promiscuity early structure diversity‐generating step in fungal meroterpenoid biosynthetic pathways: multibond‐forming polyene cyclizations catalyzed by yet poorly understood family cyclases. total, 12 unnatural were accessed chemoenzymatically using synthetic substrates. Their complex structures determined 2D...
Noncovalent interactions involving sulfur atoms play essential roles in protein structure and function by significantly contributing to stability, folding, biological activity. Sulfur is a highly polarizable atom that can participate many types of noncovalent including hydrogen bonding, sulfur-π interactions, S-lone pair but the impact these sulfur-based on molecular recognition drug design still often underappreciated. Here, we examine, using quantum chemical calculations, complex naturally...
We have developed catalyst-controlled regiodivergent rearrangements of onium-ylides derived from indole substrates. Oxonium ylides formed <i>in situ</i> substituted indoles selectively undergo [2,3]- and [1,2]-rearrangements in the presence a rhodium copper catalyst, respectively. The combined experimental density functional theory (DFT) computational studies indicate divergent mechanistic pathways involving metal-free ylide catalyzed reaction favoring [2,3]-rearrangement,...
Eunicellane diterpenoids are a unique family of natural products containing foundational 6/10-bicyclic framework and can be divided into two main classes, cis trans , based on the configurations their ring fusion at C1 C10. Previous studies bacterial diterpene synthases, Bnd4 AlbS, revealed that these enzymes form - -eunicellane skeletons, respectively. Although structures diterpenes only differed in configuration single position, C1, they displayed distinct chemical thermal reactivities....
Enantioselective Giese reactions employing chiral α,β-unsaturated acylammonium salts and subsequent diastereoselective trapping followed by lactamization deliver optically active δ-lactams. Alkyl iodides bearing tosylamides undergo radical initiation using triethylborane at low temperatures to provide carbon-centered radicals initiate the described organocascade. Subsequent inter- or intramolecular of incipient α-radical leads highly functionalized, enantioenriched mono- bicyclic δ-lactams...
Terpenoids are the largest family of natural products, but prokaryotes vastly underrepresented in this chemical space. However, genomics supports vast untapped biosynthetic potential for terpenoids bacteria. We discovered first trans-eunicellane terpene synthase (TS), AlbS from Streptomyces albireticuli NRRL B-1670, nature. Mutagenesis, deuterium labeling studies, and quantum calculations provided extensive support its cyclization mechanism. In addition, parallel stereospecific studies with...
We have developed catalyst-controlled regiodivergent rearrangements of onium-ylides derived from indole substrates. Oxonium ylides formed in situ substituted indoles selectively undergo [2,3]- and [1,2]-rearrangements the presence a rhodium copper catalyst, respectively. The combined experimental density functional theory (DFT) computational studies indicate divergent mechanistic pathways involving metal-free ylide catalyzed reaction favoring [2,3]-rearrangement, metal-coordinated ion-pair...