A5080327379- Crystallization and Solubility Studies
- X-ray Diffraction in Crystallography
- Marine Sponges and Natural Products
- Microbial Natural Products and Biosynthesis
- Synthetic Organic Chemistry Methods
- Natural product bioactivities and synthesis
- Chemical Synthesis and Analysis
- Chemical synthesis and alkaloids
- Phytochemistry and Biological Activities
- Traditional and Medicinal Uses of Annonaceae
- Carbohydrate Chemistry and Synthesis
- Cholinesterase and Neurodegenerative Diseases
- Biological Activity of Diterpenoids and Biflavonoids
- Biochemical and Molecular Research
- Plant biochemistry and biosynthesis
- Bioactive Compounds and Antitumor Agents
- Molecular spectroscopy and chirality
- Radical Photochemical Reactions
- Asymmetric Synthesis and Catalysis
- Enzyme Catalysis and Immobilization
- Photosynthetic Processes and Mechanisms
- Catalytic C–H Functionalization Methods
- Oxidative Organic Chemistry Reactions
- Fluorine in Organic Chemistry
- Plant and fungal interactions
Shanghai Jiao Tong University
2024-2025
Shanghai Advanced Research Institute
2024-2025
Institute for Advanced Study
2025
Lawrence Livermore National Laboratory
2023-2024
University of California, Los Angeles
2019-2023
University of Mississippi
2012-2022
University of Pennsylvania
2014-2019
Monell Chemical Senses Center
2015-2018
Chengdu University
2016
Philadelphia University
2015-2016
Here we report a nonenzymatic glycosylation reaction that builds axial S-glycosidic bonds under biorelevant conditions. This strategy is enabled by the design and use of allyl glycosyl sulfones as precursors to radicals exploits exceptional functional group tolerance radical processes. Our method introduces variety unprotected units cysteine residues peptides in highly selective fashion. Through developing second-generation protocol, applied our direct complex polypeptides proteins....
We report here the orchestration of molecular ion networking and a set computationally assisted structural elucidation approaches in discovery new class pyrroloiminoquinone alkaloids that possess selective bioactivity against pancreatic cancer cell lines. Aleutianamine represents first possessing highly strained multibridged ring system, discovered from Latrunculia (Latrunculia) austini Samaai, Kelly & Gibbons, 2006 (class Demospongiae, order Poecilosclerida, family Latrunculiidae) recovered...
Abstract Pyridoxal 5’‐phosphate (PLP)‐dependent enzymes that catalyze γ‐replacement reactions are prevalent, yet their utilization of carbon nucleophile substrates is rare. The recent discovery two PLP‐dependent enzymes, CndF and Fub7, has unveiled unique C−C bond forming capabilities, enabling the biocatalytic synthesis alkyl‐ substituted pipecolic acids from O‐ acetyl‐L‐homoserine β‐keto acid or aldehyde derived enolates. This breakthrough presents fresh avenues for biosynthesis...
Four new alkaloids, (−)-8′-oxo-agelasine D (2), ageloxime B (3), (+)-2-oxo-agelasidine C (4), and 4-bromo-N-(butoxymethyl)-1H-pyrrole-2-carboxamide (5), the known compound (−)-ageloxime (1) were isolated from marine sponge Agelas mauritiana. Their chemical structures established on basis of spectroscopic analysis. Compounds 1 3 both showed antifungal activity against Cryptococcus neoformans antileishmanial Leishmania donovani in vitro. Compound also exhibited antibacterial Staphylococcus...
A convergent total synthesis of the architecturally complex indole diterpenoid (−)-nodulisporic acid D has been achieved. Key synthetic transformations include vicinal difunctionalization an advanced α,β-unsaturated aldehyde to form E,F-trans-fused 5,6-ring system eastern hemisphere and a cascade cross-coupling/indolization protocol leading CDE multisubstituted core.
Nature harnesses exquisite enzymatic cascades to construct N-heterocycles and further uses these building blocks assemble the molecules of life. Here we report an platform important chiral N-heterocyclic products, pyrrolidines indolines, via abiological intramolecular C(sp3)–H amination organic azides. Directed evolution cytochrome P411 (a P450 enzyme with serine as heme-ligating residue) yielded variant P411-PYS-5149, capable catalyzing insertion alkyl nitrene into bonds build pyrrolidine...
An architecturally complex spiroketal diterpenoid, leonuketal (1), was isolated from the aerial parts of plant Leonurus japonicus. This compound possessed an unprecedented tetracyclic skeleton that comprised a bridged moiety fused with ketal-γ-lactone unit. The structure and absolute configuration were determined by spectroscopic analyses, modified Mosher's method, ECD (electronic circular dichroism) calculations. Leonuketal (1) showed significant vasorelaxant activity against KCl-induced...
Visible-light-induced generation of dithianyl and dioxolanyl radicals via selective hydrogen atom transfer (HAT) has been achieved. This radical relay tactic enables remote C(sp3)–H functionalization to permit rapid access polyol spiroketal segments, in turn exploited as a key synthetic construct the total synthesis danshenspiroketallactones. The conformational stability danshenspiroketallactones also defined experiments DFT calculations.
Monoterpene indole alkaloids are a large class of natural products derived from single biosynthetic precursor, strictosidine. We describe synthetic approach to strictosidine that relies on key facially selective Diels-Alder reaction between glucosyl-modified alkene and an enal set the C15-C20-C21 stereotriad. DFT calculations were used examine origin stereoselectivity in this step, wherein two 16 possible isomers predominantly formed. These suggest presence glucosyl unit, also inherent...
An ambimodal transition state (TS) that leads to formation of four different pericyclic reaction products ([4 + 6]-, [2 8]-, [8 2]-, and [6 4]-cycloadducts) without any intervening minima has been designed explored with DFT computations quasiclassical molecular dynamics. Direct dynamics simulations propagated from the TS show evolution trajectories give cycloadducts. The topography PES is a key factor in product selectivity. A good correlation observed between geometrical resemblance...
Lignin valorization is being intensely pursued via tandem catalytic depolymerization and biological funneling to produce single products. In many lignin processes, aromatic dimers oligomers linked by carbon-carbon bonds remain intact, necessitating the development of enzymes capable cleaving these compounds monomers. Recently, catabolism erythro-1,2-diguaiacylpropane-1,3-diol (erythro-DGPD), a ring-opened lignin-derived β-1 dimer, was reported in Novosphingobium aromaticivorans. The first...
New potential treatments for disseminated fungal infections are needed, especially caused by the commonly drug-resistant pathogens Candida albicans and C. glabrata. These cause systemic candidiasis, a significant of mortality in immune-compromised patients. ABC transporters pleiotropic drug resistance subfamily, such as Cdr1p albicans, play an important role antifungal bioassay targets therapies against pathogens. We observed strong growth inhibitory activity methanol extract Dalea formosa...
A highly convergent, stereocontrolled total synthesis of the architecturally complex marine sponge metabolite (−)-enigmazole has been achieved. Highlights include an unprecedented late-stage large-fragment Petasis–Ferrier union/rearrangement, a multicomponent Type I Anion Relay Chemistry (ARC) tactic, and dithiane–epoxide union in conjunction with oxazole-directed stereoselective reduction.
11 new (including an unprecedented skeleton, <bold>3</bold>) and 28 related known diterpenoids with interesting PTP1B inhibitory effects were identified.
Twelve new ent-abietane diterpenoids, chlorabietins A-L (), were isolated from the roots of Chloranthus oldhamii. Their structures and absolute configurations determined by extensive spectroscopic analyses, X-ray diffraction, experimental/calculated electronic circular dichroism (ECD) spectroscopy. Among isolates, D () E are first two naturally occurring 8-spiro-fused 9,10-seco-ent-abietanes containing an unexpected cis-fused A/B ring system. Chlorabietin F is a rare chinane-type diterpenoid...
We report the genome-guided discovery of sungeidines, a class microbial secondary metabolites with unique structural features. Despite evolutionary relationships dynemicin-type enediynes, sungeidines are produced by biosynthetic gene cluster (BGC) that exhibits distinct differences from known enediyne BGCs. Our studies suggest assembled two octaketide chains processed differently than those enediynes. The biosynthesis also involves activating sulfotransferase promotes dehydration reaction....
A new pyrroloiminoquinone alkaloid, named atkamine, with an unusual scaffold was discovered from a cold, deep water Alaskan sponge Latrunculia sp. collected the Aleutian Islands. Olefin metathesis utilized to determine location of double bond in hydrocarbon chain. The absolute configuration determined by using computational approaches combing ECD (electronic circular dichroism) spectroscopy.