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POSTER SESSION
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 Synthesis, Structure, and Reactivity of Compounds Bearing the SF5 Group... by Yannick KraemerFluorinated functional groups are ubiquitous in medicinal chemistry, agrochemistry, and materials due to the unique properties fluorine atoms impart on their parent molecules. However, methods to install fluorine on organic molecules have traditionally required hazardous reagents, creating a bottleneck to exploring applications of emerging fluorinated motifs, such as the pentafluorosulfanyl (SF5) and related groups... |  Generation of a de novo Fe-containing oxidase by Isaac JoynerBiocatalysis is increasingly important in synthetic chemistry, as researchers exploit the exquisite selectivity and tunability of enzymes. Furthermore, advances in the scalability and ease of use of biocatalysts have made it more accessible to chemists. Concurrently, an emerging and powerful biocatalytic tool is the de novo design of proteins using computation-based methods. In principle, de novo proteins could enable the design of enzymes that accomplish any chemical transformation... |
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 Mechanistically Guided Development of the Mild, Practical Borylation of Alkyl C–H Bonds by Isaac YuThe borylation of alkyl C–H bonds provides an avenue to the diverse functionalization of organic molecules, often with complementary selectivity to that of methods based on hydrogen atom abstraction or carbene insertion. Existing catalysts for the borylation of alkyl C–H bonds typically require harsh conditions (> 100 ºC) and a large excess of the alkane substrate, to achieve high conversion. Our laboratory has discovered that the combination of 2-methylphenanthroline and iridium enables... |  Unifying Synthesis of Pupukeanane Natural Products and Progress Toward Aphidicolin by Jack CookeIsocyanoterpene natural products, such as the pupukeanane sesquiterpenes, display antimalarial bioactivity through distinct mechanisms of action to the current leading treatments—to which drug resistance has become a significant threat over the past decade. The efficient synthesis of a diverse array of isocyanoterpenes is therefore of great importance to further investigate their underexplored potential as antimalarial therapeutics. We have achieved enantiospecific formal syntheses of... |
 Chemoenzymatic Hydroaminomethylation of Olefins to Form Linear Primary Amines by Jenna ManskeAmines are valuable commodity chemicals, serving as intermediates for industrial chemicals, such as surfactants and polymers, and they are important building blocks for fine chemicals, such as agrochemicals or pharmaceuticals. One common approach for synthesizing alkyl amines is the reductive amination of carbonyl compounds often formed from hydroformylation. This transformation of olefins to amines through the addition of CO, H2, and amine is known as hydroaminomethylation.. |  Modular, Enantioselective Entry into Multi-substituted Shape-shifting Molecules by Vanessa GonzalezShape-shifting or fluxional molecules, such as bullvalene, bullvalone, and barbaralone, are well known for their ability to readily undergo non-destructive dynamic processes. These molecules can interconvert between distinct molecular shapes via facile Cope rearrangements, with each bicyclic scaffold possessing unique chemical and physiological properties. As a result, fluxional molecules have recently seen application as drug derivatives, polymers, and ligands. While various synthetic methods.. |
 Total Synthesis of (+)-Discorhabdin V by Brandon DerstineThe discorhabdin natural products are a large subset of pyrroloiminoquinone alkaloids with a myriad of biological activities. Until recently, only a few discorhadins were completed, with none featuring a bridging carbon–nitrogen bond that is found in numerous members, including discorhabdin V. Here we report the first total synthesis and full stereochemical assignment of (+)-discorhabdin V in 13 linear steps. To access the pyrroloiminoquinone we developed a convergent N-alkylation/oxidative... |  Progress Toward the Diversification of 2-Pyrones by Kristen GardnerModular synthesis of aryl amines from alkynyl 2-pyrones: A complement to Buchwald–Hartwig amination reactions. The Buchwald–Hartwig amination is a powerful transformation that has been used over the last 25 years to form aryl amines through a cross-coupling reaction of an aryl halide and an amine with the aid of a palladium catalyst. Although the Buchwald–Hartwig coupling is a powerful transformation, it requires specific aryl halide coupling partners which could limit the aryl amines... |
 Exploration of Spirocyclic Topology Through the Total Synthesis of Urceoloids A & B by Karan GoyalThe urceoloids A and B are rearranged steroid natural products bearing a unique spiro[4.4]nonatriene core. This spirocyclic core has inspired a synthetic strategy in the which the topology of two mutually perpendicular rings could be leveraged to expedite the synthesis of the target molecule. Additionally, spiro[4.4]nonenes have been shown to exhibit unique electronics, but have been underexplored in modern organic synthesis. Through a synthetic strategy focused on the spirocyclic architecture.. |  Oxidative Cleavage of Ketoximes to Ketones using Photoexcited Nitroarenes by Lucas GöttemannThe methoxime group has emerged as a versatile directing group for a variety of C–H functionalizations. Despite its importance as a powerful functional handle, conversion of methoximes to the parent ketone, which is often desired, usually requires harsh and functional group intolerant reaction conditions. Therefore, the application of methoximes and their subsequent conversion to the corresponding ketone in a late-stage context can be problematic. Here, we present an alternative set... |
 Development of a C–C Bond Cleavage/Vinylation/Mizoroki–Heck Cascade Reaction by Suh Hyun KangA C−C bond cleavage/vinylation/Mizoroki−Heck cascade reaction has been developed to provide access to densely functionalized bicyclo[2.2.2]octane frameworks. The sequence proceeds through the coupling of dihydroxylated pinene derivatives, prepared from carvone, with gem-dichloroalkenes. Using this method, 12-step total syntheses of both 14- and 15-hydroxypatchoulol have been accomplished (J. Am. Chem. Soc. 2022, 144, 19253–19257). During this work, we have identified products of... |  Desymmetrization of Heterocyclic Sulfonimidamides by Asym. Tsuji-Trost... by Garrett Toth-WilliamsMethodologies enabling the synthesis of enantioenriched sulfonimidamides containing a stereogenic sulfur center are scarce, often relying on diastereomeric crystallization or the use of chiral auxiliaries. The prototropic tautomerization exhibited by sulfonimidamides makes them uniquely suited for resolution processes. In the case where both nitrogen substituents of a disubstituted sulfonimidamide are the same, the two tautomers are also enantiomers, allowing deprotonation to generate... |
 Photo-Brook Rearr. of Acyl Silanes as a Strategy for Photoaffinity Probe Design by Annika PagePhotoaffinity labeling (PAL) is a powerful tool for the identification of non-covalent small molecule–protein interactions that are critical to drug discovery and medicinal chemistry, but this approach is limited to only a small subset of robust photocrosslinkers. The identification of new photoreactive motifs capable of covalent target capture is therefore highly desirable. We report the design, synthesis, and evaluation of a new class of PAL warheads based on the UV-triggered... |  Decarboxylative Cross Coupling of Kojic Acid by Justin SamfordGram-positive bacteria like Staphylococcus aureus are responsible for causing a variety of illnesses in humans, ranging from minor infections to pneumonia. S. aureus, particularly a methicillin resistant strain called MRSA, is the leading cause of hospital-associated infections worldwide as antibiotic resistance increases in S. aureus. As a result of this, new treatment methods are required to combat the virulence of MRSA. A novel approach being investigated is that of covalent inhibitor... |
 Upcycling PVC: Harvesting Carbon Locked in Waste Plastic by Chayo Fuentes ChangPolyvinyl chloride (PVC) is the third largest commodity synthetic polymer in production. While current recycling of ester-based and hydrocarbon polymers has been widely studied, little research has been conducted on PVC, largely because of the Cl content. Thus, this carbon-rich resource is thrown into landfills, where the Cl content contributes to toxicity. We propose a method of chemically upcycling PVC to produce commercially-valuable low molecular weight molecules. The first step is a... |  14N to 15N Isotopic Exchange of N Heteroaromatics through Skeletal Editing by Logan BartholomewThe selective modification of nitrogen heteroaromatics enables the development of new chemical tools and accelerates drug discovery. While methods that focus on expanding or contracting the skeletal structures of heteroaromatics are emerging, methods for the direct exchange of single core atoms remain limited. Previously, we reported a formal pyrimidine C2 deletion. Building upon this work, we have developed a method that accomplishes a direct 14N → 15N atom swap in a wide variety of nitrogen... |
Organic Synthesis
 Stabilization of 14-3-3 Protein-Protein Interactions with Covalent Molecular Glues by Markella KonstThe modulation of complex protein networks offers vast opportunities for chemical biology and drug discovery, especially for “hub” proteins. At the same time, the extensive interactome of “hub” proteins raises the question of selective targeting. Here, we are focusing on the hub protein 14-3-3, a highly abundant adaptor protein and aim to show that covalent small molecule stabilizers or molecular glues can be systematically developed to specifically modulate the function of the PPI of interest.. |  A Physical Organic Approach Towards New Fluorescent Probes for Biological Imaging by Jack McCannRhodamine dyes provide an invaluable way to study biological processes with both high spatial and temporal resolution, but due to its high energy excitation wavelength, it can exhibit pronounced phototoxicity. Longer wavelength probes have been found to circumvent this issue. The Dewar-Knott color rule states that introducing an electron-deficient group at the 10’ bridgehead position results in a bathochromic shift. We would like to expand on this known chemical space, exploring how... |
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 Chemoproteomics-enabled discovery of a covalent molecular glue degrader targeting NF-κB by Ellie KinTargeted protein degradation has arisen as a powerful therapeutic modality for degrading disease targets. While proteolysis-targeting chimera (PROTAC) design is more modular, the discovery of molecular glue degraders has been more challenging. Here, we have coupled the phenotypic screening of a covalent ligand library with chemoproteomic approaches to rapidly discover a covalent molecular glue degrader and decipher associated mechanisms. We have identified a cysteine-reactive covalent ligand... |  Target Protein Degradation through Recruitment of the CUL4A Complex Adaptor Protein DDB1 by Margot MTargeted protein degradation has arisen as a powerful therapeutic modality for eliminating proteins. Thus far, most heterobifunctional Proteolysis Targeting Chimeras (PROTACs) have utilized recruiters against substrate receptors of Cullin RING E3 ubiquitin ligases, such as cereblon and VHL. However, previous studies have surprisingly uncovered molecular glue degraders that exploit a CUL4A adaptor protein DDB1 to degrade neosubstrate proteins. Here, we sought to investigate whether DDB1... |
 Probing the mechanism of selective halogenation by vanadium-dependent haloperoxidases by Jackson BauVanadium-dependent haloperoxidases (VHPOs) are a unique family of enzymes that utilize a histidine-bound vanadate cofactor and hydrogen peroxide to oxidize aqueous halides to hypohalous acid. Historically, VHPOs have largely been understood to release hypohalous acid to react spontaneously with organic molecules. However, Streptomycete and gammaproteobacterial homologs have been discovered to catalyze asymmetric halogenation of meroterpenoid precursors and alkyl quinolones (AQ), respectively... |  An intronic RNA element modulates Factor VIII exon-16 splicing by Guillermo ChacaltanaThe human Factor VIII (F8) protein is essential for the blood coagulation cascade and specific F8 mutations can cause Hemophilia A (HA). Here, we investigated the impact of 97 HA-causing single-nucleotide mutations on F8 pre-mRNA splicing across 11 exons. 4/11 (~36.4%) F8 exons tested were sensitive to the presence of HA-causing mutations, especially exon-16. Intriguingly, RNA chemical probing analyses of exon-16 revealed a three-way junction structure at the 3´ end of intron 15... |
 Discovery and biosynthesis of salivabactin, a new antibiotic from oral bacteria by Di GuProbiotics are live bacteria that confer health benefits to the host upon consumption. Streptococcus salivarius, an over-the-counter oral probiotic, has bactericidal activity in vitro against several pathogens including Streptococcus pyogenes, otherwise known as group A streptococcus (GAS). GAS is an exclusive human pathogen that causes mild, superficial diseases such as pharyngitis and impetigo as well as life threatening invasive diseases such as necrotizing fasciitis and streptococca... |  Directed evolution of cyclase DsKabC with application of a high-throughput... by Melanie J & Alex TThe biocatalytic activity of an enzyme can be tuned by genetic sequence modification, enabling it to functionalize a wider range of substrates and catalyze new chemical transformations. One way to achieve this is by an iterative process called directed evolution (DE), a protein engineering technique that rapidly introduces mutations. DE allows for tuning and diversification of enzymes, making it a powerful tool for discovering new biocatalysts. DsKabC and GfKabC are red macroalgal enzymes... |
 New Fluorescent Indicators based on Triangulenium Dyes by Vicente ContrerasThe Calcium ion (Ca2+) is a vital secondary messenger and is involved in multiple physiological processes. Monitoring and quantifying Ca2+ transients in real time not only enriches our understanding of its role in these processes at the cellular level, but also contributes to the study of related disorders. Triangulenium dyes are known for their long lifetimes, good photostabilities, and tunable spectral properties. We design the Ca2+ sensors by coupling these dyes to the classic Ca2+... | ![Shedding light on dual emission: an in-depth investigation of benzo[b]... by Kayla Belavek](https://static.wixstatic.com/media/826f2e_829436faf66a450c8425c15bba72475e~mv2.jpg/v1/fill/w_250,h_134,al_c,q_90,enc_auto/826f2e_829436faf66a450c8425c15bba72475e~mv2.jpg) Shedding light on dual emission: an in-depth investigation of benzo[b]... by Kayla BelavekCalcium ion (Ca²⁺) is an important second messenger that is responsive to many physiological processes, including neurotransmitter release, muscle contraction, and fertilization. Small molecule calcium indicators are often employed to monitor Ca²⁺ dynamics. Ratio-based Ca²⁺ indicators offer the benefit of quantifying Ca²⁺ transients in complex biological environments. Fura-2 is one of the most widely used ratio-based Ca²⁺ indicators; however, its ultraviolet (UV) excitation profile truly... |
 Exploring the Role of Chemical Reactions in the Selectivity of Tyrosine Kinase... by Mojgan AsadiA variety of diseases are associated with tyrosine kinase enzymes that activate many proteins via signal transduc5on cascades. The similar ATP-binding pockets of these tyrosine kinases make it extremely difficult to design selec5ve covalent inhibitors. The present study explores the contribu5on of the chemical reac5on steps to the selec5vity of the commercialized inhibitor acalabru5nib over Bruton’s tyrosine kinase (BTK) and the interleukin-2- inducible T-cell kinase (ITK)... |  Development of a multi-scale interactome profiling platform using proximity labeling by Lindsey LinIn cancer immunology, protein interactions are pivotal to protein signaling, especially in mediating immune responses within the tumor microenvironment. These interactions take place across a wide range of length scales, making it difficult to map a given protein’s interactome with maximal coverage and resolution. Although recent advances have dramatically improved interactomics profiling, current methods using photocatalytic proximity labeling are restricted to mapping interactions... |
 Biochemical investigation of piperazinone biosynthesis in actinomycetes by Jennifer CordozaAntibiotic resistance is a looming threat that requires the search for new treatments to combat new resistant microbial strains. One such molecule is TLN-05220, a polyketide-peptide hybrid, isolated initially from Micromonospora echinospora ssp. challisensis NRRL 12255 by Thallion Pharmaceuticals in 2009. This molecule displayed antibiotic activity comparable to vancomycin, making it an intriguing candidate for further research. TLN-05220 contains a piperazinone ring found in other small... |  Rational Chemical Design of Molecular Glue Degraders by Ethan TorikiTargeted protein degradation with molecular glue degraders has arisen as a powerful therapeutic modality for eliminating classically undruggable disease-causing proteins through proteasome-mediated degradation. However, we currently lack rational chemical design principles for converting protein-targeting ligands into molecular glue degraders. To overcome this challenge, we sought to identify a transposable chemical handle that would convert protein-targeting ligands into molecular degraders... |
Chemical Biology & Bioinorganic
 Elucidating Factors of Tunneling Contributions in Thermal Electrocyclic Reactions... by Ishika JainSix-electron electrocyclic reactions usually require relatively high temperatures; however recent research has shown that such reactions can occur at significantly lower temperatures in biosynthetic and biomimetic pathways. Pathways resulting in bicyclo[4.2.0]octa-2,4-diene moieties arise from thermally allowed 8π-6π electrocyclization cascade reactions of 1,3,5,7-octatetraenes, as in the biosynthesis of endiandric acids, elysiapyrones, and numerous other natural products... |  Cleave the Way: Self-Immolative DNA Alkylators and their Selective Action by Karina BhavsarCurrent chemotherapeutic drugs that are available and used in clinical settings, while effective, are limited by their low selectivity and high toxicity. These drugs are cytotoxic molecules that cause damage in cells in order to trigger apoptosis, specifically, by reacting with DNA bases. Our goal is to synthesize a DNA alkylating chemotherapeutic prodrug that would remain active in cancer cells, but undergo an intramolecular cyclization elsewhere in the body to become inert... |
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 Rational design of molecule glue by Zhe ZhuangMolecular glues have demonstrated to be effective therapeutic agents with drug-like properties for eliminating disease-relevant proteins. These compounds leverage complementary protein–protein interfaces to facilitate cooperative interactions between ligases and target proteins. However, the underlying principles governing their discovery, design, and optimization have remained poorly understood. During my postdoctoral research, I have developed a rational approach to designing... |  Development and Mechanistic Analysis of Covalent Inhibitors Against Sortase A... by Clifford LeungTraditional antibiotics are either bactericidal or bacteriostatic, resulting in evolutionary pressure on bacteria to develop resistance. Recent studies have shown that targeting the bacteria’s pathogenicity, rather than its vital nuclear functions, may present a promising alternative. Sortase A (SrtA), a cysteine protease found in Staphylococcus aureus (S. aureus) and other gram-positive bacteria, promotes virulence by catalyzing the transpeptidation of pilin-like structures... |
 Leveraging Chromatographic Lipophilicity to Predict the Passive Cell Permeability... by Grant KochEncoded libraries of peptide macrocycles have seen a surge of recent success at delivering potent compounds to the clinic whose targets are validated, highly sought after protein-protein interactions. The massive encoding power of DNA-encoded libraries and mRNA display libraries yields unparalleled discovery power against challenging targets but tends to select and concentrate compounds with relatively more polar functionalities. This natural proclivity to select highly polar compounds... |  Multicomponent Reaction Approach to Discovery of Selective CRBN-based Molecular... by Hlib Razumkov |
 In silico characterization of potential serum response factor inhibitors in... by Clinton CunhaSerum response factor is a transcription factor present in all types of cells and plays a role in muscle tissue development. SRF is activated by growth factor stimulation and mitosis, leading to the expression of genes that influence growth and the cytoskeleton. Additionally, SRF in gastric cancer is associated with an aggressive phenotype and a poor outcome due to the downregulation of E-cadherin which promotes the epithelial-mesenchymal transition. Furthermore, in colorectal cancer, SRF... |
Medicinal & Computational Chemistry
 EWOC NorCal ChapterCome learn about the NorCal chapter of Empowering Women in Chemistry (EWOC)! We work toward a future in science where equal opportunity is available to people of all genders and the our meeting is no longer required. We are ramping up our events in the coming year - networking, research symposia, workshops, mentoring programs, and more. Allies are always welcome! |
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