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A method for synthesis of cis-4-hydroxyproline analogs is described. A cis epoxide is converted into a cis-4-hydroxyproline, while the trans epoxide is converted into a ketone or a-aminolactone in the presence of Lewis and Brønsted acids. We propose the divergent chemoselectivity is controlled by H-bonding within the cis epoxide.more » « lessFree, publicly-accessible full text available May 14, 2026
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Bicknell, Josephine; Bondarenko, Ivan; Colatrella, Alice; Cabrera-Vega, Elani J; Loya, Jesus_Daniel; Botes, Delbert S; Mellies, Jay L; Campillo-Alvarado, Gonzalo (, RSC Pharmaceutics)We describe the formation of a multidrug salt comprising sulbactam (SUL, β-lactamase inhibitor) and amantadine (AMNH, antiviral). Physicochemical investigation of the SUL·AMNH salt revealed enhanced thermal stability compared to pristine starting materials. In vitro studies found that salt formation in SUL·AMNH does not disrupt antibacterial activity against model organisms Escherichia coli and Staphylococcus epidermidis. To our knowledge, we show the first β-lactamase inhibitor-antiviral salt where both components have been approved by the U.S. Food and Drug Administration (FDA), and the first multicomponent solid containing SUL. We envisage our strategy could inspire the design of multicomponent solids for antimicrobial combination therapies.more » « lessFree, publicly-accessible full text available November 19, 2025
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Loya, Jesus_Daniel; Agarwal, Sidhaesh A; Lutz, Nicholas; Reinheimer, Eric W; Campillo-Alvarado, Gonzalo (, CrystEngComm)Fluorination of azopyridine N-donors regulates the formation of either B ← N coordination adducts or a co-crystal with phenylboronic acid catechol ester. Specifically, the formation of B ← N adducts is promoted by azopyridines with up to four fluorines, while perfluorination affords a co-crystal via phenyl–perfluoropyridyl [π⋯πF] contacts. Electrostatic potential maps showed supramolecular bonding competition outcomes to be primarily determined by modulation of electron-donating capacity and π surfaces of azopyridine N-donors using fluorination.more » « less
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Jupiter, Isabella_J; Loya, Jesus_Daniel; Lutz, Nicholas; Sittinger, Paulina_M; Reinheimer, Eric_W; Campillo-Alvarado, Gonzalo (, Crystal Growth & Design)
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