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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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Shingwekar, Deepika; Lutz, Nicholas; Botes, Delbert S; Cabrera-Vega, Elani J; Campillo-Alvarado, Gonzalo; Mellies, Jay L; Loya, Jesus Daniel (, RSC Mechanochemistry)Here, we optimized a chemo-microbial degradation of polyethylene terephthalate. Developed a path to mechanochemically interconvert between BHET polymorphs and established that BHET polymorphism influences bacterial biodegradation rate.more » « lessFree, publicly-accessible full text available November 5, 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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