1,433 research outputs found

    Seeing the forest for the trees: Retrieving plant secondary biochemical pathways from metabolome networks

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    Retrosynthetic design of metabolic pathways to chemicals not found in nature

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    Biology produces a universe of chemicals whose precision and complexity is the envy of chemists. Over the last 30 years, the expansive field of metabolic engineering has many successes in optimizing the overproduction of metabolites of industrial interest, including moving natural product pathways to production hosts (e.g., plants to yeast). However, there are stunningly few examples where enzymes are artificially combined to make a chemical that is not found somewhere in nature. Here, we review these efforts and discuss the challenges limiting the construction of such pathways. An analogy is made to the retrosynthesis problem solved in chemistry using algorithmic approaches, recently harnessing artificial intelligence, noting key differences in the needs of the optimization problem. When these issues are addressed, we see a future where chemistry and biology are intertwined in reaction networks that draw on the power of both to build currently unobtainable molecules across consumer, industrial, and defense applications

    Novel R3M (M = Si, Ge) substituted furan and thiophene-derived aldimines Synthesis, electrochemistry, and biological activity [Nouvelles aldimines dérivées du furanne et du thiophène substituées par R3M (M = Si, Ge) Synthèse, électrochimie et activité biologique]

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    National audienceNew furan and thiophene derivatives of aldimines o-HO-C6H4N[dbnd]CHC4H4X(R) (X = O, S; R = H, SiMe3, SiEt3, GeMe3, GeEt3) were synthesized by condensation of o-aminophenol with the substituted aldehyde precursor. Their structure, electrochemical reduction/oxidation (in CH3CN/0.1 M Bu4NPF6), frontier orbital energies, and cytotoxicity have been studied. Their electrochemical redox potentials Ep show good correlation with the corresponding orbital energies and the difference Ep ox ‚Äď Ep red corresponds well to their orbital hardness. These new compounds have a pronounced cytotoxicity toward cancer cells of human fibrosarcoma HT-1080 and mouse hepatoma MG-22A (IC50 ‚ČÖ 1‚Äď8 őľg ml‚ąí1) that can be modulated by introducing a Me3M substituent into the fifth position of the heterocycle (e.g., IC50(Me3Si)/IC50(H) ‚Č• 50). R3M-substitution reduces the orbital hardness of the aldimines studied and facilitates oxidation, promoting their oxidative metabolism. The neighboring group effect in the őĪ-Me3Si-substituted thiophene derivative favors S-oxidation, which supposedly makes its metabolic mechanism different compared to R3M-substituted furan series (or for M = Ge in the thiophene series). Interestingly, SiMe3 and GeMe3 groups in both heterocyclic series (furan and thiophene) cause opposite trends in cytotoxicity, while the silyl group increases it, the germyl group decreases it. ¬© 2019 Acad√©mie des science

    The reactions of dimethyl carbonate and its derivatives

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