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1. Chiral Single‐Molecule Potentiometers Based on Stapled ortho‐ Oligo(phenylene)ethynylenes

Author

Ortuño, Ana M., primary, Reiné, Pablo, additional, Álvarez de Cienfuegos, Luis, additional, Márquez, Irene R., additional, Dednam, Wynand, additional, Lombardi, Enrico B., additional, Palacios, Juan J., additional, Leary, Edmund, additional, Longhi, Giovanna, additional, Mujica, Vladimiro, additional, Millán, Alba, additional, González, M. Teresa, additional, Zotti, Linda A., additional, Miguel, Delia, additional, and Cuerva, Juan M., additional

Published
2023
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2. Cell Survival Enabled by Leakage of a Labile Metabolic Intermediate

Author

Medina-Carmona, Encarnación, primary, Gutierrez-Rus, Luis I, additional, Manssour-Triedo, Fadia, additional, Newton, Matilda S, additional, Gamiz-Arco, Gloria, additional, Mota, Antonio J, additional, Reiné, Pablo, additional, Cuerva, Juan Manuel, additional, Ortega-Muñoz, Mariano, additional, Andrés-León, Eduardo, additional, Ortega-Roldan, Jose Luis, additional, Seelig, Burckhard, additional, Ibarra-Molero, Beatriz, additional, and Sanchez-Ruiz, Jose M, additional

Published
2023
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3. Cell Survival Enabled by Leakage of a Labile Metabolic Intermediate

Author

Medina-Carmona, Encarnacion, Gutierrez-Rus, Luis I, Manssour-Triedo, Fadia, Newton, Matilda S, Gamiz-Arco, Gloria, Mota, Antonio J, Reiné, Pablo, Cuerva, Juan Manuel, Ortega-Muñoz, Mariano, Andrés-León, Eduardo, Ortega-Roldan, Jose Luis, Seelig, Burckhard, Ibarra-Molero, Beatriz, Sanchez-Ruiz, Jose M, Medina-Carmona, Encarnacion, Gutierrez-Rus, Luis I, Manssour-Triedo, Fadia, Newton, Matilda S, Gamiz-Arco, Gloria, Mota, Antonio J, Reiné, Pablo, Cuerva, Juan Manuel, Ortega-Muñoz, Mariano, Andrés-León, Eduardo, Ortega-Roldan, Jose Luis, Seelig, Burckhard, Ibarra-Molero, Beatriz, and Sanchez-Ruiz, Jose M

Abstract

Many metabolites are generated in one step of a biochemical pathway and consumed in a subsequent step. Such metabolic intermediates are often reactive molecules which, if allowed to freely diffuse in the intracellular milieu, could lead to undesirable side reactions and even become toxic to the cell. Therefore, metabolic intermediates are often protected as protein-bound species and directly transferred between enzyme active sites in multi-functional enzymes, multi-enzyme complexes and metabolons. Sequestration of reactive metabolic intermediates thus contributes to metabolic efficiency. It is not known, however, whether this evolutionary adaptation can be relaxed in response to challenges to organismal survival. Here, we report evolutionary repair experiments on E. coli cells in which an enzyme crucial for the biosynthesis of proline has been deleted. The deletion makes cells unable to grow in a culture medium lacking proline. Remarkably, however, cell growth is efficiently restored by many single mutations (12 at least) in the gene of glutamine synthetase. The mutations cause the leakage to the intracellular milieu of a highly reactive phosphorylated intermediate common to the biosynthetic pathways of glutamine and proline. This intermediate is generally assumed to exist only as a protein-bound species. Nevertheless, its diffusion upon mutation-induced leakage enables a new route to proline biosynthesis. Our results support that leakage of sequestered metabolic intermediates can readily occur and contribute to organismal adaptation in some scenarios. Enhanced availability of reactive molecules may enable the generation of new biochemical pathways and the potential of mutation-induced leakage in metabolic engineering is noted.

Published
2023

4. Cell Survival Enabled by Leakage of a Labile Metabolic Intermediate

Author

Human Frontier Science Program, Ministerio de Ciencia e Innovación (España), European Commission, National Aeronautics and Space Administration (US), Junta de Andalucía, Medina-Carmona, E., Gutierrez-Rus, Luis I., Manssour-Triedo, Fadia, Newton, Matilda S., Gamiz-Arco, Gloria, Mota, A. J., Reiné, Pablo, Cuerva, Juan Manuel, Ortega-Muñoz, Mariano, Andrés-León, Eduardo, Ortega-Roldan, Jose Luis, Seelig, Burckhard, Ibarra-Molero, Beatriz, Sánchez-Ruiz, J.M., Human Frontier Science Program, Ministerio de Ciencia e Innovación (España), European Commission, National Aeronautics and Space Administration (US), Junta de Andalucía, Medina-Carmona, E., Gutierrez-Rus, Luis I., Manssour-Triedo, Fadia, Newton, Matilda S., Gamiz-Arco, Gloria, Mota, A. J., Reiné, Pablo, Cuerva, Juan Manuel, Ortega-Muñoz, Mariano, Andrés-León, Eduardo, Ortega-Roldan, Jose Luis, Seelig, Burckhard, Ibarra-Molero, Beatriz, and Sánchez-Ruiz, J.M.

Abstract

Many metabolites are generated in one step of a biochemical pathway and consumed in a subsequent step. Such metabolic intermediates are often reactive molecules which, if allowed to freely diffuse in the intracellular milieu, could lead to undesirable side reactions and even become toxic to the cell. Therefore, metabolic intermediates are often protected as protein-bound species and directly transferred between enzyme active sites in multi-functional enzymes, multi-enzyme complexes, and metabolons. Sequestration of reactive metabolic intermediates thus contributes to metabolic efficiency. It is not known, however, whether this evolutionary adaptation can be relaxed in response to challenges to organismal survival. Here, we report evolutionary repair experiments on Escherichia coli cells in which an enzyme crucial for the biosynthesis of proline has been deleted. The deletion makes cells unable to grow in a culture medium lacking proline. Remarkably, however, cell growth is efficiently restored by many single mutations (12 at least) in the gene of glutamine synthetase. The mutations cause the leakage to the intracellular milieu of a highly reactive phosphorylated intermediate common to the biosynthetic pathways of glutamine and proline. This intermediate is generally assumed to exist only as a protein-bound species. Nevertheless, its diffusion upon mutation-induced leakage enables a new route to proline biosynthesis. Our results support that leakage of sequestered metabolic intermediates can readily occur and contribute to organismal adaptation in some scenarios. Enhanced availability of reactive molecules may enable the generation of new biochemical pathways and the potential of mutation-induced leakage in metabolic engineering is noted.

Published
2023

5. 2D self-assembly of o-OPE foldamers for chiroptical barcoding

Author

López-Sicilia, Irene, primary, Ortuño, Ana, additional, Reiné, Pablo, additional, Otero, Dario, additional, Martin-Romero, Maria Teresa, additional, Camacho, Luis, additional, Alvarez de Cienfuegos, Luis, additional, Orte, Angel, additional, Giner-Casares, Juan J, additional, Miguel, Delia, additional, and Cuerva, Juan Manuel, additional

Published
2023
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6. Cell survival enabled by leakage of a labile metabolic intermediate

Author

Medina-Carmona, Encarnación, primary, Gutierrez-Rus, Luis I., additional, Manssour-Triedo, Fadia, additional, Newton, Matilda S., additional, Gamiz-Arco, Gloria, additional, Mota, Antonio J., additional, Reiné, Pablo, additional, Cuerva, Juan Manuel, additional, Ortega-Muñoz, Mariano, additional, Andrés-León, Eduardo, additional, Ortega-Roldan, Jose Luis, additional, Seelig, Burckhard, additional, Ibarra-Molero, Beatriz, additional, and Sanchez-Ruiz, Jose M., additional

Published
2022
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8. Three-state molecular potentiometer based on a non-symmetrically positioned in-backbone linker

Author

Palomino-Ruiz, Lucía, primary, Reiné, Pablo, additional, R. Márquez, Irene, additional, Álvarez de Cienfuegos, Luis, additional, Agraït, Nicolás, additional, Cuerva, Juan M., additional, Campaña, Araceli G., additional, Leary, Edmund, additional, Miguel, Delia, additional, Millán, Alba, additional, Zotti, Linda A., additional, and González, M. Teresa, additional

Published
2021
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9. Extended enantiopure ortho-phenylene ethylene (o-OPE)-based helical systems as scaffolds for supramolecular architectures: a study of chiroptical response and its connection to the CISS effect

Author

Ortuño, Ana M., primary, Reiné, Pablo, additional, Resa, Sandra, additional, Álvarez de Cienfuegos, Luis, additional, Blanco, Victor, additional, Paredes, José Manuel, additional, Mota, Antonio J., additional, Mazzeo, Giuseppe, additional, Abbate, Sergio, additional, Ugalde, Jesus M., additional, Mujica, Vladimiro, additional, Longhi, Giovanna, additional, Miguel, Delia, additional, and Cuerva, Juan Manuel, additional

Published
2021
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10. Enantiopure Double ortho‐Oligophenylethynylene‐Based Helical Structures with Circularly Polarized Luminescence Activity.

Author

Reiné, Pablo, Ortuño, Ana M., Resa, Sandra, Álvarez de Cienfuegos, Luis, Ribagorda, María, Mota, Antonio J., Abbate, Sergio, Longhi, Giovanna, Miguel, Delia, and Cuerva, Juan M.

Subjects
*HELICAL structure, *LUMINESCENCE, *CIRCULAR dichroism, *ZINC catalysts, *COORDINATION polymers, *OPTICAL properties, *ISOMERS
Abstract

In this paper, we describe the optical and chiroptical properties of an enantiopure multipodal ortho‐oligophenylethynylene (S,S,S,S)‐1 presenting four chiral sulfoxide groups at the extremes. The presence of these groups together with alkynes allows the coordination with carbophilic Ag(I), and/or oxophilic Zn(II) cations, yielding double helical structures in an enantiopure way. In this sense, different behaviors in absorption, fluorescence, ECD and CPL spectra have been found depending on the stoichiometry and nature of the metal. We have observed that Zn(II) coordination favors an intensity increase of the electronic circular dichroism (ECD) spectra of compound (S,S,S,S)‐1 yielding an M‐helicity in the ortho‐oligophenylene ethynylene (o‐OPE) backbone. On the other hand, ECD spectra of final Ag(I) complex shows two different bands with an opposite sign to the free ligand, thus giving the P‐helical isomer. In addition, circularly polarized luminescence (CPL) exhibit an enhanced intensity and negative sign in both complexes. Computational studies were also carried out, supporting the experimental results. [ABSTRACT FROM AUTHOR]

Published
2022
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12. Pyrene-Containing ortho-Oligo(phenylene)ethynylene Foldamer as a Ratiometric Probe Based on Circularly Polarized Luminescence

Author

Reiné, Pablo, primary, Justicia, Jose, additional, Morcillo, Sara P., additional, Abbate, Sergio, additional, Vaz, Belen, additional, Ribagorda, María, additional, Orte, Ángel, additional, Álvarez de Cienfuegos, Luis, additional, Longhi, Giovanna, additional, Campaña, Araceli G., additional, Miguel, Delia, additional, and Cuerva, Juan M., additional

Published
2018
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13. OFF/ON switching of circularly polarized luminescence by oxophilic interaction of homochiral sulfoxide-containing o-OPEs with metal cations

Author

Reiné, Pablo, primary, Ortuño, Ana M., additional, Resa, Sandra, additional, Álvarez de Cienfuegos, Luis, additional, Blanco, Victor, additional, Ruedas-Rama, M. José, additional, Mazzeo, Giuseppe, additional, Abbate, Sergio, additional, Lucotti, Andrea, additional, Tommasini, Matteo, additional, Guisán-Ceinos, Santiago, additional, Ribagorda, Maria, additional, Campaña, Araceli G., additional, Mota, Antonio, additional, Longhi, Giovanna, additional, Miguel, Delia, additional, and Cuerva, Juan M., additional

Published
2018
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14. Exploring potentialities and limitations of stapledo-oligo(phenyleneethynylene)s (o-OPEs) as efficient circularly polarized luminescence emitters

Author

Reiné, Pablo, primary, Justicia, José, additional, Morcillo, Sara P., additional, Mazzeo, Giuseppe, additional, García-Fernández, Emilio, additional, Rodríguez-Diéguez, Antonio, additional, Álvarez de Cienfuegos, Luis, additional, Abbate, Sergio, additional, Cuerva, Juan M., additional, Longhi, Giovanna, additional, and Miguel, Delia, additional

Published
2017
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15. Exploring potentialities and limitations of stapled o-oligo(phenyleneethynylene)s ( o- OPEs) as efficient circularly polarized luminescence emitters.

Author

Reiné, Pablo, Justicia, José, Morcillo, Sara P., Mazzeo, Giuseppe, García‐Fernández, Emilio, Rodríguez‐Diéguez, Antonio, Álvarez de Cienfuegos, Luis, Abbate, Sergio, Cuerva, Juan M., Longhi, Giovanna, and Miguel, Delia

Subjects
*ETHYNYL compounds, *LUMINESCENCE, *CHIRALITY, *CIRCULAR dichroism, *DENSITY functional theory, *SUBSTITUENTS (Chemistry)
Abstract

In this paper, we have studied the chiroptical properties of a family of o-oligo(phenyleneethynylene) ( o-OPE) derivatives with different steric hindrance. Experimental results show high dissymmetry factors (gabs and glum up to 1.1 × 10−2) and very similar electronic circular dichroism (ECD) and circularly polarized luminescence (CPL) for all the derivatives that make this basic o-OPE scaffold a robust pure organic emitter. Vibrational circular dichroism spectra are used to characterize conformational properties in solution. Density functional theory and time-dependent density functional theory calculations support experimental results also proving that ECD and CPL are almost exclusively linked to helical moiety and not to size or conformation of substituents. As chiroptical properties of these emitters are independent of substituents, this OPE scaffold can be used as basic skeleton for the design of sensing probes with high CPL efficiencies. [ABSTRACT FROM AUTHOR]

Published
2018
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16. Chiral Single-Molecule Potentiometers Based on Stapled ortho- Oligo(phenylene)ethynylenes.

Author

Ortuño AM, Reiné P, Álvarez de Cienfuegos L, Márquez IR, Dednam W, Lombardi EB, Palacios JJ, Leary E, Longhi G, Mujica V, Millán A, González MT, Zotti LA, Miguel D, and Cuerva JM

Abstract

We report on the chemical design of chiral molecular junctions with stress-dependent conductance, whose helicity is maintained during the stretching of a single molecule junction due to the stapling of both ends of the inner helix. In the reported compounds, different conductive pathways are observed, with clearly different conductance values and plateau-length distributions, attributed to different conformations of the helical structures. The large chiro-optical responses and the potential use of these molecules as unimolecular spin filters have been theoretically proved using state-of-the-art Density Functional Theory (DFT) calculations, including a fully ab-initio estimation of the CISS-originating spin polarization which is done, for the first time, for a realistic molecular system., (© 2023 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.)

Published
2023
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