Publicaciones

Esta sección incluye una lista de los últimos artículos científicos del IPNA publicados en revistas incluidas en el Science Citation Index (SCI).

En DIGITAL.CSIC, repositorio institucional del CSIC, pueden encontrar el listado completo de artículos científicos desde 1962, así como otras colecciones de interés como congresos, tesis, libros, material divulgativo, etc. del centro. El objetivo de DIGITAL.CSIC es organizar, preservar y difundir en acceso abierto los resultados de nuestra investigación.

En el repositorio institucional del CSIC, pueden encontrar el listado completo de artículos científicos, así como otras colecciones de interés como congresos, tesis, libros, material divulgativo, etc.

Ir a Digital - CSIC

 

Análisis de la Producción Científica del IPNA 2014-2019: análisis bibliométrico realizado a partir de datos recogidos en Scopus y Web of Science.

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Digital CSIC

Priming effect of menadione sodium bisulphite against salinity stress in Arabidopsis involves epigenetic changes in genes controlling proline metabolism

Plants are able to develop numerous defence strategies to face stress. Amongst these, higher plants are capable of demonstrating stress imprint, a mechanism related with the phenomenon of priming. This is usually defined as genetic or biochemical modifications induced by a first stress exposure that leads to enhanced resistance to a later stress. Menadione sodium bisulphite (MSB), a water-soluble addition compound of vitamin K3, was first studied as a plant growth regulator and has been later widely shown to function as plant defence activator against several pathogens in a number of plant species. We recently reported that treating Arabidopsis seeds with MSB primes salt tolerance by inducing an early acclimation to salt stress. Here we describe the analysis of the effect of MSB on cytosine methylation in a salt stress background demonstrating that one of the mechanisms underlying this early acclimation to salt stress is an epigenetic mark. Specifically, MSB leads to a hypomethylation state at the promoter region of genes involved in the biosynthesis (P5CS1) and degradation (ERD5) of proline, affecting mainly CHG and CHH sites(where H is any nucleotide except G). The epigenetic changes detected are correlated with the observed expression patterns of P5CS1 (upregulation) and ERD5 (downregulation) genes and the increase in proline accumulation.

Jiménez-Arias, David; Borges, Andrés A.; Luis, Juan C.; Valdés, Francisco; Sandalio, Luisa M.; Pérez, José A.

Environmental and Experimental Botany 120: 23-30 (2015)
DOIDigital.CSIC

Microwave-Assisted Organocatalyzed Rearrangement of Propargyl Vinyl Ethers to Salicylaldehyde Derivatives: An Experimental and Theoretical Study

The microwave‐assisted imidazole‐catalyzed transformation of propargyl vinyl ethers (PVEs) into multisubstituted salicylaldehydes is described. The reaction is instrumentally simple, scalable, and tolerates a diverse degree of substitution at the propargylic position of the starting PVE. The generated salicylaldehyde motifs incorporate a broad range of topologies, spanning from simple aromatic monocycles to complex fused polycyclic systems. The reaction is highly regioselective and takes place under symmetry‐breaking conditions. The preparative power of this reaction was demonstrated in the first total synthesis of morintrifolin B, a benzophenone metabolite isolated from the small tree Morinda citrifolia L. A DFT study of the reaction was performed with full agreement between calculated values and experimental results. The theoretically calculated values support a domino mechanism comprising a propargyl Claisen rearrangement, a [1,3]‐H shift, a [1,7]‐H shift (enolization), a 6π electrocyclization, and an aromatization reaction.

Tejedor, David; Cotos, Leandro ; Márquez-Arce, Daniel; Odriozola-Gimeno, Mikel; Torrent-Sucarrat, Miquel; Cossío, Fernando P.; García-Tellado, Fernando

Chemistry - A European Journal 21(50): 18280-18289 (2015)
DOIDigital.CSIC

Prins Cyclization Catalyzed by a Fe(III)/TMS System: the Oxocarbenium Ion Pathway versus the [2+2] Cycloaddition

The different factors that control the alkene Prins cyclization catalyzed by iron(III) salts have been explored by means of a joint experimental–computational study. The iron(III) salt/trimethylsilyl halide system has proved to be an excellent promoter in the synthesis of crossed all‐cis disubstituted tetrahydropyrans, minimizing the formation of products derived from side‐chain exchange. In this iron(III)‐catalyzed Prins cyclization reaction between homoallylic alcohols and non‐activated alkenes, two mechanistic pathways can be envisaged, namely the classical oxocarbenium route and the alternative [2+2] cycloaddition‐based pathway. It is found that the [2+2] pathway is disfavored for those alcohols having non‐activated and non‐substituted alkenes. In these cases, the classical pathway, via the key oxocarbenium ion, is preferred. In addition, the final product distribution strongly depends upon the nature of the substituent adjacent to the hydroxy group in the homoallylic alcohol, which can favor or hamper a side 2‐oxonia‐Cope rearrangement.

Pérez, Sixto J.; Purino, Martín; Miranda, Pedro O.; Martín, Víctor S.; Fernández, Israel; Padrón, Juan I.

Chemistry - A European Journal 21(43): 15211-15217 (2015)
DOIDigital.CSIC

The 2014–2015 eruption of Fogo volcano: Geodetic modeling of Sentinel‐1 TOPS interferometry

After 20 years of quiescence, Fogo volcano erupted in November 2014. The eruption produced fast‐moving lava flows that traveled for several kilometers and destroyed two villages. This event represents the first episode of significant surface deformation imaged by the new European Space Agency's Sentinel‐1 satellite in its standard acquisition mode, Terrain Observation by Progressive Scans (TOPS), which differs from that of previous synthetic aperture radar (SAR) missions. We perform a Bayesian inversion of Sentinel‐1 TOPS SAR interferograms spanning the eruption and accurately account for variations in the TOPS line‐of‐sight vector when modeling displacements. Our results show that magma ascended beneath the Pico do Fogo cone and then moved laterally toward its southwestern flank, where the eruptive fissure opened. This study provides important insights into the inner workings of Fogo volcano and shows the potential of Sentinel‐1 TOPS interferometry for geophysical (e.g., volcano monitoring) applications.

González, Pablo J.; Bagnardi, Marco; Hooper, Andrew J.; Larsen, Yngvar; Marinkovic, Petar; Samsonov, Sergey V.; Wright, Tim J.

Geophysical Research Letter 42(21): 9239-9246 (2015)
DOI

Domino Process Achieves Site-Selective Peptide Modification with High Optical Purity. Applications to Chain Diversification and Peptide Ligation

The development of peptide libraries by site-selective modification of a few parent peptides would save valuable time and materials in discovery processes but still is a difficult synthetic challenge. Herein, we introduce natural hydroxyproline as a convertible unit for the production of a variety of optically pure amino acids, including expensive N-alkyl amino acids, homoserine lactones, and Agl lactams, and to achieve the mild, efficient, and site-selective modification of peptides. A domino process is used to cleave the customizable Hyp unit under mild, metal-free conditions. Both terminal and internal positions can be modified, and similar customizable units can be differentiated. The resulting products possess two reactive chains which can be manipulated independently. The versatility and scope of this process is highlighted by its application to the ligation of two peptide chains, and the generation of peptides with several chains and peptides with conformational restrictions.

Romero Estudillo, Iván Omar; Boto, Alicia

Journal of Organic Chemistry 80(19): 9379-9391 (2015)
DOIDigital.CSIC

Tanzawaic acids isolated from a marine-derived fungus of the genus Penicillium with cytotoxic activities

Tanzawaic acids M (1), N (2), O (3) and P (4) and the known tanzawaic acids B (5) and E (6), have been isolated from an extract of a cultured marine-derived fungus (strain CF07370) identified as a member of the genus Penicillium. The structures of 1–4 were determined based on spectroscopic evidence. The antimicrobial and cytotoxic activities of compounds 1–6 were evaluated.

Cardoso-Martínez, F.; Rosa, José M. de la; Díaz-Marrero, Ana R.; Darias, José; Cerella, Claudia; Diederich, Marc; Cueto, Mercedes

Organic and Biomolecular Chemistry 13(26): 7248-7256 (2015)
DOIDigital.CSIC

Chemoselective Intramolecular Functionalization of Methyl Groups in Nonconstrained Molecules Promoted by N-Iodosulfonamides

Mechanistic evidence observed in Hofmann–Löffler–Freytag-type reactions has been crucial to achieve the chemoselective functionalization of methyl groups under mild conditions. Radical-mediated methyl iodination and subsequent oxidative deiodination are the key steps in this functionalization, where iodine chemistry has a pivotal role on the formation of the C–N bond. The concepts of single hydrogen atom transfer (SHAT) and multiple hydrogen atom transfer (MHAT) are introduced to describe the observed chemoselectivity.

Paz, Nieves R.; Rodríguez Sosa, Dionisio; Valdés, Haydée; Marticorena, Ricardo; Melián, Daniel; Copano, Belén; González Martín, Concepción C.; Herrera, Antonio J.

Organic Letters 17(10): 2370-2373 (2015)
DOIDigital.CSIC

Oxidation with air by ascorbate-driven quinone redox cycling

Transition metal-free oxidation with air at room temperature has been achieved by simply using ascorbate (vitamin C) and catalytic amounts of menadione (vitamin K3). A combination of the mentioned vitamins transforms atmospheric oxygen into hydrogen peroxide, which is able to oxidize arylboronic acids and other chemical moieties.

G. Silveira-Dorta, D. M. Monzón, F. P. Crisóstomo, T. Martín, V. S. Martín, R. Carrillo

Chem. Commun, 51(32): 7027-7030 (2015)
DOIDigital.CSIC

Easy access to modified cyclodextrins by an intramolecular radical approach

A simple method to modify the primary face of cyclodextrins (CDs) is described. The 6I‐O‐yl radical of α‐, β‐, and γ‐CDs regioselectively abstracts the H5II, located in the adjacent D‐glucose unit, by an intramolecular 1,8‐hydrogen‐atom‐transfer reaction through a geometrically restricted nine‐membered transition state to give a stable 1,3,5‐trioxocane ring. The reaction has been extended to the 1,4‐diols of α‐ and β‐CD to give the corresponding bis(trioxocane)s. The C2‐symmetric bis(trioxocane) corresponding to the α‐CD is a stable crystalline solid whose structure was confirmed by X‐ray diffraction analysis. The calculated geometric parameters confirm that the primary face is severely distorted toward a narrower elliptical shape for this rim.

Álvarez-Dorta, Dimitri; León, Elisa I.; Kennedy, Alan R.; Martín, Ángeles; Pérez-Martín, Inés; Suárez, Ernesto

Angewandte Chemie International Edition 54(12): 3674-3678 (2015)
DOIDigital.CSIC

Synthesis of New Benzocyclotrimer Analogues: New Receptors for Tetramethylammonium Ion Recognition

Using a [2 + 2 + 2] cycloaddition/Mitsunobu reaction sequence, a convenient synthesis to access new benzocyclotrimer analogues has been developed. The new receptors have the geometry and functionality capable of recognizing the tetramethylammonium ion in the gas phase and in solution.

Carrillo Fumero, Romen; Hynes, Michael J.; Martín, Víctor S.; Martín, Tomás; Pinacho Crisóstomo, Fernando R.

Organic Letters 17(12): 2912-2915 (2015)
DOIDigital.CSIC