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    Por favor, use este identificador para citar o enlazar este ítem:https://uvadoc.uva.es/handle/10324/50940

    Título
    Chirality-Puckering correlation and intermolecular interactions in Sphingosines: Rotational spectroscopy of jaspine B3 and its monohydrate
    Autor
    Saragi, Rizalina TamaAutoridad UVA
    Juanes San José, MarcosAutoridad UVA
    Abad, José Luis
    Pinacho Gómez, RuthAutoridad UVA Orcid
    Rubio García, José EmilianoAutoridad UVA Orcid
    Lesarri Gómez, Alberto EugenioAutoridad UVA Orcid
    Año del Documento
    2022
    Editorial
    Elsevier
    Descripción
    Producción Científica
    Documento Fuente
    Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2022, vol. 267, part 2, 120531
    Resumo
    Chirality is determinant for sphingosine biofunctions and pharmacological activity, yet the reasons for the biological chiral selection are not well understood. Here, we characterized the intra- and intermolecular interactions at the headgroup of the cytotoxic anhydrophytosphingosine jaspine B, revealing chirality-dependent correlations between the puckering of the ring core and the formation of amino-alcohol hydrogen bond networks, both in the monomer and the monohydrate. Following the specific synthesis of a shortened 3-carbon side-chain molecule, denoted jaspine B3, six different isomers were observed in a jet expansion using broadband (chirped-pulsed) rotational spectroscopy. Additionally, a single isomer of the jaspine B3 monohydrate was observed, revealing the insertion of water in between the hydroxy and amino groups and the formation of a network of O-H···N-H···Oring hydrogen bonds. The specific jaspine B3 stereochemistry thus creates a double-faced molecule where the exposed lone-pair electrons may easily catalyze the formation of intermolecular aggregates and determine the sphingosine biological properties.
    Palabras Clave
    Noncovalent interactions
    Interacciones no covalentes
    Sphingosines
    Esfingosina
    Rotational spectroscopy
    Espectroscopía rotacional
    ISSN
    1386-1425
    Revisión por pares
    SI
    DOI
    10.1016/j.saa.2021.120531
    Patrocinador
    Ministerio de Ciencia, Innovación y Universidades - Fondo Europeo de Desarrollo Regional (grant PGC2018-098561-B-C22)
    Version del Editor
    https://www.sciencedirect.com/science/article/pii/S1386142521011082?via%3Dihub
    Propietario de los Derechos
    © 2021 The Authors
    Idioma
    eng
    URI
    https://uvadoc.uva.es/handle/10324/50940
    Tipo de versión
    info:eu-repo/semantics/publishedVersion
    Derechos
    openAccess
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    Universidad de Valladolid

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