2026-04-17T19:12:24Zhttps://uvadoc.uva.es/oai/request

oai:uvadoc.uva.es:10324/509402022-02-01T12:02:56Zcom_10324_1186com_10324_931com_10324_894col_10324_1404

Saragi, Rizalina Tama Juanes San José, Marcos Abad, José Luis Pinacho Gómez, Ruth Rubio García, José Emiliano Lesarri Gómez, Alberto Eugenio 2022 Producción Científica 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. application/pdf https://uvadoc.uva.es/handle/10324/50940 eng Elsevier Chirality-Puckering correlation and intermolecular interactions in Sphingosines: Rotational spectroscopy of jaspine B3 and its monohydrate info:eu-repo/semantics/article TEXT UVaDOC. Repositorio Documental de la Universidad de Valladolid Hispana