title: Aplisulfamines, new sulfoxide-containing metabolites from an aplidium tunicate: absolute stereochemistry at chiral sulfur and carbon atoms assigned through an original combination of spectroscopic and computational methods.
abstract: Two new sulfoxide-containing metabolites, aplisulfamines A and B, have been isolated from an Aplidium sp. collected in the Bay of Naples. Their planar structure and geometry of a double bond were readily determined by using standard methods, mainly NMR spectroscopy. An original approach was used to assign the absolute configuration at the three contiguous chiral centers present in the structures of both aplisulfamines, two at carbon and one at sulfur. This involved Electronic Circular Dichroism (ECD) studies, J-based configuration analysis and Density Functional Theory (DFT) calculations and represents an interesting integration of modern techniques in stereoanalysis, which could contribute to the enhancement of theoretical protocols recently applied to solve stereochemical aspects in structure elucidation.
authors.affiliation: The NeaNat Group, Dipartimento di Chimica delle Sostanze Naturali, Università degli Studi di Napoli "Federico II", Via D. Montesano 49, 80131 Napoli, Italy.
authors.forename: Anna
authors.initials: A
authors.lastname: Aiello
authors.affiliation: The NeaNat Group, Dipartimento di Chimica delle Sostanze Naturali, Università degli Studi di Napoli "Federico II", Via D. Montesano 49, 80131 Napoli, Italy.
authors.forename: Ernesto
authors.initials: E
authors.lastname: Fattorusso
authors.affiliation: The NeaNat Group, Dipartimento di Chimica delle Sostanze Naturali, Università degli Studi di Napoli "Federico II", Via D. Montesano 49, 80131 Napoli, Italy.
authors.forename: Concetta
authors.initials: C
authors.lastname: Imperatore
authors.affiliation: C.S.I.A.S. (Centro Servizi Interuniversitario di Analisi Strumentale), Università degli Studi di Napoli "Federico II", Via D. Montesano 49, 80131 Napoli, Italy.
authors.forename: Paolo
authors.initials: P
authors.lastname: Luciano
authors.affiliation: The NeaNat Group, Dipartimento di Chimica delle Sostanze Naturali, Università degli Studi di Napoli "Federico II", Via D. Montesano 49, 80131 Napoli, Italy.
authors.forename: Marialuisa
authors.identifier: 0000-0002-4515-3014
authors.initials: M
authors.lastname: Menna
authors.affiliation: The NeaNat Group, Dipartimento di Chimica delle Sostanze Naturali, Università degli Studi di Napoli "Federico II", Via D. Montesano 49, 80131 Napoli, Italy.
authors.forename: Rocco
authors.initials: R
authors.lastname: Vitalone
mesh_terms: D000818:Animals; D002244:Carbon / Q000737:chemistry; D002942:Circular Dichroism; D008968:Molecular Conformation; D019906:Nuclear Magnetic Resonance, Biomolecular; D013454:Sulfoxides / Q000737:chemistry*; D013455:Sulfur / Q000737:chemistry; D014561:Urochordata / Q000378:metabolism*
chemical_list: D013454:Sulfoxides; C573080:aplisulfamine A; C573081:aplisulfamine B; D013455:Sulfur; D002244:Carbon