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.

Marine Drugs
Anna AielloRocco Vitalone

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.

References

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Apr 1, 2010·Journal of Natural Products·Anna AielloRocco Vitalone

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Citations

Aug 22, 2013·Progress in Nuclear Magnetic Resonance Spectroscopy·Teodor Parella, Juan Félix Espinosa
Jun 4, 2014·Chemistry : a European Journal·Sébastien AlazetThierry Billard
Dec 18, 2014·Chemical Reviews·Svetlana A VizerValery M Dembitsky
Jun 9, 2016·International Journal of Molecular Sciences·Mauricio SotoLautaro Taborga
Oct 30, 2012·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Concetta ImperatoreMarialuisa Menna
Sep 25, 2018·Natural Product Reports·Marialuisa MennaOrazio Taglialatela-Scafati
Jun 6, 2019·Natural Product Reports·Laura GrausoAlfonso Mangoni
Jan 7, 2014·Natural Product Reports·John W BluntMichèle R Prinsep
Aug 23, 2020·Antibiotics·Marcello CasertanoConcetta Imperatore
May 21, 2021·Planta medica·Junchi WangJianyong Si

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Methods Mentioned

BETA
NMR

Software Mentioned

PCM
GAUSSIAN
ROESY
Gaussian03
IEF

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