Molinski, Tadeusz F. Biegelmeyer, Renata Stout, E. Paige Wang, Xiao L. C. Frota, Mario Henriques, Amelia T. Halisphingosines A and B, Modified Sphingoid Bases from <i>Haliclona tubifera</i>. Assignment of Configuration by Circular Dichroism and van’t Hoff’s Principle of Optical Superposition Halisphingosines A (<b>1</b>) and B (<b>2</b>), modified long-chain sphingoid bases, from the marine sponge <i>Haliclona tubifera</i> collected in Brazil, were characterized after conversion to their <i>N</i>-Boc derivatives. The 2<i>R</i>,3<i>R</i>,6<i>R</i> configuration of halisphingosine A, a compound first reported from <i>Haliclona</i> sp. from South Korea, was confirmed using a novel CD approach: deconvolution of exciton coupling from mono- and trinaphthoyl derivatives obtained by derivatization of the natural product. The sensitive CD deconvolution method, applicable to submilligram samples, simultaneously predicted the relative and absolute configuration of three stereocenters in halisphingosine A with precision and accuracy. Halisphingosine B was assigned by correlation to halisphingosine A. Circular Dichroism;Optical SuperpositionHalisphingosines;configuration;submilligram samples;Haliclona sp;trinaphthoyl derivatives;halisphingosine;novel CD approach;marine sponge Haliclona tubifera;Modified Sphingoid Bases;Haliclona tubifera;CD deconvolution method;Halisphingosine B 2013-03-22
    https://acs.figshare.com/articles/journal_contribution/Halisphingosines_A_and_B_Modified_Sphingoid_Bases_from_i_Haliclona_tubifera_i_Assignment_of_Configuration_by_Circular_Dichroism_and_van_t_Hoff_s_Principle_of_Optical_Superposition/2431954
10.1021/np300744y.s001