ArticleJournal of natural products2013
Halisphingosines A and B, modified sphingoid bases from Haliclona tubifera. Assignment of configuration by circular dichroism and van't Hoff's principle of optical superposition.
Article in Journal of natural products, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed.
- Structure Revision of Halisphingosine A via Total Synthesis and Bioactivity Studies.Angewandte Chemie (International ed. in English) · 2024Article
- Potential of Polar Lipids Isolated from the Marine SpongeInternational journal of molecular sciences · 2024Article
- National Cancer Institute (NCI) Program for Natural Products Discovery: Rapid Isolation and Identification of Biologically Active Natural Products from the NCI Prefractionated Library.ACS chemical biology · 2020Article
- Enantiomeric Variability of Distaminolyne A. Refinement of ECD and NMR Methods for Determining Optical Purity of 1-Amino-2-Alkanols.Molecules (Basel, Switzerland) · 2018Article
- Six Trikentrin-like Cyclopentanoindoles from Trikentrion flabelliforme. Absolute Structural Assignment by NMR and ECD.The Journal of organic chemistry · 2018Article
- Liposomal Circular Dichroism (L-CD) of Arenoyl Derivatives of Sphingolipids. Amplification of Cotton Effects in Ordered Lipid Bilayers.Marine drugs · 2017Article
- Isolation and Synthesis of a Bacterially Produced Inhibitor of Rosette Development in Choanoflagellates.Journal of the American Chemical Society · 2016Article
- Sphingosines Derived from Marine Sponge as Potential Multi-Target Drug Related to Disorders in Cancer Development.Marine drugs · 2015Article
- D-Glucosamine-derived synthons for assembly of L-threo-sphingoid bases. Total synthesis of rhizochalinin C.The Journal of organic chemistry · 2013Article
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Authors and funding
6 authors.
Funding
Abstract
Halisphingosines A (1) and B (2), modified long-chain sphingoid bases, from the marine sponge Haliclona tubifera collected in Brazil, were characterized after conversion to their N-Boc derivatives. The 2R,3R,6R configuration of halisphingosine A, a compound first reported from Haliclona 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.
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