Conformational studies of free and Li+ complexed jasplakinolide, a cyclic depsipeptide from the Fijian marine sponge Jaspis splendens

Jioji N. Tabudravu; Linda A. Morris; Bruce F. Milne; Marcel Jaspars

doi:10.1039/B416839A

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Conformational studies of free and Li⁺ complexed jasplakinolide, a cyclic depsipeptide from the Fijian marine sponge Jaspis splendens†

Jioji N. Tabudravu,^a Linda A. Morris,^b Bruce F. Milne^a and Marcel Jaspars*^a

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* Corresponding authors

^a Marine Natural Products Laboratory, Department of Chemistry, University of Aberdeen, Scotland, UK
E-mail: m.jaspars@abdn.ac.uk
Fax: +44 1224 272921
Tel: +44 1224 272895

^b Division of Biological Chemistry and Molecular Microbiology, University of Dundee, Scotland, UK

Abstract

The complexation of Li⁺ to jasplakinolide, a marine sponge derived cyclic depsipeptide showed preferential binding to two out of four carbonyl oxygens (C-10, C-14) and the electrons of the aromatic system of the β-tyrosine amino acid residue. This is in contrast to previous results obtained by others who proposed complexation to three out of four available carbonyl oxygens (C-1, C-10, C-14). The structure of the complex in CD₃CN was determined by NOE restrained molecular dynamic calculations. Structures of the uncomplexed jasplakinolide were calculated in CDCl₃ and CD₃CN for comparison.

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Supplementary files

Table S1: ¹H and ¹³C NMR data of jasplakinolide in CDCl ₃ and CD ₃CN at 400/100 MHz. Table S2: ¹H, ¹³C NMR, ¹H– ¹H COSY and HMBC data at 400/100 MHz and literature ¹³C NMR data ²⁰ of jasplakinolide–Li ⁺ complex in CD ₃CN. Table S3: ¹³C Chemical shift differences between jasplinolide and jasplakinolide–Li ⁺ complex in CD ₃CN. Table S4: Restraints used for NOE restrained structure calculation of jasplakinolide in CDCl ₃. Table S5: Torsion angle restraints for jasplakinolide in CDCl ₃. Table S6: Energies (kcal mol ⁻¹) for jasplakinolide minimum energy structure in CDCl ₃. Table S7: Statistics for 22 lowest energy structures of jasplakinolide in CDCl ₃. Table S8: Restraints used for NOE restrained structure calculation of jasplakinolide in CD ₃CN. Table S9: Torsion angle restraints for jasplakinolide in CD ₃CN. Table S10: Energies (kcal mol ⁻¹) for jasplakinolide minimum energy structure in CD ₃CN. Table S11: Statistics for the 19 lowest energy structures of jasplakinolide in CD ₃CN. Table S12: Restraints used for NOE restrained structure calculation of the jasplakinolide–Li ⁺ complex in CD ₃CN. Table S13: Torsion angle restraints for jasplakinolide–Li ⁺ complex in CD ₃CN. Table S14: Energies (kcal mol ⁻¹) for jasplakinolide–Li ⁺ complex minimum energy structure in CD ₃CN. Table S15: Statistics for the 35 lowest energy structures of jasplakinolide–Li ⁺ complex in CD ₃CN PDF (171K)

Article information

DOI: https://doi.org/10.1039/B416839A
Article type: Paper
Submitted: 05 Nov 2004
Accepted: 18 Jan 2005
First published: 07 Feb 2005

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Org. Biomol. Chem., 2005,3, 745-749

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Conformational studies of free and Li⁺ complexed jasplakinolide, a cyclic depsipeptide from the Fijian marine sponge Jaspis splendens

J. N. Tabudravu, L. A. Morris, B. F. Milne and M. Jaspars, Org. Biomol. Chem., 2005, 3, 745 DOI: 10.1039/B416839A

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Organic & Biomolecular Chemistry