Metal binding of Lissclinum patella metabolites. Part 1: Patellamides A, C and ulithiacyclamide A

L. A. Morris, Marcel Jaspars, J. J. Kettenes-van den Bosch, K. Versluis, A. J. R. Heck, S. M. Kelly, N. C. Price

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Abstract

Studies on three Thz, and Oxn containing cyclic peptides, patellamide A and C (1, 3) and ulithiacyclamide A (9) isolated from the Indo-Pacific ascidian (seasquirt) Lissoclinum patella have delineated their metal binding selectivity. Patellamide C (3) shows extreme selectivity for Cu2+ even in the presence of an excess of Zn2+ and shows no binding at all to Co2+, Ni2+ and Hg2+. Patellamide A (1) is less selective for Cu2+, whereas ulithiacyclamide A (9) shows selectivity similar to that of patellamide C (3). The selectivity was studied by circular dichroism spectroscopy and mass spectrometry. The CD spectra obtained whilst patellamide C was slowly titrated with CU2+ show one isosbestic point indicating the CU2+ binding involves only two conformations. These studies indicate that CU2+, not Zn2+ is the biologically relevant metal for these compounds and point towards a potential ecological function of these complexes. (C) 2001 Elsevier Science Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)3185-3197
Number of pages12
JournalTetrahedron
Volume57
Issue number15
DOIs
Publication statusPublished - 2001

Keywords

  • complexation
  • natural products
  • circular dichroism
  • mass spectrometry
  • CYCLIC-PEPTIDES
  • MOLECULAR-DYNAMICS
  • NMR-SPECTROSCOPY
  • ASCIDIACYCLAMIDE
  • OCTAPEPTIDE
  • COPPER(II)
  • TUNICATE

Cite this

Morris, L. A., Jaspars, M., Kettenes-van den Bosch, J. J., Versluis, K., Heck, A. J. R., Kelly, S. M., & Price, N. C. (2001). Metal binding of Lissclinum patella metabolites. Part 1: Patellamides A, C and ulithiacyclamide A. Tetrahedron, 57(15), 3185-3197. https://doi.org/10.1016/S0040-4020(01)00177-6