Metal binding of Lissoclinum patella metabolites. Part 2: Lissoclinamides 9 and 10

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

Research output: Contribution to journalArticle

33 Citations (Scopus)

Abstract

Studies on the Thz, Thn and Oxn containing cyclic peptides, lissoclinamides 9 (9) and 10 (10) isolated from the Indo-Pacific ascidian (seasquirt) Lissoclinum patella have delineated their metal binding selectivity. MS and CD competition studies show that lissoclinamide 10 (10) shows selectivity for Cu2+ in the presence of an excess of Zn2+ whereas lissoclinamide 9 (9) is less selective for Cu2+. Comparison of the solution state conformations derived from nOe restrained molecular dynamics and additional Monte-Carlo conformational searches suggested binding environments for the Cu2+ which confirmed the MS measurements and suggested a reason for the selectivity in the case of lissoclinamides 9 and 10. (C) 2001 Elsevier Science Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)3199-3207
Number of pages8
JournalTetrahedron
Volume57
Issue number15
DOIs
Publication statusPublished - 2001

Keywords

  • complexation
  • natural products
  • circular dichroism
  • mass spectrometry
  • CYCLIC-PEPTIDES

Cite this

Morris, L. A., Milne, B. R., Jaspars, M., Kettenes-van den Bosch, J. J., Versluis, K., Heck, A. J. R., Kelly, S. M., & Price, N. C. (2001). Metal binding of Lissoclinum patella metabolites. Part 2: Lissoclinamides 9 and 10. Tetrahedron, 57(15), 3199-3207. https://doi.org/10.1016/S0040-4020(01)00178-8