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

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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., ... 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

Metal binding of Lissoclinum patella metabolites. Part 2: Lissoclinamides 9 and 10. / Morris, L. A.; Milne, B. R.; Jaspars, Marcel; Kettenes-van den Bosch, J. J.; Versluis, K.; Heck, A. J. R.; Kelly, S. M.; Price, N. C.

In: Tetrahedron, Vol. 57, No. 15, 2001, p. 3199-3207.

Research output: Contribution to journalArticle

Morris, LA, Milne, BR, Jaspars, M, Kettenes-van den Bosch, JJ, Versluis, K, Heck, AJR, Kelly, SM & Price, NC 2001, 'Metal binding of Lissoclinum patella metabolites. Part 2: Lissoclinamides 9 and 10', Tetrahedron, vol. 57, no. 15, pp. 3199-3207. https://doi.org/10.1016/S0040-4020(01)00178-8
Morris LA, Milne BR, Jaspars M, Kettenes-van den Bosch JJ, Versluis K, Heck AJR et al. Metal binding of Lissoclinum patella metabolites. Part 2: Lissoclinamides 9 and 10. Tetrahedron. 2001;57(15):3199-3207. https://doi.org/10.1016/S0040-4020(01)00178-8
Morris, L. A. ; Milne, B. R. ; Jaspars, Marcel ; Kettenes-van den Bosch, J. J. ; Versluis, K. ; Heck, A. J. R. ; Kelly, S. M. ; Price, N. C. / Metal binding of Lissoclinum patella metabolites. Part 2: Lissoclinamides 9 and 10. In: Tetrahedron. 2001 ; Vol. 57, No. 15. pp. 3199-3207.
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