Structure determination and MSn analysis of two new lissoclinamides isolated from the Indo-Pacific ascidian Lissoclinum patella: NOE restrained molecular dynamics confirms the absolute stereochemistry derived by degradative methods

L A Morris, J J K van den Bosch, K Versluis, G S Thompson, M Jaspars

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Abstract

Two new lissoclinamides, lissoclinamides 9 and 10 were isolated from an Indonesian collection of the ascidian Lissoclinum patella along with the known patellamide C. The structures of the lissoclinamides were determined by a combination of 2D NMR, selective 1D TOCSY, MS and MSn techniques. The assignment of absolute stereochemistry was achieved by the hydrolysis of lissoclinamides 9 and 10 followed by chiral TLC. In the case of lissoclinamide 9, NOE restrained molecular dynamics studies were also performed confirming the proposed stereochemistry. (C) 2000 Elsevier Science Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)8345-8353
Number of pages9
JournalTetrahedron
Volume56
Issue number42
DOIs
Publication statusPublished - 2000

Keywords

  • lissoclinamide
  • patellamide C
  • stereochemistry
  • CYTO-TOXIC ACTIVITY
  • CYCLIC-PEPTIDES
  • MASS-SPECTROMETRY
  • SPECTROSCOPY
  • NMR
  • METABOLITES
  • TUNICATE

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