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

Research output: Contribution to journalArticle

37 Citations (Scopus)

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

Cite this

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title = "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",
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.",
keywords = "lissoclinamide, patellamide C, stereochemistry, CYTO-TOXIC ACTIVITY, CYCLIC-PEPTIDES, MASS-SPECTROMETRY, SPECTROSCOPY, NMR, METABOLITES, TUNICATE",
author = "Morris, {L A} and {van den Bosch}, {J J K} and K Versluis and Thompson, {G S} and M Jaspars",
year = "2000",
doi = "10.1016/S0040-4020(00)00746-8",
language = "English",
volume = "56",
pages = "8345--8353",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "PERGAMON-ELSEVIER SCIENCE LTD",
number = "42",

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TY - JOUR

T1 - Structure determination and MSn analysis of two new lissoclinamides isolated from the Indo-Pacific ascidian Lissoclinum patella

T2 - NOE restrained molecular dynamics confirms the absolute stereochemistry derived by degradative methods

AU - Morris, L A

AU - van den Bosch, J J K

AU - Versluis, K

AU - Thompson, G S

AU - Jaspars, M

PY - 2000

Y1 - 2000

N2 - 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.

AB - 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.

KW - lissoclinamide

KW - patellamide C

KW - stereochemistry

KW - CYTO-TOXIC ACTIVITY

KW - CYCLIC-PEPTIDES

KW - MASS-SPECTROMETRY

KW - SPECTROSCOPY

KW - NMR

KW - METABOLITES

KW - TUNICATE

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U2 - 10.1016/S0040-4020(00)00746-8

DO - 10.1016/S0040-4020(00)00746-8

M3 - Article

VL - 56

SP - 8345

EP - 8353

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 42

ER -