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

doi:10.1016/S0040-4020(00)00746-8

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

Chemistry

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39 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 language	English
Pages (from-to)	8345-8353
Number of pages	9
Journal	Tetrahedron
Volume	56
Issue number	42
DOIs	https://doi.org/10.1016/S0040-4020(00)00746-8
Publication status	Published - 2000

Keywords

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

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Morris, L. A., van den Bosch, J. J. K., Versluis, K., Thompson, G. S., & Jaspars, M. (2000). 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. Tetrahedron, 56(42), 8345-8353. https://doi.org/10.1016/S0040-4020(00)00746-8

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. / Morris, L A ; van den Bosch, J J K ; Versluis, K et al.
In: Tetrahedron, Vol. 56, No. 42, 2000, p. 8345-8353.

Research output: Contribution to journal › Article

Morris, LA, van den Bosch, JJK, Versluis, K, Thompson, GS & Jaspars, M 2000, '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', Tetrahedron, vol. 56, no. 42, pp. 8345-8353. https://doi.org/10.1016/S0040-4020(00)00746-8

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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.",

keywords = "lissoclinamide, patellamide C, stereochemistry, CYTO-TOXIC ACTIVITY, CYCLIC-PEPTIDES, MASS-SPECTROMETRY, SPECTROSCOPY, NMR, METABOLITES, TUNICATE",

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AU - Thompson, G S

AU - Jaspars, M

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KW - stereochemistry

KW - CYTO-TOXIC ACTIVITY

KW - CYCLIC-PEPTIDES

KW - MASS-SPECTROMETRY

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KW - METABOLITES

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ER -

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

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Keywords

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