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

doi:10.1016/S0040-4020(01)00178-8

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

Chemistry

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34 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 language	English
Pages (from-to)	3199-3207
Number of pages	8
Journal	Tetrahedron
Volume	57
Issue number	15
DOIs	https://doi.org/10.1016/S0040-4020(01)00178-8
Publication status	Published - 2001

Keywords

complexation
natural products
circular dichroism
mass spectrometry
CYCLIC-PEPTIDES

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10.1016/S0040-4020(01)00178-8

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@article{59784fe9deab444887df31e2d05f00f6,

title = "Metal binding of Lissoclinum patella metabolites. Part 2: Lissoclinamides 9 and 10",

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.",

keywords = "complexation, natural products, circular dichroism, mass spectrometry, CYCLIC-PEPTIDES",

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

year = "2001",

doi = "10.1016/S0040-4020(01)00178-8",

language = "English",

volume = "57",

pages = "3199--3207",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "PERGAMON-ELSEVIER SCIENCE LTD",

number = "15",

}

TY - JOUR

T1 - Metal binding of Lissoclinum patella metabolites. Part 2: Lissoclinamides 9 and 10

AU - Morris, L. A.

AU - Milne, B. R.

AU - Jaspars, Marcel

AU - Kettenes-van den Bosch, J. J.

AU - Versluis, K.

AU - Heck, A. J. R.

AU - Kelly, S. M.

AU - Price, N. C.

PY - 2001

Y1 - 2001

N2 - 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.

AB - 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.

KW - complexation

KW - natural products

KW - circular dichroism

KW - mass spectrometry

KW - CYCLIC-PEPTIDES

U2 - 10.1016/S0040-4020(01)00178-8

DO - 10.1016/S0040-4020(01)00178-8

M3 - Article

VL - 57

SP - 3199

EP - 3207

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 15

ER -

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

Abstract

Keywords

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