The complexation properties of some unnatural and natural macrocyclic trichothecenes

Derek W. Anderson; Peter R. Ashton; Robin M. Black; David A. Leigh; Alexandra M Z Slawin; J. Fraser Stoddart; David J. Williams

doi:10.1039/C39880000904

The complexation properties of some unnatural and natural macrocyclic trichothecenes

Derek W. Anderson^*, Peter R. Ashton, Robin M. Black, David A. Leigh, Alexandra M Z Slawin, J. Fraser Stoddart, David J. Williams

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

12 Scopus citations

Abstract

As a result of investigating the complexing properties of a series of novel polyether analogues (3)-(9) of macrocyclic trichothecenes towards alkali metal cations and RNH₃⁺ ions, it has been proposed, with supporting evidence from X-ray crystallography on verrucarin A (1) and fast atom bombardment mass spectrometry of complexes involving (1) and the triacetate (10) of baccharinol B4 (11), that the enhanced biological activities of macrocyclic trichothecenes, such as (1) and (11), compared with non-macrocyclic trichoverroids such as (2), may be a consequence of their abilities to bind to NH₃⁺ ionic sites on proteins, particularly those associated with the 60S ribosomes.

Original language	English (US)
Pages (from-to)	904-908
Number of pages	5
Journal	Journal of the Chemical Society, Chemical Communications
Issue number	13
DOIs	https://doi.org/10.1039/C39880000904
State	Published - 1988

ASJC Scopus subject areas

Molecular Medicine

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title = "The complexation properties of some unnatural and natural macrocyclic trichothecenes",

abstract = "As a result of investigating the complexing properties of a series of novel polyether analogues (3)-(9) of macrocyclic trichothecenes towards alkali metal cations and RNH3+ ions, it has been proposed, with supporting evidence from X-ray crystallography on verrucarin A (1) and fast atom bombardment mass spectrometry of complexes involving (1) and the triacetate (10) of baccharinol B4 (11), that the enhanced biological activities of macrocyclic trichothecenes, such as (1) and (11), compared with non-macrocyclic trichoverroids such as (2), may be a consequence of their abilities to bind to NH3+ ionic sites on proteins, particularly those associated with the 60S ribosomes.",

author = "Anderson, {Derek W.} and Ashton, {Peter R.} and Black, {Robin M.} and Leigh, {David A.} and Slawin, {Alexandra M Z} and Stoddart, {J. Fraser} and Williams, {David J.}",

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AU - Anderson, Derek W.

AU - Ashton, Peter R.

AU - Black, Robin M.

AU - Leigh, David A.

AU - Slawin, Alexandra M Z

AU - Stoddart, J. Fraser

AU - Williams, David J.

PY - 1988

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N2 - As a result of investigating the complexing properties of a series of novel polyether analogues (3)-(9) of macrocyclic trichothecenes towards alkali metal cations and RNH3+ ions, it has been proposed, with supporting evidence from X-ray crystallography on verrucarin A (1) and fast atom bombardment mass spectrometry of complexes involving (1) and the triacetate (10) of baccharinol B4 (11), that the enhanced biological activities of macrocyclic trichothecenes, such as (1) and (11), compared with non-macrocyclic trichoverroids such as (2), may be a consequence of their abilities to bind to NH3+ ionic sites on proteins, particularly those associated with the 60S ribosomes.

AB - As a result of investigating the complexing properties of a series of novel polyether analogues (3)-(9) of macrocyclic trichothecenes towards alkali metal cations and RNH3+ ions, it has been proposed, with supporting evidence from X-ray crystallography on verrucarin A (1) and fast atom bombardment mass spectrometry of complexes involving (1) and the triacetate (10) of baccharinol B4 (11), that the enhanced biological activities of macrocyclic trichothecenes, such as (1) and (11), compared with non-macrocyclic trichoverroids such as (2), may be a consequence of their abilities to bind to NH3+ ionic sites on proteins, particularly those associated with the 60S ribosomes.

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The complexation properties of some unnatural and natural macrocyclic trichothecenes

Abstract

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