Volume 31, Issue 5
Natural Products
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ChemInform Abstract: Synthesis of Two Stable Nitrogen Analogues of S-Adenosyl-L-methionine.

Mark J. Thompson

Mark J. Thompson

Dep. Chem., Univ. Sheffield, Sheffield S3 7HF, UK

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Abdelaziz Mekhalfia

Abdelaziz Mekhalfia

Dep. Chem., Univ. Sheffield, Sheffield S3 7HF, UK

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David P. Hornby

David P. Hornby

Dep. Chem., Univ. Sheffield, Sheffield S3 7HF, UK

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G. Michael Blackburn

G. Michael Blackburn

Dep. Chem., Univ. Sheffield, Sheffield S3 7HF, UK

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First published: 11 June 2010

Abstract

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ChemInform Abstract

The homochiral syntheses of both title compounds, methylamine analogue (I) and previously unreported dimethylammonium analogue (II), are described. Compound (I) is a charge-switchable analogue of S-adenosyl-L-methionine whose ionic state is a function of the pH whereas the ionic state of compound (II) is pH-independent. The affinities of both analogues for a range of proteins are under investigation.

chemical structure image

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