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Issue 3, 2006
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Synthesis of trimethyl (2S,3R)- and (2R,3R)-[2-2H1]-homocitrates and dimethyl (2S,3R)- and (2R,3R)-[2-2H1]-homocitrate lactones—an assay for the stereochemical outcome of the reaction catalysed both by homocitrate synthase and by the Nif-V protein

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Abstract

Trimethyl (3R)-homocitrate 17, trimethyl (2S,3R)-[2-2H1]-homocitrate 17a and (2R,3R)-[2-2H1]-homocitrate 17b, as well as dimethyl (3R)-homocitrate lactone 18, (2S,3R)-[2-2H1]-homocitric lactone 18a and (2R,3R)-[2-2H1]-homocitric lactone 18b have been synthesised. D-Quinic acid 12 was used as the source of the (3R)-centre in the unlabelled target compounds 17 and 18. (−)-Shikimic acid 19 and the (−)-[2-2H]-shikimic acid derivative 32 respectively were used in the synthesis of the labelled compounds. In the latter syntheses, Sharpless directed epoxidation of the olefin in the 5-deoxy ester diols 23 and 35 ensured a reaction from the same face as the allylic and homoallylic alcohols, and the reduction of the protected epoxides 25 and 37 ensured that the label was introduced in a stereoselective manner. The 1H NMR spectra of the labelled products present an assay for the stereochemistry of the biological reactions catalysed by homocitrate synthase and by the protein from the nifV gene.

Graphical abstract: Synthesis of trimethyl (2S,3R)- and (2R,3R)-[2-2H1]-homocitrates and dimethyl (2S,3R)- and (2R,3R)-[2-2H1]-homocitrate lactones—an assay for the stereochemical outcome of the reaction catalysed both by homocitrate synthase and by the Nif-V protein

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Publication details

The article was received on 09 Nov 2005, accepted on 01 Dec 2005 and first published on 06 Jan 2006


Article type: Paper
DOI: 10.1039/B515937G
Citation: Org. Biomol. Chem., 2006,4, 569-580
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    Synthesis of trimethyl (2S,3R)- and (2R,3R)-[2-2H1]-homocitrates and dimethyl (2S,3R)- and (2R,3R)-[2-2H1]-homocitrate lactones—an assay for the stereochemical outcome of the reaction catalysed both by homocitrate synthase and by the Nif-V protein

    A. Tavassoli, J. E. S. Duffy and D. W. Young, Org. Biomol. Chem., 2006, 4, 569
    DOI: 10.1039/B515937G

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