Synthesis of trimethyl (2S,3R)- and (2R,3R)-[2-H-2(1)]-homocitrates the corresponding dimethyl and ester lactones: towards elucidating the stereochemistry of the reaction catalysed by homocitrate synthase and by the Nif-V protein

Tavassoli, Ali, Duffy, James E.S. and Young, Douglas W. (2005) Synthesis of trimethyl (2S,3R)- and (2R,3R)-[2-H-2(1)]-homocitrates the corresponding dimethyl and ester lactones: towards elucidating the stereochemistry of the reaction catalysed by homocitrate synthase and by the Nif-V protein. Tetrahedron Letters, 46 (12), 2093-2096. (doi:10.1016/j.tetlet.2005.01.134).

Record type: Article

Abstract

Trimethyl (2S,3R)- and (2R,3R)-[2-H-2(1)]-homocitrates, 10b and 10c respectively, and dimethyl (2S,3R)- and (2R,3R)[2 [2-H-2(1)]-homocitric lactones, 11b and 11c respectively, have been synthesised from shikimic acid and [2-H-2]-shikimic acid by a route which defines the stereochemistry of the two chiral centres in each compound. The NMR spectra of these products will enable the stereochemistry of the biological reaction catalysed by homocitrate synthase and by the protein from the nifV gene to be elucidated.

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Published date: 2005

Keywords: enzymes synthesis stereospecific homocitrate shikimate enantiospecific synthesis lysine biosynthesis citrate synthase d-mannose acid hydroperoxide intermediate epoxidations alcohols

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