Synthesis of (2R)- (2S)- [1-13C]-2-amino-2-methylmalonic acid: chiral substrates for serine hydroxymethyltransferase

  • Thomas N
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Abstract

(2R) - and (2S)-[1-C-13]-2-amino-2-methylmalonate, probes for the stereochemical course of the serine hydroxymethyltransferase reaction, have been synthesised from bis-lactim ethers derived from valine and alanine. Direct acylation of the anion with diethyl carbonate gave the N-ethoxycarbonyl derivative rather than the required ethyl ester. The C-13-labelled carboxyl group was therefore introduced via treatment of the anion with [1-C-13]-acetyl chloride, followed by haloform oxidation. The resulting carboxylate salt was then esterified with methyl iodide, and the bis-lactim ether ring system was cleaved under acidic conditions to give the amino acid esters. Saponification and then separation by cation exchange chromatography gave the title compounds.

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Thomas, N. R. (1991). Synthesis of (2R)- (2S)- [1-13C]-2-amino-2-methylmalonic acid: chiral substrates for serine hydroxymethyltransferase. Tetrahedron, 47(3), 497–506.

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