316823-17-3Relevant academic research and scientific papers
Syntheses of isotopically labelled L-?±-amino acids with an asymmetric centre at C-3
Harding, John R.,Hughes, Rachael A.,Kelly, Nicholas M.,Sutherland, Andrew,Willis, Christine L.
, p. 3406 - 3416 (2007/10/03)
Approaches are described to the synthesis of a series of isotopically labelled L-a-amino acids each with an asymmetric centre at C-3, including isoleucine, allo-isoleucine, threonine and allo-threonine. The methods may be simply adapted for the selective incorporation of an isotopic label at each site of L-valine including the selective labelling of either diastereotopic methyl group with carbon-13 and/or deuterium and labelling of the amine with nitrogen-15. ? The Royal Society of Chemistry 2000.
Enantioselective syntheses of α-amino-β-hydroxy acids, [15N]-L-allothreonine and [15N]-L-threonine
Sutherland, Andrew,Willis, Christine L.
, p. 1837 - 1840 (2007/10/03)
The enantioselective synthesis of [15N]-L-allothreonine from ethyl (S)-lactate via methyl (S)-3-methoxymethoxy-2-oxobutanoate 15 is described. The stereogenic centre at C-2 was established by a one-pot, dual enzyme catalysed hydrolysis of the ester (by a lipase) and reductive amination of the ketone of 15 (with leucine dehydrogenase) to give, after deprotection, [15N]-(2S,3S)-2-amino-3-hydroxybutanoic acid as a single diastereomer in 93% yield. [15N]-L-Threonine was prepared by an analogous strategy from methyl (R)-lactate using phenylalanine dehydrogenase in the reductive amination step. This approach may be simply adapted for the incorporation of deuterium and carbon-13.
