188906-20-9Relevant articles and documents
Enantioselective syntheses of α-amino-β-hydroxy acids, [15N]-L-allothreonine and [15N]-L-threonine
Sutherland, Andrew,Willis, Christine L.
, p. 1837 - 1840 (1997)
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.
