188906-20-9Relevant academic research and scientific papers
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.
Synthesis and enzyme-catalysed reductions of 2-oxo acids with oxygen containing side-chains
Bhalay, Gurdip,Clough, Sarah,McLaren, Lee,Sutherland, Andrew,Willis, Christine L.
, p. 901 - 910 (2007/10/03)
A series of novel 2-oxo esters with protected alcohols at the 3-, 4-, 5-, 6- and 7-positions has been prepared either via coupling of an aldehyde with an organometallic reagent (Zn, In or Cr) or via a one-carbon homologation of the precursor acid. A one-pot dual enzyme system was used to convert the simpler 2-oxo acids (with a single MOM ether at either C-3 or C-4) into enantiopure protected 2,3- and 2,4-dihydroxy acids in good yields, but in the cases of the more complex trisubstituted substrates, significant decomposition occurred. Biotransformations have proved valuable for the enantioselective synthesis of protected 2,6,7-trihydroxyhept-3-enoic acids.
