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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 

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Efficient chemoenzymatic synthesis of pelitrexol via enzymic differentiation of a remote stereocenter.

[structure: see text] An efficient chemoenzymatic process is described for the synthesis of pelitrexol, a novel GARFT inhibitor. The remoteness of this molecule's stereocenter in the tetrahydropterin moiety from the terminal carbonyl group provided a significant challenge in synthesis. The introduction of an oxalamic ester adjacent to the stereocenter dramatically enhanced an enzyme's enantioselectivity for hydrolysis at the terminal ester, producing the desired S-acid with high optical purity and yield. The recycling of the "wrong" enantiomer is achieved via a dehydrogenation/hydrogenation strategy.[1]

References

  1. Efficient chemoenzymatic synthesis of pelitrexol via enzymic differentiation of a remote stereocenter. Hu, S., Kelly, S., Lee, S., Tao, J., Flahive, E. Org. Lett. (2006) [Pubmed]
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