Enzymic kinetic resolution of .alpha.-nitro .alpha.-methyl carboxylic acids Academic Article uri icon

abstract

  • Synthetic routes to various quaternary α-nitro α-methyl carboxylic acid esters from simpler nitroalkanes and nitroalkane derivatives are described. These quaternary α-amino acid precursors can be kinetically resolved by using α-chymotrypsin. It was found that partial hydrolysis of these αnitro α-methyl esters and recovery of the unhydrolyzed ester proceeds preferentially by hydrolysis of the D enantiomer. Reduction of the α-nitro group thus then affords highly enantiomerically enriched L-α-methyl α-amino acids. © 1988, American Chemical Society. All rights reserved.

author list (cited authors)

  • Lalonde, J. J., Bergbreiter, D. E., & Wong, C. H.

citation count

  • 56

publication date

  • May 1988