Enzymatic synthesis of chiral organophosphothioates from prochiral precursors. Academic Article uri icon

abstract

  • The phosphotriesterase from Pseudomonas diminuta has been shown to selectively cleave the pro-R p-nitrophenolate substituent from bis-p-nitrophenyl alkyl phosphothioate esters. When the alkyl substituent is methyl, ethyl, or isopropyl the enantiomeric excess of the product is >/=99%. Manipulation of the active site through mutagenesis has enabled the preparation of protein variants that preferentially hydrolyze the pro-S substituent of the target substrates. This methodology thus permits the preparation of chiral products from prochiral precursors.

author list (cited authors)

  • Li, W., Li, Y., Hill, C. M., Lum, K. T., & Raushel, F. M

complete list of authors

  • Li, Wen-Shan||Li, Yingchun||Hill, Craig M||Lum, Karin T||Raushel, Frank M

publication date

  • January 1, 2002 11:11 AM