A mechanistic investigation of the microbial chiral inversion of 2-phenylpropionic acid by Verticillium lecanii

Chirality
M J ThomasonA W Lloyd

Abstract

Previous investigations have described the development of nongrowing suspensions of Verticillium lecanii as a microbial model of the mammalian chiral inversion of the 2-arylpropionic acids (2-APAs). Mechanistic studies in mammals have shown that inversion involves loss of the alpha-methine proton but retention of the original atoms at the beta-methyl position, and a mechanism has been proposed involving enzymatic epimerisation of acyl-CoA thioester derivatives of the substrate. Inversion of the 2-APAs by V. lecanii exhibits extensive intersubstrate variation in the presence, rate, extent, and direction of inversion, which are different from those observed in mammalian systems, possibly indicating differences in the mechanism of inversion between mammalian and microbial cells. This study involved the investigation of proton/deuterium exchange by 1H-nuclear magnetic resonance following incubation of deuterated derivatives of 2-phenylpropionic acid (2-PPA), a model compound, in cell suspensions of V. lecanii and incubation of undeuterated 2-PPA in cell suspensions containing D2O. The results indicated that the inversion of 2-PPA by V. lecanii also involved exchange of the alpha-methine proton but complete retention of the original...Continue Reading

References

Nov 1, 1975·Journal of Pharmaceutical Sciences·R V Smith, J P Rosazza
Jul 1, 1992·European Journal of Drug Metabolism and Pharmacokinetics·V RossettiE Gadoni
Jan 1, 1990·Fundamental & Clinical Pharmacology·N MullerP Netter
Apr 1, 1985·Medicinal Research Reviews·A M ClarkC D Hufford
Dec 11, 1974·Biochemical and Biophysical Research Communications·W J WechterD G Kaiser
Nov 1, 1983·The Journal of Pharmacy and Pharmacology·A J Hutt, J Caldwell

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Citations

Mar 1, 1997·The Journal of Pharmacy and Pharmacology·M J ThomasonG W Hanlon

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