860012-01-7Relevant academic research and scientific papers
Studies on enzymatic synthesis of chiral non-racemic 3-arylglutaric acid monoesters
Fryszkowska, Anna,Komar, Marta,Koszelewski, Dominik,Ostaszewski, Ryszard
, p. 961 - 966 (2007/10/03)
The enantioselective enzymatic desymmetrization (EED) of various 3-arylglutaric anhydrides 1 with alcohols in organic media has been studied. The effect of the solvent on the stereochemical outcome of the reaction was investigated in detail. The amount of biocatalyst was optimized, and the possibility of its re-use was tested. The first example of the EED of 3-substituted glutaric anhydrides with esters as nucleophiles is reported.
One-pot enzymatic desymmetrization and Ugi MCR
Fryszkowska, Anna,Frelek, Jadwiga,Ostaszewski, Ryszard
, p. 6064 - 6072 (2007/10/03)
A new approach to the synthesis of chiral peptidomimetics is reported. It combines an enzymatic desymmetrization of 3-phenylglutaric anhydrides with a subsequent Ugi multi-component reaction in a one-pot, two-step procedure. NMR and CD spectroscopy was used to assign the configurations of obtained products. Our synthetic method is very efficient and it can easily be extended to other types of multi-component reactions and can be used for the preparation of chiral peptidomimetic libraries.
Enzymatic desymmetrization of 3-arylglutaric acid anhydrides
Fryszkowska, Anna,Komar, Marta,Koszelewski, Dominik,Ostaszewski, Ryszard
, p. 2475 - 2485 (2007/10/03)
Optically active (R)- and (S)-3-arylglutaric acid monoesters 3 were synthesized in quantitative yields and good stereoselectivities by lipase-catalyzed desymmetrization of the corresponding 3-arylglutaric anhydrides 2 with alcohols. It was observed that the stereochemical outcome of the reaction was influenced by the substituents present on the aromatic ring. The influence of the enzyme, alcohol, and solvent was systematically examined. Absolute configurations of the monoesters 3 were assigned by chemical correlation to corresponding lactones 4.
