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- Title
Chemo-Enzymatic Synthesis and Determination of the Absolute Configuration of Both Enantiomers of Methyl trans-5-Oxo-2-pentylpyrrolidine-3-carboxylate Precursors of the Aza Analogues of (+)- and (−)-Methylenolactocin.
- Authors
Felluga, Fulvia; Fermeglia, Maurizio; Ferrone, Marco; Pitacco, Giuliana; Pricl, Sabrina; Valentin, Ennio
- Abstract
Enantiomerically pure methyl esters of (+)-(2 R,3 S)- and (−)-(2 S,3 R)-5-oxo-2-pentylpyrrolidine-3-carboxylic acid with 99% and 98% ee were obtained by enzymatic resolution of the corresponding racemic mixture using α-chymotrypsin and pig-liver acetone powder, respectively. Their absolute configurations were established by chemical methods, i.e., conversion of the trans- γ-lactam moiety to the corresponding γ-lactone of known configuration. The favorable interactions between the trans- γ-lactam and α-chymotrypsin were rationalized by molecular-mechanics calculations, which suggest a different situation for the cis-diastereoisomer.
- Publication
Helvetica Chimica Acta, 2002, Vol 85, Issue 11, p4046
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/1522-2675(200211)85:11<4046::AID-HLCA4046>3.0.CO;2-F