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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
Author(s) -
Felluga Fulvia,
Fermeglia Maurizio,
Ferrone Marco,
Pitacco Giuliana,
Pricl Sabrina,
Valentin Ennio
Publication year - 2002
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(200211)85:11<4046::aid-hlca4046>3.0.co;2-f
Subject(s) - chemistry , absolute configuration , enantiomer , diastereomer , stereochemistry , moiety , carboxylate , lactam , chymotrypsin , enzyme , acetone , resolution (logic) , lactone , organic chemistry , trypsin , artificial intelligence , computer science
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.