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Pergamon Tetrahedron: Asymmetry 10 (1999) 28332843 Biocatalytic and chemical routes to all the stereoisomers of
 

Summary: Pergamon Tetrahedron: Asymmetry 10 (1999) 28332843


Biocatalytic and chemical routes to all the stereoisomers of
methionine and ethionine sulfoxides
Herbert L. Holland,
Peter R. Andreana and Frances M. Brown
Department of Chemistry, Brock University, St. Catharines, ON L2S 3A1, Canada
Received 27 April 1999; accepted 15 June 1999
Abstract
Biotransformations of the N-phthaloyl derivatives of D- and L-methionine and of D- and L-ethionine by
Beauveria bassiana ATCC 7159 or Beauveria caledonica ATCC 64970 produce the corresponding (SS) sulfoxides
in good yield and diastereomeric excess. Pure (SSSC) diastereomers can be obtained from L-series substrates by
crystallisation of the biotransformation extract, and the corresponding (SSRC) products obtained from D-series
substrates by chromatography of the biotransformation extract. Hydrogen peroxide-catalysed oxidation of the N-
phthaloyl derivatives of D- and L-methionine and of D- and L-ethionine gives diastereomeric mixtures from which
the (SSSC) and (RSRC) diastereomers can be obtained by crystallisation, and the (SSRC) and (RSSC) diastereomers
obtained by chromatography. N-Cbz- and N-t-Boc methionines are also converted to sulfoxides with predominant
(SS) configuration by both B. bassiana and B. caledonica, but the isolated yields and d.e. of products were generally
lower than those obtained from the N-phthaloyl substrates.

  

Source: Andreana, Peter R. - Department of Chemistry, Wayne State University

 

Collections: Chemistry